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Cas Database

100-47-0

100-47-0

Identification

  • Product Name:Benzonitrile

  • CAS Number: 100-47-0

  • EINECS:202-855-7

  • Molecular Weight:103.123

  • Molecular Formula: C7H5N

  • HS Code:29269090

  • Mol File:100-47-0.mol

Synonyms:Benzene,cyano-;Benzenecarbonitrile;Benzenenitrile;Benzoic acid nitrile;Benzonitril;Cyanobenzene;NSC 8039;Phenyl cyanide;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH312 Harmful in contact with skin

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. 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. Rest. Refer for medical attention . Benzonitrile may enter the human body by ingestion, absorption through the skin, or inhalation. The earliest symptoms of cyano compound intoxication may be weakness, headaches, confusion, and occasionally nausea and vomiting. The respiratory rate and depth will usually be increased at the beginning and at later stages become slow and gasping. Blood pressure is usually normal, especially in the mild or moderately severe cases, although the pulse rate is usually more rapid than normal. (USCG, 1999) 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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Cyanide and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Foam, dry chemical, carbon dioxide. Water may be ineffective. Cool exposed containers with water. Wear goggles & self-contained breathing apparatus. Special Hazards of Combustion Products: Toxic hydrogen cyanide and oxides of nitrogen may form in 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: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Remove all ignition sources. Ventilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, or a similar material adn deposit in sealed containers. it maybe nessary to contain and dispose of this chemical as a hazardous waste.

  • 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. Separated from food and feedstuffs. Well closed. Keep in a well-ventilated room.Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Hygroscopic: Handle and store under inert gas.

  • 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:TRC
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Relevant articles and documentsAll total 1393 Articles be found

Improving Robustness: In Situ Generation of a Pd(0) Catalyst for the Cyanation of Aryl Bromides

Coombs, John R.,Fraunhoffer, Kenneth J.,Simmons, Eric M.,Stevens, Jason M.,Wisniewski, Steven R.,Yu, Miao

, p. 7040 - 7044 (2017)

Conditions have been developed for the palladium-catalyzed cyanation of aryl bromides utilizing the air-stable XantPhos-PdCl2 precatalyst. By employing a trialkylamine as a reducing agent, the active Pd(0) species is generated in situ, alleviating the need to employ the air-sensitive Pd2(dba)3. Twenty-two substituted benzonitriles have been synthesized using this method.

Oxidative conversion of amines into their corresponding nitriles using o-iodoxybenzoic acid (IBX)/iodine: Selective oxidation of aminoalcohols to hydroxynitriles

Chiampanichayakul, Supanimit,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Kuhakarn, Chutima

, p. 2045 - 2048 (2008)

o-Iodoxybenzoic acid (IBX)/iodine in dimethyl sulfoxide at 65 °C oxidatively and efficiently converted various amines into the corresponding nitriles in good to excellent yields. Under the reaction conditions, amines were selectively oxidized to the nitrile in the presence of a primary hydroxy group within the same molecule. Thieme Stuttgart.

KINETICS OF REACTIONS OF O-(2,4-DINITROPHENYL) BENZALDOXIMES WITH METHYLAMINE, CYCLOHEXYLAMINE AND PIPERIDINE. REACTIVITY AT DIFFERENT ELECTROPHILIC SITES

Bhattacharjee, Gurudas,Singh, Ashok K.,Saikia, Ranjumoni

, p. 4537 - 4540 (1988)

Kinetics of reaction of E-O-(2,4-dinitrophenyl) benzaldoximes have been studied with MeNH2, cyclohexylamine (CHA) and piperdine (PiP) in 1:1 (v/v) ethanol-water at 35+/-0.1 deg C under pseudo first order conditions.The reactions are overall second order, first order with respect to each reactant.Hammett plots are linear with a ρ value of +0.75 for MeNH2, +0.61 for CHA and +1.25 for PiP.MeNH2 and CHA predominantly give the corresponding N-(2,4-dinitrophenyl)amine with attack at the aromatic carbon in sharp contrast to earlier observation with OH-.With piperidine both elimination and substitution products are obtained, the former product predominanting when strong electron-withdrawing substituents are present in the phenyl ring of the oxime.

