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Cas Database




  • Product Name:Benzylamine

  • CAS Number: 100-46-9

  • EINECS:202-854-1

  • Molecular Weight:107.155

  • Molecular Formula: C7H9N

  • HS Code:2921 49 00

  • Mol File:100-46-9.mol

Synonyms:phenylmethanamine;1-phenylmethanamine;Monobenzylamine;.omega.-Aminotoluene;benzylazanium;(Phenylmethyl)amine;benzenemethanamine;.alpha.-Aminotoluene;Benzylamine(BA);Benzyl amine;N-Benzylamine;Benzylamine 99%;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC

  • Hazard Codes:C

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH312 Harmful in contact with skin H314 Causes severe skin burns and eye damage

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Refer for medical attention . Inhalation of vapor causes irritation of the mucous membranes of the nose and throat, and lung irritation with respiratory distress and cough. Headache, nausea, faintness, and anxiety can occur. Exposure to vapor produces eye irritation with lachrymation, conjunctivitis, and corneal edema resulting in halos around lights. Direct local contact with liquid is known to produce severe and sometimes permanent eye damage and skin burns. Vapors may also produce primary skin irritation and dermatitis. (USCG, 1999) /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic bases/Amines and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Powder, alcohol-resistant foam, water spray, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Special Hazards of Combustion Products: Toxic nitrogen oxides may form in a fire. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: complete protective clothing including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Cautiously neutralize remainder. Then wash away with plenty of water. SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from strong oxidants, strong acids and food and feedstuffs.Fireproof. Separated from strong oxidants, strong acids, food and feedstuffs.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:AK Scientific
  • Product Description:Benzylamine
  • Packaging:4x25mL
  • Price:$ 40
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  • Manufacture/Brand:AK Scientific
  • Product Description:Benzylamine
  • Packaging:4x25mL
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:Benzylamine, 98+%
  • Packaging:500g
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:Benzylamine, 98+%
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:Benzylamine, 98+%
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:Benzylamine, 98+%
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  • Manufacture/Brand:Apolloscientific
  • Product Description:Benzylamine 98+%
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  • Manufacture/Brand:Apolloscientific
  • Product Description:Benzylamine 98+%
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  • Product Description:Benzylamine 98+%
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Relevant articles and documentsAll total 626 Articles be found

Preparation and characterization of primary amines by potassium borohydride-copper chloride system from nitriles

Jiang, Han,Hu, Jialei,Xu, Xinliang,Zhou, Yifeng

, p. 3564 - 3566 (2015)

Nitriles undergo reduction to primary amines under optimized conditions at 50 °C using 0.25 equiv of copper chloride and 3.0 equiv of potassium borohydride in 80 % isopropanol. The aromatic and aralkyl nitriles could be effectively reduced in yield ranging from 60 to 90 %.

Catalytic transamidation under moderate conditions

Eldred, Sarah E.,Stone, David A.,Gellman, Samuel H.,Stahl, Shannon S.

, p. 3422 - 3423 (2003)

The carboxamide group is generally inert, except under harsh conditions or in the presence of highly evolved enzymes. We have identified several metal complexes that efficiently catalyze transamidation reactions of amide/amine mixtures under moderate cond

Electronic Effect of Ruthenium Nanoparticles on Efficient Reductive Amination of Carbonyl Compounds

Komanoya, Tasuku,Kinemura, Takashi,Kita, Yusuke,Kamata, Keigo,Hara, Michikazu

, p. 11493 - 11499 (2017)

Highly selective synthesis of primary amines over heterogeneous catalysts is still a challenge for the chemical industry. Ruthenium nanoparticles supported on Nb2O5 act as a highly selective and reusable heterogeneous catalyst for the low-temperature reductive amination of various carbonyl compounds that contain reduction-sensitive functional groups such as heterocycles and halogens with NH3 and H2 and prevent the formation of secondary amines and undesired hydrogenated byproducts. The selective catalysis of these materials is likely attributable to the weak electron-donating capability of Ru particles on the Nb2O5 surface. The combination of this catalyst and homogeneous Ru systems was used to synthesize 2,5-bis(aminomethyl)furan, a monomer for aramid production, from 5-(hydroxymethyl)furfural without a complex mixture of imine byproducts.



, p. 335 (1972)


A Mild and Base-Free Protocol for the Ruthenium-Catalyzed Hydrogenation of Aliphatic and Aromatic Nitriles with Tridentate Phosphine Ligands

Adam, Rosa,Bheeter, Charles Beromeo,Jackstell, Ralf,Beller, Matthias

, p. 1329 - 1334 (2016)

A novel protocol for the general hydrogenation of nitriles in the absence of basic additives is described. The system is based on the combination of [Ru(cod)(methylallyl)2] (cod=cyclooctadiene) and L2. A variety of aromatic and aliphatic nitriles is hydrogenated under mild conditions (50 °C and 15 bar H2) with this system. Kinetic studies revealed higher activity in the case of aromatic nitriles compared with aliphatic ones.


Weinreb, Steven M.,Demko, Donald M.,Lessen, Thomas A.,Demers, James P.

, p. 2099 - 2102 (1986)

The title compound, easily prepared in two steps from vinyltrimethylsilane, is a useful reagent for the protection of primary and secondary amines as their sulfonamides, which are cleaved by fluoride ion.

Total synthesis of capsaicin analogues from lignin-derived compounds by combined heterogeneous metal, organocatalytic and enzymatic cascades in one pot

Anderson, Mattias,Afewerki, Samson,Berglund, Per,Cordova, Armando

, p. 2113 - 2118 (2014)

The total synthesis of capsaicin analogues was performed in one pot, starting from compounds that can be derived from lignin. Heterogeneous palladium nanoparticles were used to oxidise alcohols to aldehydes, which were further converted to amines by an enzyme cascade system, including an amine transaminase. It was shown that the palladium catalyst and the enzyme cascade system could be successfully combined in the same pot for conversion of alcohols to amines without any purification of intermediates. The intermediate vanillylamine, prepared with the enzyme cascade system, could be further converted to capsaicin analogues without any purification using either fatty acids and a lipase, or Schotten-Baumann conditions, in the same pot. An aldol compound (a simple lignin model) could also be used as starting material for the synthesis of capsaicin analogues. Using L-alanine as organocatalyst, vanillin could be obtained by a retro-aldol reaction. This could be combined with the enzyme cascade system to convert the aldol compound to vanillylamine in a one-step one-pot reaction.

Ruthenium(II)-cored supramolecular organic framework-mediated recyclable visible light photoreduction of azides to amines and cascade formation of lactams

Wu, Yi-Peng,Yan, Meng,Gao, Zhong-Zheng,Hou, Jun-Li,Wang, Hui,Zhang, Dan-Wei,Zhang, Junliang,Li, Zhan-Ting

, p. 1383 - 1386 (2019)

Ru(bpy)3]2+-cored supramolecular organic framework SMOF-1, assembled from a [Ru(bpy)3]2+-derived hexaarmed molecule and cucurbit[8]uril, has been demonstrated to heterogeneously catalyze visible light-induced reduction of phenyl, benzyl, 2-phenylethyl and 3-phenylpropyl azides in acetonitrile to produce the corresponding amines in good to high yields. For the last two kinds of azides that bear a CO2Me group at the para-position of the benzene ring, cascade reactions take place to generate the corresponding lactams in high yields. Compared with homogeneous control [Ru(bpy)3]Cl2, SMOF-1 exhibits remarkably increased photocatalysis activity as a result of synergistic effect of the [Ru(bpy)3]2+ units that form cubic cages to host the azide molecules and related intermediates. Moreover, SMOF-1 displays high recyclability and considerable photocatalysis activity after 3 to 12 runs.