Synthetic Reactions in Polyethylene Glycol. Diazotization and Sandmeyer Reactions of Anilines in Polyethylene Glycol-Methylene Dichloride

Suzuki, Nobutaka,Kaneko, Yoshihiro,Nomoto, Tateo,Izawa, Yasuji

, p. 1523 - 1524 (1984)

Diazotization and the Sandmeyer reactions of representative arylamines proceed smoothly in polyethylene glycol-CH2Cl2 and have been found to be effective for the preparation of aryl halides and cyanides.

Efficient synthesis of aromatic nitriles via cyanation of aryl bromides and K4[Fe(CN)6] catalyzed by a palladium(II) complex

Guo, Mengping,Ge, Junying,Zhu, Zhiyong,Wu, Xiaochun

, p. 213 - 215 (2013)

Cyanation of aryl bromides and K4[Fe(CN)6] were carried out in the presence of catalytic amounts of {[(PhCH2O) 2P(CH3)2CHNCH(CH3)2] 2PdCl2} (PdCl2L2) in DMF and a variety of Aromatic nitriles were obtained in good yields under aerobic conditions.

COMPARISON OF THE THERMAL AND MASS-SPECTROMETRIC FRAGMENTATION OF 2,4-THIOXO(OXO)DIHYDRO-5,6-BENZO-1,3-THIAZINES

Stach, I.,Herzschuh, R.,Leistner, S.,Wagner, H.

, p. 265 - 268 (1983)

The pyrolysis of a series of phenyl- and methyl-substituted 2,4-thioxo(oxo)dihydro-5,6-benzo-1,3-thiazines at the Curie point was studied.Processes involving retrodiene fragmentation with the formation of, respectively, phenyisothiocyanate or phenylisocyanate lie at the foundation of the thermal transformations of these compounds.Among other stable pyrolysis products, aniline, benzonitrile, and benzene were identified by gas chromatography and mass spectrometry.Pyrolysis directly in the mass spectrometer gives a larger number of fragmentation products, since it makes it possible to also record compounds with low stabilities.The results of the two methods of analysis correlate well with one another.

Reaction of Thioamides with Silver Carboxylates in Aprotic Media. A Nucleophilic Approach to the Synthesis of Imides, Amides, and Nitriles.

Avalos, Martin,Babiano, Reyes,Duran, Carlos J.,Jimenez, Jose L.,Palacios, Juan C.

, p. 477 - 480 (1994)

Synthesis of nitriles, imides, and amides by reaction of silver carboxylates with unsubstituted, N-substituted, and N,N-disubstituted thiomaides in aprotic media are described.

Rational catalysis design on the basis of mechanistic understanding: Highly efficient Pd-catalyzed cyanation of aryl bromides with NaCN in recyclable solvents

Ushkov, Alexander V.,Grushin, Vladimir V.

, p. 10999 - 11005 (2011)

Rational catalysis design on the basis of a detailed mechanistic understanding has been used to successfully develop the first efficient general Pd-catalyzed aromatic cyanation reaction under the highly sought after practicable conditions: (i) MCN (M = Na or K) as a cyanide source; (ii) low-boiling recyclable solvents; and (iii) minimal quantities of inexpensive, nontoxic promoters. The developed catalytic reaction converts aromatic bromides to the corresponding nitriles in 88-99% isolated yield with NaCN and 0.5-1.0 mol % of a t-Bu3P-monoligated Pd catalyst in MeCN-THF within 2 h at 70 °C. The process exhibits high functional group tolerance.

Douglas et al.

, p. 1127 (1953)

-

Hauser,Le Maistre,Rainsford

, p. 1056,1058 (1935)

-

A base-induced ring-opening process of 2-substituted-1,3,4-oxadiazoles for the generation of nitriles at room temperature

Lu, Guo-Ping,Lin, Ya-Mei

, p. 371 - 374 (2014)

A novel base-catalysed 1,3,4-oxadiazole fragmentation for the synthesis of nitriles at room temperature has been developed. This reaction is performed under transition-metal-free conditions, and provides a new ring cleavage reaction of 1,3,4-oxadiazoles in organic synthesis.