Tandem dehydrogenation of ammonia borane and hydrogenation of nitro/nitrile compounds catalyzed by graphene-supported NiPd alloy nanoparticles

Goeksu, Haydar,Ho, Sally Fae,Metin, Oender,Korkmaz, Katip,Mendoza Garcia, Adriana,Gueltekin, Mehmet Serdar,Sun, Shouheng

, p. 1777 - 1782 (2014)

We report a facile synthesis of monodisperse NiPd alloy nanoparticles (NPs) and their assembly on graphene (G) to catalyze the tandem dehydrogenation of ammonia borane (AB) and hydrogenation of R-NO2 and/or R-CN to R-NH2 in aqueous methanol solutions at room temperature. The 3.4 nm NiPd alloy NPs were prepared by coreduction of nickel(II) acetate and palladium(II) acetlyacetonate by borane-tert-butylamine in oleylamine and deposition on G via a solution phase self-assembly process. G-NiPd showed composition-dependent catalysis on the tandem reaction with G-Ni 30Pd70 being the most active. A variety of R-NO 2 and/or R-CN derivatives were reduced selectively into R-NH 2 via G-Ni30Pd70 catalyzed tandem reaction in 5-30 min reaction time with the conversion yields reaching up to 100%. Our study demonstrates a new approach to G-NiPd-catalyzed dehydrogenation of AB and hydrogenation of R-NO2 and R-CN. The G-NiPd NP catalyst is efficient and reusable, and the reaction can be performed in an environment-friendly process with short reaction times and high yields.

Reductive amination of furfural to furfurylamine using aqueous ammonia solution and molecular hydrogen: An environmentally friendly approach

Chatterjee, Maya,Ishizaka, Takayuki,Kawanami, Hajime

, p. 487 - 496 (2016)

A simple and highly efficient method was developed for the transformation of furfural (a biomass derived aldehyde) to furfurylamine by reductive amination using an aqueous solution of ammonia and molecular hydrogen as an amine source and a reducing agent, respectively. By choosing a suitable catalyst, such as Rh/Al2O3, and reaction conditions, a very high selectivity of furfurylamine (~92%) can be achieved within the reaction time of 2 h at 80 °C. A detailed analysis of the reaction system sheds some light on the reaction pathway and provides an understanding about each elementary step. The reaction was believed to proceed via an imine pathway although no such intermediate was detected because of the highly reactive nature. Optimization of different reaction parameters such as hydrogen pressure, temperature and substrate/ammonia mole ratio is shown to be critical to achieve high selectivity of furfurylamine. Time-dependent reaction profiles suggested that a Schiff base type intermediate was in the detectable range, which offers indirect evidence of the formation of imine. Competitive hydrogenation and amination of an aldehyde group were strongly dictated by the nature of the metal used. The studied protocol represents an environmentally benign process for amine synthesis, which can be effectively extended to the other aldehydes also. The studied catalyst could be recycled successfully without any significant loss of catalytic activity.

A Pd/CeO2 “H2 Pump” for the Direct Amination of Alcohols

Yan, Zhen,Tomer, Ajay,Perrussel, Gaetan,Ousmane, Mohamad,Katryniok, Benjamin,Dumeignil, Franck,Ponchel, Anne,Liebens, Armin,Pera-Titus, Marc

, p. 3347 - 3352 (2016)

A Pd/CeO2 catalyst with a prominent reversible H2 storage capacity revealed a high activity and selectivity in the direct amination of benzyl alcohol with aniline and ammonia via the borrowing hydrogen mechanism.

Mesoporous silicabis(ethylsulfanyl)propane palladium catalysts for hydrogenation and one-pot two-step Suzuki cross-coupling followed by hydrogenation

Qazi, Asma,Sullivan, Alice

, p. 10637 - 10642 (2011)

The solid phase catalytic activity of mesoporous silicabis(ethylsulfanyl) propane palladium catalysts for hydrogenation and novel one-pot two-step Suzuki cross-coupling followed by hydrogenation is described. The efficiency of catalytic hydrogenation was measured for substrate nitrobenzene with 5, 7 and 14 nm average pore diameter materials. The 5 nm pore material performed best and was also very effective in the catalytic hydrogenation of alkene, nitrile and imine substrates. Novel one-pot two-step Suzuki cross-coupling and hydrogenation was demonstrated using bromonitro- and bromodinitrobenzene and phenylboronic acid as substrates with conversion to the corresponding coupled amino compounds. As a consequence of the high affinity of the sulfur ligands for palladium, none was detected in leaching tests and the catalyst is easily separated and recycled.

Synthesis of new Copper Catalyst with Pyrazole Based Tridentate Ligand and Study of Its Activity for Azide Alkyne Coupling

Rajeswari, Panneer Selvam,Nagarajan, Rajendran,P, Sujith K,Emmanuvel, Lourdusamy

, (2021)

Synthesis of new copper catalyst with pyrazole based tridentate ligand and study of its activity for azide alkyne coupling were investigated by researchers. To a solution of acetyl acetone (2.002 g, 20 mmol), 2- nitrophenylhydrazine in ethanol was added five drops of con. HCl and heated at 50° for 1 hour. After confirming the formation of 3, 5-dimethyl-1-(2-nitrophenyl)- 1H-pyrazole by TLC, ice cooled water was added in to the reaction mixture. The precipitate was filtered, washed with water and then hexane. The product formed as yellow precipitate, that precipitate had been filtered by normal filter paper. The product was recrystallized in ethanol. For synthesis, was suspended in 6 mL of deionized and stirred for 4 h until a clear solution was obtained in 50 ml round bottom flask Cu(OAc) 2. The reaction mixture was diluted with water, filtered, washed sequentially with water, methanol and n-hexane. Then dark greenish blue color crystal were formed and used for the reactions. The solid was crystallized in CH2Cl2 to get crystal whose structure was confirmed by single crystal XRD.

Application of hydrazinium monoformate as new hydrogen donor with Raney nickel: A facile reduction of nitro and nitrile moieties

Gowda, Shankare,Gowda, D.Channe

, p. 2211 - 2213 (2002)

The nitro groups in aliphatic and aromatic nitrocompounds also containing reducible substituents such as ethene, acid, phenol, halogen, ester etc., are rapidly reduced at room temperature to corresponding amines by employing hydrazinium monoformate, a new hydrogen donor, in the presence of Raney nickel. It was observed that the nitrile function also undergoes reduction to methylamine (-CH2-NH2). Hydrazinium monoformate is a more effective donor than hydrazine or formic acid and reduction of nitro and nitrile groups occurs without hydrogenolysis in the presence of low cost Raney nickel, compared to expensive metals like palladium, platinum or ruthenium. The reduction is reasonably fast, clean and high yielding.

The reduction of aromatic oximes to amines with borohydride exchange resin-nickel acetate system


, p. 863 - 869 (1995)

Aromatic oximes were reduced to the corresponding amines with borohydride supported on an ion exchange resin (BER)- nickel acetate in methanol in good yields. The isolation of pure products by simple filtration and evaporation is an important feature of this method.

Structure-Function Relationship in Ester Hydrogenation Catalyzed by Ruthenium CNN-Pincer Complexes

Le, Linh,Liu, Jiachen,He, Tianyi,Kim, Daniel,Lindley, Eric J.,Cervarich, Tia N.,Malek, Jack C.,Pham, John,Buck, Matthew R.,Chianese, Anthony R.

, p. 3286 - 3297 (2018)

A series of six pincer-ruthenium complexes has been synthesized and applied in the catalytic hydrogenation of esters. The ruthenium complexes have the formula Ru(pincer)HCl(CO), where the CNN-pincer ligands feature N-heterocyclic carbene (NHC), pyridine, and dialkylamino donor groups. Through systematic variation of the steric bulk of the NHC substituent and the amine substituents, a clear structure-function relationship emerges. The most active catalysts in this series feature the bulkiest NHC substituent employed, 2,6-diisopropylphenyl. For the dialkylamino group, catalysts substituted with isopropyl or ethyl groups were the most active, while catalysts substituted with methyl groups were significantly less active. The most active catalyst discovered catalyzes the complete hydrogenation of a range of esters at loadings of 0.05-0.2 mol %.

Reduction of Azides to Amines with Sodium Borohydride in Tetrahydrofuran with Dropwise Addition of Methanol

Soai, Kenso,Yokoyama, Shuji,Ookawa, Atsuhiro

, p. 48 - 49 (1987)

Azidoalkanes, azidoarenes, and tosyl azide are reduced to the corresponding amines or p-toluenesulfonamide, respectively, by reaction with sodium borohydride in tetrahydrofuran with dropwise addition of small amounts of methanol.

Photoinduced Alcoholysis of Trihaloacetyl Group

Izawa, Yasuji,Ishiguro, Katsuhiro,Tomioka, Hideo

, p. 951 - 952 (1983)

Photolysis of trichloroacetamide in nondegassed methanol gave methyl oxanilate (13-44percent), along with carbamate (3-20percent) and amine (4-12percent).Similar irradiation of other trichloroacetylderivatives of aliphatic ketone, aldehyde, and acetate afforded only radical product.The results are interpreted in terms of the mechanism involving electron transfer of the radical pair.

Platinum-(phosphinito-phosphinous acid) complexes as bi-talented catalysts for oxidative fragmentation of piperidinols: An entry to primary amines

Membrat, Romain,Vasseur, Alexandre,Moraleda, Delphine,Michaud-Chevallier, Sabine,Martinez, Alexandre,Giordano, Laurent,Nuel, Didier

, p. 37825 - 37829 (2019)

Platinum-(phosphinito-phosphinous acid) complex catalyzes the oxidative fragmentation of hindered piperidinols according to a hydrogen transfer induced methodology. This catalyst acts successively as both a hydrogen carrier and soft Lewis acid in a one pot-two steps process. This method can be applied to the synthesis of a wide variety of primary amines in a pure form by a simple acid-base extraction without further purification.

Reductive debenzylation of hexabenzylhexaazaisowurtzitane

Bellamy, Anthony J.

, p. 4711 - 4722 (1995)

The reductive debenzylation of hexabenzylhexaazaisowurtzitane (2) under a wide variety of hydrogenation conditions has been investigated. Hydrogenation of 2 in acetic anhydride gives the tetraacetyl dibenzyl derivative 3 as the final product. Further acet

Pyridonate-Supported Titanium(III). Benzylamine as an Easy-To-Use Reductant

Chong, Eugene,Xue, Wei,Storr, Tim,Kennepohl, Pierre,Schafer, Laurel L.

, p. 4941 - 4945 (2015)

The reaction of bis(3-phenyl-2-pyridonate)Ti(NMe2)2 with excess benzylamine leads to an unexpected reduction of the metal center from Ti(IV) to Ti(III). The reduced titanium species was isolated and revealed as tris(3-phenyl-2-pyrido


Kajiwara et al.

, p. 967 (1978)


Mild catalytic deoxygenation of amides promoted by thorium metallocene

Eisen, Moris S.,Saha, Sayantani

, p. 12835 - 12841 (2020)

The organoactinide-catalyzed (Cp*2ThMe2) hydroborated reduction of a wide range of tertiary, secondary, and primary amides to the corresponding amines/amine-borane adductsviadeoxygenation of the amides is reported herein. The catalytic reactions proceed under mild conditions with low catalyst loading and pinacolborane (HBpin) concentration in a selective fashion. Cp*2ThMe2is capable of efficiently catalysing the gram-scale reaction without a drop in efficiency. The amine-borane adducts are successfully converted into free amine products in high conversions, which increases the usefulness of this catalytic system. A plausible mechanism is proposed based on detailed kinetics, stoichiometric, and deuterium labeling studies.



, p. 253,254,256 (1955)


Molecular Addition Compounds. 11. N-Ethyl-N-isopropylaniline-Borane, a Superior Reagent for Hydroborations and Reductions

Brown, Herbert C.,Kanth, J. V. Bhaskar,Zaidlewicz, Marek

, p. 5154 - 5163 (1998)

Hydroboration studies with a new, highly reactive amine-borane adduct, H3B-NPhEtPri, and representative olefins, such as 1-hexene, styrene, β-pinene, cyclopentene, norbornene, cyclohexene, 2-methyl-2-butene, α-pinene, and 2,3-dimethyl-2-butene, in tetrahydrofuran, dioxane, tert-butyl methyl ether, n-pentane, and dichloromethane, at room temperature (22 ± 3°C) were carried out. The reactions are faster in dioxane, requiring 0.5-1 h for the hydroboration of simple, unhindered olefins to the trialkylborane stage. Moderately hindered olefins, such as cyclohexene and 2-methyl-2-butene, give the corresponding dialkylboranes rapidly, with further hydroboration slow. However, the hindered α-pinene and 2,3-dimethyl-2-butene structures give stable monoalkylboranes very rapidly, with further hydroboration proceeding relatively slowly. The hydroborations can also be carried out in other solvents, such as THF, tert-butyl methyl ether, and n-pentane. A significant rate retardation is observed in dichloromethane. Regioselectivity studies in the hydroboration of 1-hexene, styrene, and allyl chloride with H3B-NPhEtPri in selected solvents were made. The selectivities are similar to those reported for BH3-THF with 1-hexene and styrene, whereas some differences were noted for allyl chloride. The alkylboranes obtained after hydroboration were oxidized with hydrogen peroxide/sodium hydroxide, and the product alcohols were obtained in quantitative yields, as established by GC analysis. The rates and stoichiometry of the reaction of H3B-NPhEtPri in tetrahydrofuran with selected organic compounds containing representative functional groups were examined at room temperature. Simple aldehydes, ketones, carboxylic acids, and aliphatic esters were reduced to the alcohol stage. Acid chlorides, anhydrides, and aromatic carboxylic esters were unreactive under similar conditions. Imines, tertiary amides, and nitriles were reduced to the corresponding amines. However, primary and secondary amides and nitro compounds were not reduced under these conditions. The reduction of esters, amides, and nitriles, which exhibit a sluggish reaction at room temperature, proceeds readily under reflux conditions in tetrahydrofuran and dioxane and also without solvent (at 85-90°C). The carrier amine was recovered by simple acid-base manipulations in good yield and can be readily recycled to make the borane adduct.



, p. 162 (1911)


A Mild and Convenient Reduction of Aromatic and Heteroaromatic Aldoximes with Ammonium Formate/Pd

Kaczmarek, Lukasz,Balicki, Roman

, p. 695 - 697 (1994)


Easy access to Ni3N- and Ni-carbon nanocomposite catalysts

Clavel, Guylhaine,Molinari, Valerio,Kraupner, Alexander,Giordano, Cristina

, p. 9018 - 9023 (2014)

In the search for alternative materials to current expensive catalysts, Ni has been addressed as one of the most promising and, on this trail, its corresponding nitride. However, nickel nitride is a thermally unstable compound, and therefore not easy to prepare especially as nanoparticles. In the present work, a sol-gel-based process (the urea glass route) is applied to prepare well-defined and homogeneous Ni3N and Ni nanoparticles. In both cases, the prepared crystalline nanoparticles (~25 nm) are dispersed in a carbon matrix forming interesting Ni3N- and Ni-based composites. These nanocomposites were characterised by means of several techniques, such as XRD, HR-TEM, EELS, and the reaction mechanism was investigated by TGA and IR and herein discussed. The catalytic activity of Ni3N is investigated for the first time, to the best of our knowledge, for hydrogenation reactions involving H2, and here compared to the one of Ni. Both materials show good catalytic activities but, interestingly, give a different selectivity between different functional groups (namely, nitro, alkene and nitrile groups). A nickel for every time: Homogeneous Ni3N and Ni nanoparticles embedded in a carbon matrix were prepared by the urea glass route. Their respective catalytic activities over different functional groups are reported for hydrogenation reactions using H2 (see scheme).

The efficient solvent-free reduction of oximes to amines with NaBH3CN catalyzed by ZrCl4/nano Fe3O4 system

Sadighnia, Leila,Zeynizadeh, Behzad

, p. 873 - 878 (2015)

Reduction of various aldoximes and ketoximes to the corresponding amines was carried out easily and efficiently with NaBH3CN in the presence of ZrCl4/nano Fe3O4 system. The reactions were carried out under solvent-free conditions at room temperature or 75-80°C to afford amines in high to excellent yields.