-

Kirsanow,Solotow

, (1950)

-

Effect of Zn Substitutions in YBa2Cu3O6+x Phases on Reactivity during the Ammoxidation of Toluene

Otamiri, Jonathan C.,Andersson, Arne,Andersson, S. Lars T.,Crow, Jack E.,Gao, Ye

, p. 1265 - 1271 (1991)

Zn substitution in Y-Ba-Cu-O-phases influences the catalytic ammoxidation of toluene.The activity for formation of both benzonitrile and CO2 at low and high O2 pressures, respectively, decreases strongly with increasing Zn content up to 4percent.Above this substitution level, the activity, however, increases slightly.Characterisations of the surface by XPS and of the bulk by XRD analysis, indicate the presence of overlayers on the catalysts.In these overlayers, irrespective of the Zn content of catalysts, CuI states predominate at low O2 pressure and CuII at high pressure.These states are associated with selective and non-selective properties, respectively.The activity of the catalysts shows a general tendency to increase with surface copper concentrations as found from XPS studies.However, strong deviations from linearity indicate that the activity of the overlayer is greatly influenced by the bulk acting as a support.

The Pd(0) nanoparticles stabilized by collagen fibers as a recyclable heterogeneous catalyst for the cyanation of aryl bromides using k4fe(cn)6 as non-toxic source of cyanide

Bahari, Siavash

, p. 523 - 526 (2013)

A new method for the synthesis of aryl nitriles has been developed by the cyanation of aryl bromides in the presence of the Pd(0) nanoparticles stabilized by collagen fibers as a highly active, air-stable and recyclable heterogeneous catalyst. This method has the advantages of high yields, simple methodology and easy work-up. The catalyst was recovered and reused several times without the significant loss of its catalytic performance.

Substituent effect on exo stereoselectivity in the 1,3-dipolar cycloaddition reaction of tulipalin A with nitrile ylides

Melsa, Petr,Cajan, Michal,Havlas, Zdenek,Mazal, Ctibor

, p. 3032 - 3039 (2008)

(Chemical Equation Presented) 1,3-Dipolar cycloaddition reactions of dihydro-3-methylene-2(3H)-furanone (tulipalin A) with various benzonitrile(p-X-benzylide) ylides prefer formation of exo-cycloadducts in the extent corresponding to an increasing electron donor character of the substituent X in the para-position of the benzylide phenyl ring of the 1,3-dipolar reagent. The substituent effect on diastereoselectivity of the 1,3-DC reaction is rationalized in terms of CH/π interaction between the dipole and the dipolarophile in an exo-transition state. The determining role of such an interaction is demonstrated by the correlation of the observed diastereoselectivities with substituent Hammett σ constants, which shows a small negative ρ value. A certain contribution of CO/π interaction between the lactone carbonyl and the substituted phenyl ring to mediation of the substituent effect is also discussed. The energy profiles of both reaction pathways were analyzed using DFT and RI-MP2 theoretical approaches. Calculated energy and structural differences between located transition states are consistent with reaction diastereoselectivities.

Seaweed-like 2D-2D Architecture of MoS2/rGO Composites for Enhanced Selective Aerobic Oxidative Coupling of Amines

Wang, Mingming,Wu, Haihong,Shen, Chaoren,Luo, Shuping,Wang, Dan,He, Lin,Xia, Chungu,Zhu, Gangli

, p. 1935 - 1942 (2019)

To provide a solution for pursuing high redox reactivity beyond the compromise between the numbers of sulfur vacancies and electron transfer ability, 2D-2D architecture of MoS2/rGO composite was fabricated with 2D graphene-like transition metal

The Dual Reactivity of 5-S/5-O-Phenyl-1,4,2-oxathiazoles: A Fragmentation Pathway That Affords Nitriles in the Presence of Water

Lim, Yi Wee,Hewitt, Russell J.,Burkett, Brendan A.

, p. 4840 - 4842 (2015)

The rearrangement of substituted 1,4,2-oxathiazoles to nitriles in the presence of water is described. Preliminary investigations suggest that the reaction pathway proceeds via a 1,4,2-oxathiazolium intermediate, followed by trapping with water and subsequent decomposition to products. An unprecedented rearrangement of 5-phenyl-1,4,2-oxathiazoles bearing a C5 leaving group to nitriles in the presence of water is described.

An environmentally benign system; a simple and effective procedure for dehydration of oximes into nitriles in solvent free conditions

Hekmatshoar, Rahim,Sajadi, Sodeh,Heravi, Majid M.