Reduction of nitriles to amines with H2 catalyzed by nonclassical ruthenium hydrides - Water-promoted selectivity for primary amines and mechanistic investigations

Gunanathan, Chidambaram,Hoelscher, Markus,Leitner, Walter

, p. 3381 - 3386 (2011)

Catalytic hydrogenation of nitriles to amines by nonclassical ruthenium hydride complexes derived from PNP pincer ligands is described. Aromatic as well as aliphatic nitriles are reduced to the corresponding primary amines. Hydrogen pressure influences the selectivity for the primary amines. The mechanism of nitrile reduction with nonclassical ruthenium hydride pincer complexes is investigated by DFT calculations. A catalytic cycle involving the coordination of nitrile trans to the pincer backbone after an initial hydride rearrangement at the ruthenium center, and the subsequent first transfer of the hydride ligand to the carbon center of the nitrile ligand is suggested as a possible reaction mechanism. Interestingly, the use of water as additive increases the selectivity for the primary amines and the rate of the reactions. Selective synthesis of primary amines by the catalytic hydrogenation of nitriles with nonclassical ruthenium hydride pincer complexes is reported. Use of water as additive increases the selectivity and rate of the reactions. Possible catalytic cycles were identified for this important reaction of industrial significance by means of DFT calculations. Copyright

Reductions of aliphatic and aromatic nitriles to primary amines with diisopropylaminoborane

Haddenham, Dustin,Pasumansky, Lubov,DeSoto, Jamie,Eagon, Scott,Singaram, Bakthan

, p. 1964 - 1970 (2009)

Diisopropylaminoborane [BH2Nf)Pr)2] in the presence of a catalytic amount of lithium borohydride (LiBH4) reduces a large variety of aliphatic and aromatic nitriles in excellent yields. BH 2NOPr)2 can be prepared by two methods: first by reacting diisopropylamineborane [(iPr)2N)BH3] with 1.1 equiv of n-butylhthium (n-BuLi) followed by methyl iodide (MeI), or reacting iPrN:BH 3 with 1 equiv of n-BuLi followed by trimethylsilyl chloride (TMSCl). BH2N(ZPr)2 prepared with MeI was found to reduce benzonitriles to the corresponding benzylamines at ambient temperatures, whereas diisopropylaminoborane prepared with TMSCl does not reduce nitriles unless a catalytic amount of a lithium ion source, such as LiBH4 or lithium tetraphenylborate (LiBPh4), is added to the reaction. The reductions of benzonitriles with one or more electron-withdrawing groups on the aromatic ring generally occur much faster with higher yields. For example, 2,4-dichlorobenzonitrile was successfully reduced to 2,4-dichlorobenzylamine in 99% yield after 5 h at 25 °C. On the other hand, benzonitriles containing electron-donating groups on the aromatic ring require refluxing in tetrahydrofuran (THF) for complete reduction. For instance, 4- methoxybenzonitrile was successfully reduced to 4-methoxybenzylamine in 80% yield. Aliphatic nitriles can also be reduced by the BH2N(iPr) 2/cat. LiBH4 reducing system. Benzyl cyanide was reduced to phenethylamine in 83% yield. BH2NOPr)2 can also reduce nitriles in the presence of unconjugated alkenes and alkynes such as the reduction of 2-hexynenitrile to hex-5-yn-l-amine in 80% yield. Unfortunately, selective reduction of a nitrile in the presence of an aldehyde is not possible as aldehydes are reduced along with the nitrile. However, selective reduction of the nitrile group at 25 °C in the presence of an ester is possible as long as the nitrile group is activated by an electron-withdrawing substituent. It should be pointed out that lithium aminoborohydrides (LABs) do not reduce nitriles under ambient conditions and behave as bases with aliphatic nitriles as well as nitriles containing acidic a-protons. Consequently, both LABs and BH2NOPr)2 are complementary to each other and offer methods for the selective reductions of multifunctional compounds.


, p. 431 (1957)

Reduction of aromatic nitriles into aldehydes using calcium hypophosphite and a nickel precursor

Mouselmani, Rim,Hachem, Ali,Alaaeddine, Ali,Métay, Estelle,Lemaire, Marc

, p. 6600 - 6605 (2018)

Herein we report the reduction of aromatic nitriles into aldehydes with calcium hypophosphite in the presence of base and nickel(ii) complex in a water/ethanol mixture. This catalytic system reduced efficiently a series of aromatic nitriles bearing different functional groups such as -Cl, -CF3, -Br, -CH3, -OCH3, -COOCH2CH3, -OH and -CHO. The corresponding aldehydes were isolated in moderate to excellent yields (30-94%).

Efficient Base-Free Hydrogenation of Amides to Alcohols and Amines Catalyzed by Well-Defined Pincer Imidazolyl-Ruthenium Complexes

Cabrero-Antonino, Jose R.,Alberico, Elisabetta,Drexler, Hans-Joachim,Baumann, Wolfgang,Junge, Kathrin,Junge, Henrik,Beller, Matthias

, p. 47 - 54 (2016)

Novel homogeneous ruthenium catalysts bearing an imidazolylaminophosphino pincer ligand have been synthesized. The active catalyst allows for the hydrogenation of a range of amides under base-free conditions to afford the corresponding alcohols and amines in high yields.

Catalytic Activity of Polynuclear Platinum Carbonyl Anions in Homogeneous Hydrogenation Reactions

Bhaduri, Sumit,Sharma, Krishna R.

, p. 727 - 732 (1982)

The homogeneous hydrogenation of benzaldehyde, heptanal, cyclohexanone, cyclohexene, acetonitrile, and benzonitrile has been studied using n4>2 (1) as the catalyst over a range of temperature (40-80 deg C) and pressure (20-64 lbf in-2).Infrared spectroscopic studies suggest the formation of a common intermediate in reactions carried out at >=60 deg C.Benzaldehyde is the most readily hydrogenated; the nature of the products depends on the pressure of hydrogen used and is selective to either benzyl alcohol or a mixture of benzene and methanol.Kinetic studies on the rate of benzyl alcohol formation indicate a first-order dependence of the rate on the concentration of (1).While the rate shows a Michaelis-Menten type of dependence on the PhCHO concentration, it seems to be independent of H2 pressure in the range 20-25 lbf in-2.Under these conditions, a value of 63.81 kJ mol-1 for the activation energy is obtained from the Arrhenius plot.A tentative mechanism for PhCHO hydrogenation is discussed.

Impregnated ruthenium on magnetite as a recyclable catalyst for the N-alkylation of amines, sulfonamides, sulfinamides, and nitroarenes using alcohols as electrophiles by a hydrogen autotransfer process

Cano, Rafael,Ramon, Diego J.,Yus, Miguel

, p. 5547 - 5557 (2011)

Various impregnated metallic salts on magnetite have been prepared, including cobalt, nickel, copper, ruthenium, and palladium salts, as well as a bimetallic palladium - copper derivative. Impregnated ruthenium catalyst is a versatile, inexpensive, and simple system for the selective N-monoalkylation of amino derivatives with poor nucleophilic character, such as aromatic and heteroaromatic amines, sulfonamides, sulfinamides, and nitroarenes, using in all cases alcohols as the initial source of the electrophile, through a hydrogen autotransfer process. In the case of sulfinamides, this is the first time that these amino compounds have been alkylated following this strategy, allowing the use of chiral sulfinamides and secondary alcohols to give the alkylated compound with a diastereomeric ratio of 92:8. In these cases, after alkylation, a simple acid deprotection gave the expected primary amines in good yields. The ruthenium catalyst is quite sensitive, and small modifications of the reaction medium can change the final product. The alkylation o amines using potassium hydroxide renders the N-monoalkylated amines, and the same protocol using sodium hydroxide yields the related imines. The catalyst can be easily removed by a simple magnet and can be reused up to ten times, showing the same activity.

A novel, chemoselective and efficient production of amines from azides using ZrCl4/NaBH4

Purushothama Chary,Raja Ram,Salahuddin,Iyengar

, p. 3559 - 3563 (2000)

A practical and cheaper reagent system ZrCl4/NaBH4 is used for the production of amines from azides is described.