, p. 5 - 7 (2008)

In an environmentally benign solvent free system aldoximes are rapidly transformed into nitriles using trimethylsilylchloride under mild conditions.

-

Binkley

, p. 1893 (1969)

-

Heterogeneously catalyzed synthesis of primary amides directly from primary alcohols and aqueous ammonia

Yamaguchi, Kazuya,Kobayashi, Hiroaki,Oishi, Takamichi,Mizuno, Noritaka

, p. 544 - 547 (2012)

In the presence of a manganese oxide based octahedral molecular sieve (OMS-2), a range of primary amides could be synthesized directly from primary alcohols and ammonia (see scheme). The observed catalysis was heterogeneous, and the recovered catalyst could be reused many times without an appreciable loss of its catalytic performance. Copyright

-

Mukaiyama,T.,Hata,T.

, p. 1712 - 1715 (1960)

-

Catalytic C-C bond cleavage and C-Si bond formation in the reaction of RCN with Et3SiH promoted by an iron complex

Nakazawa, Hiroshi,Kamata, Kouji,Itazaki, Masumi

, p. 4004 - 4006 (2005)

Catalytic C-C bond cleavage of acetonitrile and C-Si bond formation have been attained in the photoreaction of MeCN with Et3SiH in the presence of an iron complex, Cp(CO)2FeMe. This catalytic system can be applied for arylnitrile C-C

A new method for the generation of nitriles from aldoximes

Jose, Binoy,Sulatha,Madhavan Pillai,Prathapan, Sreedharan

, p. 1509 - 1514 (2000)

A mild and efficient method for the stereoselective dehydration of α-aldoximes to the corresponding nitriles is described which utilises methyl (carboxysulfamoyl)triethylammonium hydroxide inner salt (Burgess reagent) as the dehydrating agent.

-

van Tamelen,Rudler

, p. 5253 (1970)

-

The facile fragmentation of trifluoroacetyl groups to nitriles

Kende, Andrew S.

, p. 4035 - 4038 (1995)

Trifluoroacetyl groups attached to a carbon atom devoid of hydrogen undergo facile, high-yield conversion to nitriles by reaction with MeAlClNH2, followed by KOtBu, in a 'one-pot' reaction sequence.

Reduction of aryl mesylates catalyzed by nickel complexes

Sasaki, Ken,Kubo, Tatsuya,Sakai, Mutsuji,Kuroda, Yasuhisa

, p. 617 - 618 (1997)

Aryl mesylates were found to be deoxygenatively reduced into the corresponding aromatic hydrocarbons by using nickel(0)-dppb/PPh3 catalyst with zinc powder and an alcohol as a hydrogen donor.

Ultrasound enhanced PTC conversion of benzamide to benzonitrile

Sivakumar,Senthilkumar,Pandit

, p. 2583 - 2587 (2001)

Enhancement of the reaction rate by combining the beneficial effects of PTC and ultrasound has been explored in the present study by taking the transformation of benzamide by dehydration to give benzonitrile as a model system. It was found that there is a

A novel synthesis of 1,2,4-oxadiazoles and isoxazoles

Kivrak, Arif,Zora, Metin

, p. 817 - 831 (2014)

A novel synthesis of 1,2,4-oxadiazoles and isoxazoles is described by utilizing the reactions between amidoximes and α,β-alkynic aldehydes and/or ketones. Conjugate addition products, obtained from amidoximes and α,β-alkynic aldehydes and/or ketones, afford 1,2,4-oxadiazoles and isoxazoles when treated with bases and acids, respectively. 1,2,4-Oxadiazoles can also be synthesized directly from amidoximes and α,β-alkynic aldehydes in a one-pot manner under basic conditions. The reactions are general for a variety of starting compounds and tolerate the presence of aryl, heteroaryl and alkyl groups.

-

Cantacuzene et al.

, p. 1365 (1967)

-

Production of Hydrogen Cyanide by the Ammonia Reforming of Toluene

Weigert, Frank

, p. 97 - 98 (1980)

HCN can be produced from toluene and ammonia in the presence of hydrogen faujasite zeolites at high temperature.