Reaction of InCl3 with various reducing agents: InCl 3-NaBH4-mediated reduction of aromatic and aliphatic nitriles to primary amines

Saavedra, Jaime Z.,Resendez, Angel,Rovira, Alexander,Eagon, Scott,Haddenham, Dustin,Singaram, Bakthan

, p. 221 - 228 (2012)

While alternative methods of preparing dichloroindium hydride (HInCl 2) via the in situ reduction of InCl3 using lithium amino borohydride (LAB) were explored, generation of HInCl2 from the reduction of InCl3 by sodium borohydride (NaBH4) was also re-evaluated for comparison. The reductive capability of the InCl 3/NaBH4 system was found to be highly dependent on the solvent used. Investigation by 11B NMR spectroscopic analyses indicated that the reaction of InCl3 with NaBH4 in THF generates HInCl2 along with borane-tetrahydrofuran (BH 3?THF) in situ. Nitriles underwent reduction to primary amines under optimized conditions at 25 °C using 1 equiv of anhydrous InCl 3 with 3 equiv of NaBH4 in THF. A variety of aromatic, heteroaromatic, and aliphatic nitriles were reduced to their corresponding primary amine in 70-99% isolated yields. Alkyl halide and nitrile functional groups were reduced in tandem by utilizing the reductive capabilities of both HInCl2 and BH3?THF in a one-pot reaction. Finally, the selective reduction of the carbon bromine bond in the presence of nitriles was achieved by generating HInCl2 via the reduction InCl3 with NaBH4 in CH3CN or with lithium dimethylaminoborohydride (MeLAB) in THF.

Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Cobalt Pincer Complex

Mukherjee, Arup,Srimani, Dipankar,Chakraborty, Subrata,Ben-David, Yehoshoa,Milstein, David

, p. 8888 - 8891 (2015)

The catalytic hydrogenation of nitriles to primary amines represents an atom-efficient and environmentally benign reduction methodology in organic chemistry. This has been accomplished in recent years mainly with precious-metal-based catalysts, with a single exception. Here we report the first homogeneous Co-catalyzed hydrogenation of nitriles to primary amines. Several (hetero)aromatic, benzylic, and aliphatic nitriles undergo hydrogenation to the corresponding primary amines in good to excellent yields under the reaction conditions.


Suzuki, Hitomi,Takaoka, Koji

, p. 1733 - 1736 (1984)

By treatment with sodium hydrogentelluride in ethanol/ether at room temperature, alkyl and aryl azides are easily converted to the corresponding primary amines in good yields.

Pd/C(en) catalyzed chemoselective hydrogenation in the presence of aryl nitriles

Maegawa, Tomohiro,Fujita, Yuki,Sakurai, Ai,Akashi, Akira,Sato, Mutsumi,Oono, Keiji,Sajiki, Hironao

, p. 837 - 839 (2007)

Aromatic nitriles are not only important components of natural products, pharmaceuticals, herbicides and agrochemicals but also a synthetic equivalent of various functionalities. The development of synthetic methods of aromatic nitriles have been increasing in terms of its usefulness. Since aromatic nitriles are susceptible to the hydrogenation, it has been desired for the development of chemoselective hydrogenation method with retention of nitrile groups. Pd/C is one of the most popular catalysts for hydrogenation and many of reducible functional groups such as multiple bonds, benzyl ethers, N-Cbzs, nitro groups and so on could be easily reduced under the conditions. Therefore, it is very difficult to achieve the chemoselective hydrogenation of substrates containing two or more reducible functional groups. We have found that a Pd/C catalyst formed an isolable complex with ethylenediamine (en) employed as catalytic poison, and the complex [Pd/C(en)] catalyzed chemoselective hydrogenation of a variety of reducible functionalities distinguishing O-benzyl, N-Cbz and O-TBDMS protective groups, benzyl alcohols and epoxides. In the course of these investigations, we found the aryl nitriles could survive under the Pd/C(en)-catalyzed hydrogenation conditions in THF whose choice is important for the effective suppression. This methodology could be applied to the selective hydrogenation of alkene and alkyne functionalities in the presence of aromatic nitrile.

A convenient method for the reduction of oxime ethers to the corresponding amines


, p. 2897 - 2898 (1978)



, p. 342,346 (1954)

Versatile Dynamic Covalent Assemblies for Probing π-Stacking and Chirality Induction from Homotopic Faces

Ye, Hebo,Hai, Yu,Ren, Yulong,You, Lei

, p. 3804 - 3809 (2017)

Herein we report for the first time the use of dynamic covalent reactions (DCRs) for building a π-stacking model system and further quantifying its substituent effects (SEs), which remain a topic of debate despite the rich history of stacking. A general DCR between 10-methylacridinium ion and primary amines was discovered, in which π-stacking played a stabilizing role. Facile quantification of SEs with in situ competing π-stacking systems was next achieved in the form of amine exchange exhibiting structural diversity by simply varying components. The linear correlation with σm in Hammett plots indicates the dominance of purely electrostatic SEs, and the additivity of SEs is in line with the direct interaction model. With α-chiral amines π-stacking within the adduct enabled chirality transfer from homotopic faces. The strategy of dynamic covalent assembly should be appealing to future research of probing weak interactions and manipulating chirality.

Dimethylethylamine-Alane and N-Methylpyrrolidine-Alane. A Convenient Synthesis of Alane, a Useful Selective Reducing Agent in Organic Synthesis

Marlett, Everett M.,Park, Won Suh

, p. 2968 - 2969 (1990)



Hine,J. et al.

, p. 340 - 344 (1970)


An Efficient Ruthenium Catalyst Bearing Tetradentate Ligand for Hydrogenations of Carbon Dioxide

Zhang, Feng-Hua,Liu, Chong,Li, Wei,Tian, Gui-Long,Xie, Jian-Hua,Zhou, Qi-Lin

, p. 1000 - 1002 (2018)

A ruthenium complex with a tetradentate bipyridine ligand was proved to be a highly efficient catalyst for the conversions of CO2. Turnover numbers up to 300 000, 9800, and 2100 were achieved for the hydrogenations of CO2 to formamides, formamides to methanol and amines, and the direct hydrogenation of CO2 to methanol, respectively.

Nitrile hydrogenation using nickel nanocatalysts in ionic liquids

Konnerth, Hannelore,Prechtl, Martin H. G.

, p. 9594 - 9597 (2017)

Ni nanoparticles (NPs) embedded in imidazolium based ionic liquids (ILs) have been proven to be versatile catalysts for the selective hydrogenation of benzonitrile to benzylamine with good recyclability in a biphasic system. Influence of the used ILs and reaction conditions has been examined in detail and a wider substrate scope has been studied using benzonitrile derivatives and aliphatic nitriles.

Magnesium-Catalyzed Proficient Reduction of Oximes to Amines Using Ammonium Formate

Abiraj,Gowda, D. Channe

, p. 599 - 605 (2004)

Various aldoximes and ketoximes were selectively reduced to the corresponding amines by catalytic transfer hydrogenation employing low cost magnesium powder and ammonium formate at room temperature. Many other functionalities such as halogens, -OH, -OCH3, -COOH and -CH 3 remained unaffected. The hydrogenation is fast, mild, clean, cost effective and high yielding.

Reduction of azides to amines or amides with zinc and ammonium chloride as reducing agent

Lin, Wenqing,Zhang, Xiaomei,He, Ze,Jin, Yi,Gong, Liuzhu,Mi, Aiqiao

, p. 3279 - 3284 (2002)

Alkyl azides and acyl azides were reduced to the corresponding amines and amides with zinc and ammonium chloride as reducing agent under mild conditions in good to excellent yield.

2-(4-Nitrophenyl)-1H-indolyl-3-methyl Chromophore: A Versatile Photocage that Responds to Visible-light One-photon and Near-infrared-light Two-photon Excitations

Abe, Manabu,Guo, Runzhao,Hamao, Kozue,Lin, Qianghua,Takagi, Ryukichi

supporting information, p. 153 - 156 (2022/02/14)

Due to cell damage caused by UV light, photoremovable protecting groups (PPGs) that are removed using visible or near-infrared light are attracting attention. A 2-(4-nitrophenyl)- 1H-indolyl-3-methyl chromophore (NPIM) was synthesized as a novel PPG. Various compounds were caged using this PPG and uncaged using visible or near-infrared light. Low cytotoxicity of NPIM indicates that it may be applied in physiological studies.