Microwave assisted, solvent free one pot synthesis of nitriles from aryl aldehydes on melamin formaldehyde as solid support

Rezaei, Ramin,Mohammadi, Mohammad Kazem,Rastin, Nedaa

, p. 993 - 996 (2010)

Various aryl aldehydes underwent prompt one pot conversion into the corresponding nitriles in high yields by reacting with hydroxylamine hydrochloride supported on melamine formaldehyde under microwave irradiation in the presence of ammonium acetate as catalyst.

-

Blatt

, p. 91,98 (1938)

-

Electrochemical Behaviour of Diazirines

Elson, Clive M.,Liu, Michael T. H.

, p. 415 - 416 (1982)

The electrochemical reductions of 3-aryl-3-chlorodiazirines and 3-n-butyl-3-phenyldiazirine have been studied by cyclic voltammetry and controlled potential electrolysis in acetonitrile.

Molecular Rearrangements. XXIX. Thermolysis of Aromatic Ketoximes

Badr, M.Z.A.,Aly, M.M.,Mahgoub, S.A.,Fahmy, A.M.,Atallah, A.A.

, p. 1779 - 1784 (1988)

Thermolysis of benzophenone O-benzoyloxime leads to the formation of NH3, CO2, benzene, biphenyl, benzophenone, benzanilide, benzonitrile, benzoic acid, 2-phenylbenzoxazole, salicylaldehyde and its p-isomer.Analogous results were also obtained on thermolysis of acetophenone O-benzoyloxime.Similarly, benzophenone and/or acetophenone O-benzyloximes give pyrolysis products of the same nature in addition to others corresponding to the benzyl moiety.Thermolysis of deoxybenzoin oxime gives NH3, toluene, benzonitrile, bibenzyl, benzil, benzyl alcohol, and 2-phenylindole.Moreover, its O-benzoyl ether affords in addition to these products, benzoic acid and benzyl benzoate.The main feature of these pyrolyses is the homolysis of the N-O bond together with either O-benzyl or O-benzoyl bonds providing free radicals that undergo different reactions involving H-abstraction, dimerization, fragmentation, rearrangement and cyclization to form the identified products.

A thiophosphoryl chloride assisted transformation of arylaldoximes to thioamides

Pandey, Lokesh Kumar,Pathak, Uma,Mathur, Sweta,Suryanarayana

, p. 377 - 379 (2012)

Primary benzothioamides were accessed from benzaldoximes (benzaldehyde oximes) via benzonitriles in a sequential tandem approach utilizing thiophosphoryl chloride as a dehydrating and thionating agent. Georg Thieme Verlag Stuttgart New York.

Ru@UiO-66(Ce) catalyzed acceptorless dehydrogenation of primary amines to nitriles: The roles of Lewis acid-base pairs in the reaction

Lu, Guo-Ping,Li, Xinxin,Zhong, Lixiang,Li, Shuzhou,Chen, Fei

, p. 5386 - 5393 (2019)

UiO-66(Ce)-encapsulated ruthenium nanoparticles (Ru@UiO-66(Ce)) was designed and used for dehydrogenation of primary amines to nitriles in water without any hydrogen acceptors and additives. Introduction of metal Ru to UiO-66(Ce) contributes to the formation of Lewis acid-base pairs on the catalyst owing to the metal-support interaction, acting as active sites for activation of amines and transfer of hydrogen. Ab initio calculation results further confirm the roles of Lewis acid-base pairs in the reaction.

Quantum Dots in Visible-Light Photoredox Catalysis: Reductive Dehalogenations and C-H Arylation Reactions Using Aryl Bromides

Pal, Anuushka,Ghosh, Indrajit,Sapra, Sameer,K?nig, Burkhard

, p. 5225 - 5231 (2017)

In the recent past, visible-light-mediated photoredox catalysis has made a huge impact on the development of new synthetic methods under very mild and ecologically benign conditions. Although semiconductor nanocrystals or quantum dots (QDs) possess suitable optoelectronic and redox properties for photoredox catalytic applications, surprisingly, their use for the activation of challenging chemical bonds in the synthesis of organic molecules is little explored. We report here the application of ZnSe/CdS core/shell QDs for the synthetically important photoredox catalytic activation of carbon-halogen bonds in dehalogenation and C-H arylation reactions using (hetero)aryl halides as bench-stable inexpensive bulk starting materials, under very mild reaction conditions. The outstanding catalytic activity of ZnSe/CdS core/shell QDs is a direct consequence of the high specific surface area and homogeneity of QDs in solution and their high photostability toward oxidation.

Straightforward zinc-catalyzed transformation of aldehydes and hydroxylamine hydrochloride to nitriles

Enthaler, Stephan,Weidauer, Maik,Schr?der, Fanny

, p. 882 - 885 (2012)

In the present study, the zinc-catalyzed dehydration of a range of in situ generated aldoximes, available by the reaction of aldehydes and hydroxylamine hydrochloride, has been explored. After investigating various reaction parameters, with Zn(OTf)2 an excellent and easily accessible pre-catalyst was obtained. The system was highly active and dehydrated a broad range of aldoximes selectively to the corresponding nitriles under mild reaction conditions.

Catalytic oxidative conversion of alcohols, aldehydes and amines into nitriles using KI/I2-TBHP system

Rajender Reddy,Uma Maheswari,Venkateshwar,Prashanthi,Lakshmi Kantam

, p. 2050 - 2053 (2009)

The oxidative conversion of alcohols, aldehydes and amines to give corresponding nitriles in excellent yields was easily achieved by the catalytic amount of KI or I2 in combination with TBHP as an external oxidant. This non-transition metal catalyst is cost effective and provides easy work-up and separation of the product.

A photoresponsive palladium complex of an azopyridyl-triazole ligand: light-controlled solubility drives catalytic activity in the Suzuki coupling reaction

Gazdag, Tamás,Holczbauer, Tamás,Jablonkai, István,Kalapos, Péter Pál,Kunfi, Attila,London, Gábor,Mayer, Péter J.,Németh, Krisztina

, p. 23419 - 23429 (2021)

Herein, the design and synthesis of a click-derived Pd-complex merged with a photoswitchable azobenzene unit is presented. While in thetrans-form of the switch the complex showed limited solubility, the photogeneratedcis-form rendered the molecule soluble in polar solvents. This light-controllable solubility was exploited to affect the catalytic activity in the Suzuki coupling reaction. The effect of the substrate and catalyst concentration and light intensity on the proceeding and outcome of the reaction was studied. Dehalogenation of the aryl iodide starting material was found to be a major side reaction; however, its occurrence was dependent on the applied light intensity.

OsO4-mediated conversion of primary amines to nitriles

Gao,Herzig,Wang

, p. 544 - 546 (2001)

Nitriles are very important intermediates in synthetic organic chemistry. Herein, we report our observation that certain primary amines can be converted to nitriles by trimethylamine N-oxide (TMO) under mild conditions in the presence of a catalytic amount of OsO4. Such a reaction could be used for synthetic purposes as well as for the analysis of functional group compatibility in designing reactions involving OsO4.

Diverse Reactivity of Diazatitanacyclohexenes: Coupling Reactions of 2 H-Azirines Mediated by Titanium(II)

Desnoyer, Addison N.,See, Xin Yi,Tonks, Ian A.

, p. 4327 - 4331 (2018)

2H-Azirines are versatile coupling partners for the synthesis of N-heterocycles. Herein, we present our studies on the reactivity of Cp2Ti(BTMSA) (1; BTMSA = bis(trimethylsilyl)acetylene) with a variety of azirines. In all the cases examined, the initial organometallic products formed are diazatitanacyclohexenes, presumably formed via oxidative addition of Ti(II) into the C-N bond of the azirine to form an azatitanacyclobutene intermediate, followed by C=N insertion of a second equivalent of azirine into the Ti-C bond to form the observed products. Diazatitanacyclohexene 3, bearing phenyl substituents and derived from 2,3-diphenyl-2H-azirine, fragments to form an azabutadiene and nitrile, which is shown to be catalytic in the presence of excess 2,3-diphenyl-2H-azirine. H-substituted complex 8, derived from 3-phenyl-2H-azirine, decomposes via protonolysis of the Cp ligands. In contrast, the methyl-substituted diazatitanacyclohexene 10, derived from 2-methyl-3-phenyl-2H-azirine, is thermally robust. Attempts to trap the putative azatitanacyclobutene intermediate with an alkyne were unsuccessful, resulting instead in the formation of titanacyclopentadiene (12) from coupling of alkyne with BTMSA. Initial reactivity studies found that 10 could be protonolyzed with AcOH to form mixtures of pyrrole and aziridine products, whereas reacting 10 with MeOH results solely in the formation of 2,4-dimethyl-3,5-diphenyl-1H-pyrrole.