Tandem Fe/Zn or Fe/In Catalysis for the Selective Synthesis of Primary and Secondary Amines?via Selective Reduction of Primary Amides

Darcel, Christophe,Wu, Jiajun

, (2022/03/18)

Tandem iron/zinc or iron/indium-catalysed reductions of various primary amides to amines under hydrosilylation conditions are reported under visible light activation. By a simple modification of the nature of the co-catalyst (Zn(OTf)2 vs In(OTf)3), Fe(CO)4(IMes) can promote the highly chemoselective reduction of primary amides into primary amines (21 examples, up to 93 % isolated yields) and secondary amines (8 examples, up to 51 % isolated yields), respectively. Notably, both benzamide and alkanamide derivatives can be reduced.

Device and production method for continuously generating 2-chloro-5-trifluoromethylpyridine


Paragraph 0018, (2021/03/11)

The invention relates to a device for continuously generating 2-chloro-5-trifluoromethylpyridine. The invention also discloses a production method for continuously generating 2-chloro-5-trifluoromethylpyridine. Benzyl chloride is used as a raw material, a

Indirect reduction of CO2and recycling of polymers by manganese-catalyzed transfer hydrogenation of amides, carbamates, urea derivatives, and polyurethanes

Liu, Xin,Werner, Thomas

, p. 10590 - 10597 (2021/08/20)

The reduction of polar bonds, in particular carbonyl groups, is of fundamental importance in organic chemistry and biology. Herein, we report a manganese pincer complex as a versatile catalyst for the transfer hydrogenation of amides, carbamates, urea derivatives, and even polyurethanes leading to the corresponding alcohols, amines, and methanol as products. Since these compound classes can be prepared using CO2as a C1 building block the reported reaction represents an approach to the indirect reduction of CO2. Notably, these are the first examples on the reduction of carbamates and urea derivatives as well as on the C-N bond cleavage in amides by transfer hydrogenation. The general applicability of this methodology is highlighted by the successful reduction of 12 urea derivatives, 26 carbamates and 11 amides. The corresponding amines, alcohols and methanol were obtained in good to excellent yields up to 97%. Furthermore, polyurethanes were successfully converted which represents a viable strategy towards a circular economy. Based on control experiments and the observed intermediates a feasible mechanism is proposed.

Generation of Oxidoreductases with Dual Alcohol Dehydrogenase and Amine Dehydrogenase Activity

Tseliou, Vasilis,Schilder, Don,Masman, Marcelo F.,Knaus, Tanja,Mutti, Francesco G.

supporting information, p. 3315 - 3325 (2020/12/11)

The l-lysine-?-dehydrogenase (LysEDH) from Geobacillus stearothermophilus naturally catalyzes the oxidative deamination of the ?-amino group of l-lysine. We previously engineered this enzyme to create amine dehydrogenase (AmDH) variants that possess a new hydrophobic cavity in their active site such that aromatic ketones can bind and be converted into α-chiral amines with excellent enantioselectivity. We also recently observed that LysEDH was capable of reducing aromatic aldehydes into primary alcohols. Herein, we harnessed the promiscuous alcohol dehydrogenase (ADH) activity of LysEDH to create new variants that exhibited enhanced catalytic activity for the reduction of substituted benzaldehydes and arylaliphatic aldehydes to primary alcohols. Notably, these novel engineered dehydrogenases also catalyzed the reductive amination of a variety of aldehydes and ketones with excellent enantioselectivity, thus exhibiting a dual AmDH/ADH activity. We envisioned that the catalytic bi-functionality of these enzymes could be applied for the direct conversion of alcohols into amines. As a proof-of-principle, we performed an unprecedented one-pot “hydrogen-borrowing” cascade to convert benzyl alcohol to benzylamine using a single enzyme. Conducting the same biocatalytic cascade in the presence of cofactor recycling enzymes (i.e., NADH-oxidase and formate dehydrogenase) increased the reaction yields. In summary, this work provides the first examples of enzymes showing “alcohol aminase” activity.

Process route upstream and downstream products

Process route

4-methoxy-benzoic acid-(1-ethoxy-3-benzylimino-but-1-enyl ester)

4-methoxy-benzoic acid-(1-ethoxy-3-benzylimino-but-1-enyl ester)

4-methoxybenzoic acid

4-methoxybenzoic acid



Conditions Yield
benzyl bromide

benzyl bromide



Conditions Yield
With 5-methyl-1,3,4-thiadiazol-2-amine; triethylamine; In ethanol; water; at 25 ℃; for 1h;
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / Inert atmosphere
1.2: 8 h / Inert atmosphere
1.3: 2 h / 60 °C / Inert atmosphere
2.1: titanium(III) chloride; water / tetrahydrofuran / pH 10 / Reflux; Alkaline aq. solution; Inert atmosphere
With n-butyllithium; titanium(III) chloride; water; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C
2: hydrogenchloride / water / 3 h / 100 °C
With hydrogenchloride; potassium carbonate; In water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1.1: potassium carbonate / 1 h / Milling
1.2: 1 h / Milling
2.1: ethylenediamine / neat (no solvent) / Milling
With potassium carbonate; ethylenediamine; In neat (no solvent);


4-fluorobenzylic alcohol

4-fluorobenzylic alcohol









Conditions Yield
With ammonia; hydrogen; Ni/C catalyst; In water; at 120 ℃; for 17.5h; under 28502.9 - 33753.4 Torr;




Conditions Yield
With sodium ethanolate; In methanol; at 80 ℃; for 2h;
With sodiumsulfide nonahydrate; In water; at 100 ℃; for 12h;
Multi-step reaction with 2 steps
1: 3 h / Reflux
2: triphenylphosphine; triethylamine / dichloromethane; tetrachloromethane / 4 h / Reflux; Inert atmosphere
With triethylamine; triphenylphosphine; In tetrachloromethane; dichloromethane;
benzyl azide