CN-Dimeric ortho-palladated complex catalyzed cyanation of aryl halides under microwave irradiation

Hajipour, Abdol Reza,Rafiee, Fatemeh

, p. 1391 - 1395 (2014)

The catalytic activity of dimeric [Pd{C6H2(CH 2CH2NH2)-(OMe)2,2,3}(m-Br)] 2 complex was investigated in the synthesis of benzonitriles under microwave irradiation conditions. The substituted benzonitriles were produced from various aryl halides in excellent yields and short reaction times using a catalytic amount of this complex as efficient, stable and air- and moisture-tolerant catalyst, and K4[Fe(CN)6] as a green cyanide source in DMF at 130 °C.

Direct synthesis of nitriles from aldehydes with hydroxylamine-O-sulfonic acid in acidic water

Quinn, Dylan J.,Haun, Graham J.,Moura-Letts, Gustavo

, p. 3844 - 3847 (2016)

Herein is reported the selective transformation of aldehydes to nitriles in the presence of hydroxylamine-O-sulfonic acid (NH2OSO3H) as a source of the N atom and acidic water. The reaction works with high yields for a large array of aromatic and aliphatic aldehydes, as well as hindered aldehydes and conjugated aldehydes without purification. The reaction conditions are very mild and tolerate a wide array of functional groups. In principle, the reaction can be completed in vinegar.

Activity enhancement in cyanation of aryl halides through confinement of ionic liquid in the nanospaces of SBA-15 -supported Pd complex

Karimi, Babak,Zamani, Asghar,Mansouri, Fariborz

, p. 57639 - 57645 (2014)

A novel and practical ionic-liquid mediated route for the synthesis of various aromatic nitriles has been developed via the cyanation of aryl halides with K4[Fe(CN)6] as a low cost, non-toxic and easily handled cyanating reagent in the presence of SBA-15 functionalized palladium complex partially confined with ionic liquids (IL@SBA-15-Pd) as the catalyst. Among the various ionic liquids tested in the cyanation reaction, 1-butyl-3-methylimidazolium hexafluorophosphate was found to provide the best medium for Pd-catalyzed cyanation of aryl halides. A variety of electron-rich and electron-poor aryl iodides and bromides gave the corresponding benzonitrile derivatives in good yield. Moreover, the catalyst was reused in four consecutive cycles with consistent catalytic activity. It was found that the presence of ionic liquid in the mesochannels of the mesoporous support not only provides a means of stabilizing Pd nanoparticles during the reaction but also the salient phase transfer feature of the imidazolium moieties may also serve as handles for faster penetration of Fe(CN)63- into the system pores to achieve highly concentrated reaction sites in close proximity to the catalytic (Pd NPs) centers, which resulted in an enhancement of the catalyst activity performance. This journal is

Copper immobilized on aminated ferrite nanoparticles by 2-aminoethyl dihydrogen phosphate (Fe3O4@AEPH2-CuII) catalyses the conversion of aldoximes to nitriles

Zarghani, Monireh,Akhlaghinia, Batool

, p. 683 - 689 (2015)

CuII immobilized on aminated ferrite nanoparticles by 2-aminoethyl dihydrogen phosphate (Fe3O4@AEPH2-CuII) was prepared and characterized using FT-IR, TGA, TEM, EDX, VSM, XRD, CHN and ICP techniques. The easily prepared heterogeneous nanocatalyst demonstrated a significant catalytic performance for the transformation of aldoximes to nitriles that is far superior to previously reported methods. The reaction allows for the conversion of a wide variety of aldoximes including aromatic, aliphatic and heterocyclic aldoximes in good to excellent yields (50-98%). High efficiency, mild reaction conditions, easy work-up, operational simplicity, simple purification of products and safe handling of the catalyst are important advantages of this method. In addition, the environmentally benign heterogeneous nanocatalyst can be easily recovered from reaction mixtures using an external magnet and reused several times without any loss of activity.