benzyl azide



Conditions Yield
With Zn(BH4)2(Ph3P)2; In tetrahydrofuran; for 0.25h; Heating;
With sodium tetrahydroborate; tin bis(1,2-benzenedithiolate); In tetrahydrofuran; phosphate buffer; at 10 ℃; for 0.5h; pH=10; Further Variations:; pH-values; Solvents; Product distribution;
With (Sn(SPh)3)(Et3N); In benzene; at 15 ℃; for 0.0833333h;
With iron(III)-acetylacetonate; hydrazine hydrate; In methanol; at 150 ℃; for 0.05h; chemoselective reaction; Microwave irradiation;
With hydrazine hydrate; In ethanol; at 20 ℃; chemoselective reaction;
With ammonium chloride; indium; In ethanol; for 1h; Heating;
With aluminum oxide; potassium hydroxide; hydrazine; In neat (no solvent); for 1h; Milling;
With 10% palladium on activated charcoal; hydrogen; for 2.5h;
With tin(ll) chloride; In methanol; for 0.5h; Ambient temperature;
With sodium tetrahydroborate; zirconium(IV) chloride; In tetrahydrofuran; at 0 - 35 ℃; for 0.333333h;
With 5%-palladium/activated carbon; hydrogen; ammonium formate; In methanol; under 2068.65 Torr; Flow reactor;
With hydrogen; In ethanol; at 20 ℃; for 2h; under 760.051 Torr;
With triphenylphosphine; In tetrahydrofuran; hexane; water;
With triphenylphosphine-2-carboxamide; In tetrahydrofuran; water; at 20 ℃; for 2h;
With sodium sulfide; water; for 0.5h; Reflux;
With boron tribromide; In dichloromethane; at 0 - 35 ℃; for 12h; Inert atmosphere;
With 1-phenylphospholane-1-oxide; 1,3-diphenyl-disiloxane; In tetrahydrofuran; at 23 ℃; for 24h; Reagent/catalyst; Solvent;
With ammonia; iron(II) sulfate; In methanol; water; at 20 ℃; for 3h;
With samarium diiodide; In tetrahydrofuran; for 0.333333h; Ambient temperature;
With samarium diiodide; In tetrahydrofuran; for 0.333333h; Product distribution; Ambient temperature; reductions of alkyl-, aryl- and aroyl azides;
benzyl azide; With hydrazine hydrate; for 0.166667h; Inert atmosphere;
for 10h; chemoselective reaction; Irradiation;
With ammonium chloride; zinc; In ethanol; water; for 0.166667h; Heating;
With hydrogen; MCM-silylamine Pd(II); In methanol; at 20 ℃; for 0.5h;
With lithium dimethylamino borohydride; In tetrahydrofuran; at 25 ℃; for 2h;
With n-butyllithium; dimethylamine borane; In tetrahydrofuran; at 0 ℃;
With hydrogenchloride; indium; In tetrahydrofuran; at 20 ℃; for 2h;
With iron(III) chloride; sodium iodide; In acetonitrile; at 20 ℃; for 0.333333h;
With methanol; sodium tetrahydroborate; In tetrahydrofuran; for 2h; Heating;
With hydrogen; In ethanol; at 20 ℃; for 6h; under 760.051 Torr; Schlenk technique;
With sodium hydrogen telluride; In diethyl ether; ethanol; for 0.25h; Ambient temperature;
With ammonium formate; zinc; In methanol; at 20 ℃; for 0.416667h;
With iron; In water; at 20 ℃; for 4h; Inert atmosphere;
benzyl azide; With 9-phenyl-9-phosphafluorene; phenylsilane; In 1,4-dioxane; at 101 ℃; for 16h; Inert atmosphere;
With water; In 1,4-dioxane; at 20 ℃; Inert atmosphere;
With zinc(II) tetrahydroborate; silica gel; In 1,2-dimethoxyethane; for 8h; Ambient temperature;
With iron(III) chloride; N,N-Dimethylhydrazine; In methanol; for 2.5h; Ambient temperature;
With hexacarbonyl molybdenum; In ethanol; for 1.5h; Heating;
With trifluoroacetic acid; copper; In water; acetonitrile; at 60 ℃; for 4.5h;
With triphenylphosphine; In tetrahydrofuran; water; at 20 ℃;
With C24H21CuN3O3; sodium L-ascorbate; In water; tert-butyl alcohol; at 80 ℃; for 6h; Inert atmosphere;
With trisodium arsenite; ethanol;
With 2-Sulfanylpyridine; tin(II) iodide; triethylamine; In acetonitrile; for 2h;
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate; In tetrahydrofuran; for 11h; Heating;
100 % Chromat.
With (Sn(SPh)3)(Et3N); In benzene; at 15 ℃; for 0.0833333h; Product distribution; Rate constant; other reagents;
With Amberlite IRA-400; borohydride form; copper(II) sulfate; In methanol; at 20 ℃; for 6h;
99 % Chromat.
With methyltriphenylphosphonium tetrahydroborate; In dichloromethane; for 1h;
90 % Chromat.
With methanol; sodium sulfide;
With hydrogenchloride; dichloroborane-dimethyl sulfide; Yield given. Multistep reaction; 1) CH2Cl2, RT then 1 h, reflux, 2) 80 deg C, 40 min;
With trisodium thiophosphate; In water; isopropyl alcohol; for 3h; Reflux;
Multi-step reaction with 2 steps
1: 1,4-dioxane-d8 / 0.5 h / 101 °C / Inert atmosphere
2: phenylsilane; water / 1,4-dioxane-d8 / 2.67 h / 101 °C / Inert atmosphere
With phenylsilane; water; In 1,4-dioxane-d8;
With hydrogen; palladium; In tetrahydrofuran; N,N-dimethyl-formamide; at 50 ℃; for 21.5h; under 6080.41 Torr; Solvent; Inert atmosphere;
With triphenylphosphine; In tetrahydrofuran-d8; water-d2; for 15h;
98 %Spectr.
With formic acid; 2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 30h; Irradiation;
89 %Chromat.








Conditions Yield
With hydrogen; at 180 ℃; Temperature; Flow reactor;
With hydrogen; cobalt; palladium; In ethanol; under 760 Torr; Title compound not separated from byproducts; Ambient temperature;
With Ni/Al2O3; carbon dioxide; hydrogen; In water; at 80 ℃; for 6.5h; under 75007.5 Torr; Autoclave;
51.2 %Chromat.
37 %Chromat.
9.8 %Chromat.
With platinum; hydrogen; acetic acid; In ethanol; at 40 ℃; for 24h; under 750.075 Torr; Solvent; Schlenk technique; Sealed tube;
85.8 %Chromat.
7.6 %Chromat.
5.4 %Chromat.




Conditions Yield
With ammonia; hydrogen; In methanol; at 90 ℃; for 4h; under 15001.5 Torr; Solvent; Temperature; Pressure; Autoclave;
With Candida boidinii formate dehydrogenase; Geobacillus stearothermophilus ε‐deaminating L‐lysine dehydrogenase variant 1; nicotinamide adenine dinucleotide; In aq. buffer; at 30 ℃; for 24h; pH=8.5; Reagent/catalyst; Enzymatic reaction;
With ammonium hydroxide; hydrogen; In ethanol; at 130 ℃; for 12h; under 7500.75 Torr; Autoclave;
With ammonia; hydrogen; In methanol; at 30 ℃; for 15h; Autoclave;
benzaldehyde; With aluminium(III) triflate; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 1,2-bis-(diphenylphosphino)ethane; In dodecane; toluene; at -5 ℃; for 0.5h; under 3000.3 Torr; Autoclave;
With hydrogen; In dodecane; toluene; at 120 ℃; for 16h; under 30003 Torr; chemoselective reaction; Acidic conditions;
With C24H22N4*BF4(1-)*Ru(2+)*Cl(1-)*C10H14; ammonium formate;
With N,N'-bis(salicylidene)-1,2-phenylene-diaminocobalt(II); ammonia; hydrogen; In tetrahydrofuran; water; at 120 ℃; for 24h; Autoclave;
With ammonium formate; In toluene; at 80 ℃; for 3h; chemoselective reaction; Inert atmosphere;
With ammonium formate; In toluene; at 80 ℃; for 3h; chemoselective reaction; Inert atmosphere;
With ammonia; hydrogen; In methanol; at 89.84 ℃; for 6h; under 30003 Torr;
With ammonia; hydrogen; In methanol; at 90 ℃; for 5h; under 15001.5 Torr;
benzaldehyde; With palladium diacetate; 2-amino-phenol; trifluoroacetic acid; In 1,2-dichloro-ethane; for 10h;
With phenylacetylene; In 1,2-dichloro-ethane; at 80 ℃;
With (S)-1-phenyl-ethylamine; pyridoxal 5'-phosphate; pQR1108; In aq. phosphate buffer; dimethyl sulfoxide; at 30 ℃; for 18h; pH=8; Enzymatic reaction;
With sodium tetrahydroborate; ammonia; acetic acid; at 20 ℃; for 2h;
With ammonium hydroxide; hydrogen; In water; at 99.84 ℃; for 2h; under 1900.13 Torr; Autoclave;
Multi-step reaction with 2 steps
1: water; NH2Cl / 0 °C
2: sodium-amalgam; acetic acid
With sodium amalgam; chloroamine; water; acetic acid;
Multi-step reaction with 2 steps
1: hydrazine
2: aluminium amalgam
With aluminium amalgam; hydrazine;
Multi-step reaction with 6 steps
1.1: methanol / 5 h / 20 °C
2.1: sodium tetrahydroborate / methanol / 0.67 h / 20 °C
3.1: dichloromethane / 5 h / 20 °C
4.1: acetonitrile / 0.5 h / 20 °C
5.1: lithium trifluoromethanesulfonate / N,N-dimethyl-formamide / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere
5.2: 0 °C / Inert atmosphere
5.3: 0 - 20 °C / Inert atmosphere
6.1: water; acetic acid / acetonitrile / 17 h / 80 °C
6.2: 17 h / 70 °C
With sodium tetrahydroborate; water; lithium trifluoromethanesulfonate; acetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride
2: sodium tetrahydroborate; nickel; sodium hydroxide / methanol; water / 20 - 30 °C
With sodium tetrahydroborate; hydroxylamine hydrochloride; nickel; sodium hydroxide; In methanol; water;
Multi-step reaction with 2 steps
1: ammonia; hydrogen / water / Green chemistry
2: hydrogen
With ammonia; hydrogen; In water;
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; sodium carbonate / ethanol / 20 °C
2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
With palladium 10% on activated carbon; hydroxylamine hydrochloride; hydrogen; sodium carbonate; In ethanol;
With NADH; In aq. buffer; at 25 ℃; pH=9.6; Kinetics;
Multi-step reaction with 2 steps
1.1: hydroxylamine hydrochloride / ethanol / 0.58 h / 20 °C
2.1: hydrogenchloride; zinc / ethanol; water / 0.25 h / 20 °C
2.2: 0.25 h / 20 °C
With hydrogenchloride; hydroxylamine hydrochloride; zinc; In ethanol; water;
With L-alanin; pyridoxal 5'-phosphate; Chromobacterium violaceum ω-transaminase; E. coli acetohydroxyacid synthase I; thiamine pyrophosphate; 2-oxo-propionic acid; flavin adenine dinucleotide; magnesium chloride; In aq. buffer; pH=7.5; Enzymatic reaction;
With glucose dehydrogenase; D-Alanine; ω-transaminase; ATA117; lactate dehydrogenase; catalase from bovine liver; Enzymatic reaction;
With glucose dehydrogenase; L-alanin; D-glucose; L-alanine dehydrogenase; amine transaminase; ammonium chloride; NADH; sodium hydroxide; In dimethyl sulfoxide; at 37 ℃; for 22h; pH=8.2; Darkness; Enzymatic reaction;
Multi-step reaction with 2 steps
1: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere
2: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 94 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
With glucose dehydrogenase; L-alanin; D-glucose; L-alanine dehydrogenase; amine transaminase; ammonium chloride; NADH; rac-Pro-OH; sodium hydroxide; In dimethyl sulfoxide; 1: |Aldol Addition;
With (S)-1-phenyl-ethylamine; Halomonas elongata ω-transaminase; In aq. phosphate buffer; at 37 ℃; pH=8; Enzymatic reaction;
With glucose dehydrogenase; D-Glucose; L-alanin; L-alanine dehydrogenase; chromobacterium violaceum amine transaminase; ammonium chloride; NADH; In dimethyl sulfoxide; at 37 ℃; for 23h; pH=8.2; Solvent; Reagent/catalyst; Darkness; Enzymatic reaction;
Multi-step reaction with 2 steps
1.1: hydroxylamine hydrochloride; pyridine / ethanol / 22 h / 70 °C
2.1: hydrogenchloride / ethanol; water / 0.25 h / 20 °C
2.2: 1 h / Reflux
2.3: Amberlyst A-21
With pyridine; hydrogenchloride; hydroxylamine hydrochloride; In ethanol; water;
With ammonium hydroxide; nickel-aluminum alloy; water; at 20 ℃; for 2h; Sonication; Green chemistry;
92 %Chromat.
With L-alanin; pyridoxal 5'-phosphate; halomonas elongata transaminase Y149F mutant; In aq. phosphate buffer; dimethyl sulfoxide; at 37 ℃; for 24h; pH=8; Reagent/catalyst; Enzymatic reaction;
Multi-step reaction with 2 steps
1: pyridine; hydroxylamine hydrochloride / ethanol / Reflux
2: hydrogenchloride; zinc / ethanol; water / 1 h / 0 - 90 °C
With pyridine; hydrogenchloride; hydroxylamine hydrochloride; zinc; In ethanol; water;
With ammonium hydroxide; hydrogen; In ethanol; at 95 ℃; for 6h; under 9000.9 Torr; Autoclave; Green chemistry;
With ammonia; hydrogen; In tert-butyl alcohol; at 120 ℃; for 15h;
87 %Chromat.
With ammonium hydroxide; hydrogen; In isopropyl alcohol; at 120 ℃; for 15h; under 22502.3 Torr; Autoclave;
62 %Chromat.
With transaminase; 1,2-benzenedimethanamine; pyridoxal 5'-phosphate; In aq. phosphate buffer; at 30 ℃; for 48h; pH=7.5; pH-value; Reagent/catalyst; Solvent; Temperature; Catalytic behavior; Enzymatic reaction;
With ruthenium; ammonia; hydrogen; In methanol; at 89.84 ℃; for 4h; under 15001.5 Torr; Reagent/catalyst; Catalytic behavior;
95 %Chromat.
Multi-step reaction with 2 steps
1: formic acid / 0.08 h / 180 °C / 7500.75 Torr / Microwave irradiation; Inert atmosphere
2: sodium ethanolate / methanol / 2 h / 80 °C
With formic acid; sodium ethanolate; In methanol;
With ammonium hydroxide; hydrogen; In methanol; for 12h; under 750.075 Torr; Autoclave; Heating;
99.1 %Chromat.
With ammonia; hydrogen; In tert-butyl alcohol; at 120 ℃; for 24h; Autoclave; High pressure;
88 %Chromat.
With Candida boidinii formate dehydrogenase; F173A-mutated wild-type Geobacillus stearothermophilus ε-deaminating L-lysine dehydrogenase; NAD; ammonia; ammonium formate; In aq. buffer; at 50 ℃; for 48h; pH=7.8; Temperature; Enzymatic reaction;
With nickel(II) tetrafluoroborate hexahydrate; ammonia; hydrogen; bis(2-diphenylphosphinoethyl)phenylphosphine; In 2,2,2-trifluoroethanol; at 100 ℃; for 24h; chemoselective reaction;
97 %Chromat.
With ammonium hydroxide; hydrogen; at 130 ℃; for 20h; under 48754.9 Torr;
With ammonium formate; C23H23ClF3IrN2O; In tetrahydrofuran; at 37 ℃; for 15h; Reagent/catalyst; Solvent; chemoselective reaction; Catalytic behavior;
96 %Spectr.
benzaldehyde; With hydroxylamine hydrochloride; sodium acetate; In ethanol; at 20 ℃; for 12h;
With hydrogenchloride; zinc; In ethanol; water; at 70 ℃; for 2h;
With ammonia; hydrogen; In methanol; at 90 ℃; for 4h; under 15001.5 Torr; Reagent/catalyst; Autoclave;
97 %Spectr.
With ammonium acetate; In isopropyl alcohol; at 120 ℃; for 0.25h; Microwave irradiation;
With hydrogen; ammonium hydroxide; at 90 ℃; under 7500.75 Torr; Reagent/catalyst;
89 %Chromat.
With ammonia; hydrogen; In methanol; at 90 ℃; for 4h; under 15001.5 Torr; Autoclave; Green chemistry;




Conditions Yield
With [Ir(H)2(Cl)(HN{CH2CH2P(iPr)2}2)]; potassium tert-butylate; hydrogen; In tetrahydrofuran; at 130 ℃; for 24h; under 37503.8 Torr; Autoclave;
With sodium hydroxide; at 250 - 275 ℃;
With ammonium bromide; 3-azapentane-1,5-diamine; at 110 ℃; for 5h; Microwave irradiation;
> 95 %Spectr.
With C36H54Cl2N2P2Ru; hydrogen; sodium hydride; In toluene; at 160 ℃; for 26h; under 45004.5 - 60006 Torr; Autoclave; Sealed tube;
99 %Spectr.




Conditions Yield
With titanium(III) chloride; lithium; In tetrahydrofuran; at 20 ℃; for 1h;
With titanium(III) chloride; lithium; In tetrahydrofuran; reflux, 3 h; 25 deg C, 30 min;
57 % Chromat.




Conditions Yield
N-benzyl-3,3-dimethoxypropylsulfonamide; With p-toluenesulfonic acid monohydrate; In water; acetone; at 0 - 20 ℃; for 6h;
With sodium hydroxide; In methanol; water; acetone; at 0 - 20 ℃; for 1.08333h;

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