-

Wislicenus,Goldschmidt

, p. 1471 (1900)

-

Tetrabutylammonium peroxydisulfate in organic synthesis. Part 8. An efficient and convenient nickel-catalyzed oxidation of primary amines to nitriles with tetrabutylammonium peroxydisulfate

Chen, Fen-Er,Peng, Zuo-Zhong,Fu, Han,Liu, Ji-Dong,Shao, Lan-Ying

, p. 726 - 727 (1999)

A series of primary amines are oxidized to corresponding nitriles in excellent yields with tetrabutylammonium peroxydisulfate catalyzed by nickel copper formate under basic aqueous conditions.

Highly selective aerobic oxidation of primary amines to nitriles by ruthenium hydroxide

Zhang, Yuan,Xu, Kunling,Chen, Xiaorong,Hu, Tongjie,Yu, Yanpeng,Zhang, Junli,Huang, Jun

, p. 951 - 954 (2010)

A highly selective ruthenium catalyzed aerobic oxidation of primary amines to corresponding nitriles was developed in water and organic solvents. The catalyst system was highly efficient and widely applicable, and several functional groups were tolerated under the reaction conditions employed.

A CONVENIENT SRN1 SYNTHESIS OF AROMATIC NITRILES FROM DIAZONIUM SALTS VIA DIAZOSULFIDES

Petrillo, Giovanni,Novi, Marino,Garbarino, Giacomo,Dell'erba, Carlo

, p. 4625 - 4634 (1987)

Properly substituted diazosulfides XC6H4-N=N-SPh (1) (either isolated or generated in situ from arenediazonium tetrafluoroborates and sodium benzenethiolate) react with tetrabutylammonium cyanide, in Me2SO under photon or electron stimulation, leading to nitriles XC6H4CN (2).Satisfactory yields of 2, comparable with those of the Sandmeyer reaction, are obtained when X= 3- or 4-CF3, 2-, 3-, or 4-CN, 4-F, 4-MeCO, 3-MeO, 4-NO2, 4-PhCO, and 4-PhSO2.For different reasons, the reaction practically fails as a useful nitrile synthesis when X= H, 4-MeO, 2-, or 3-NO2.The collected evidences agree well with the intervention of an SRN1 mechanism to which diazosulfides 1, given their easy reducibility followed by a prompt fragmentation of the C-N and N-S bonds, are convenient participating substrates.An important consequence of the mechanism involved is the behaviour of bromo and chloro derivatives (1: X= Br, Cl) which lead, through the contemporaneous introduction of two cyano functionalities, to more than satisfactory yields of the corresponding dicyanobenzenes.

Highly dispersed Co species in N-doped carbon enhanced the aldehydes ammoxidation reaction activity

Fu, Wenqian,Pan, Liuming,Tang, Tiandi,Wang, Siming,Zhang, Lei

, (2022/01/04)

Developing environmentally friendly catalysts with high activity for the ammoxidation of aromatic aldehydes to aromatic nitriles is greatly important for this industrial transformation. Herein, natural vitamin B12 was used as a carbon source for the preparation of a cobalt- and nitrogen-doped catalyst precursor, which was pyrolyzed at different temperatures to obtain cobalt- and nitrogen-doped carbon (Co@NC-T) (T denotes pyrolysis temperature) catalysts. The Co@NC-800 exhibited excellent activity and selectivity in the ammoxidation of aromatic aldehydes with ammonium carbonate to aromatic nitriles compared to the Co@NC-700, Co@NC-600 and Co@NC-500 catalysts. The high catalytic performance of Co@NC-800 could be due to the presence of the low-density electron cloud of the highly dispersed Co species, which could interact with the benzene ring of benzaldehyde bearing p-π conjugate, thereby promoting the adsorption and activation of benzaldehyde. Consequently, the activated benzaldehyde reacted with amino groups that were decomposed from ammonium carbonate and subsequently underwent a dehydration process to form nitriles.

Preparation of nitriles from aldehydes using ammonium persulfate by means of a nitroxide-catalysed oxidative functionalisation reaction

León Sandoval, Arturo,Leadbeater, Nicholas E.,Politano, Fabrizio,Witko, Mason L.

supporting information, p. 667 - 671 (2022/01/28)

A methodology for the preparation of nitriles from aldehydes by means of an oxidative functionalisation reaction is reported. It employs ammonium persulfate as both the primary oxidant and the nitrogen source, and a catalytic amount of a nitroxide. It is applicable to a range of structurally diverse (hetero)aromatic aldehydes furnishing the nitrile products in 30-97% isolated yield. Given the ready accessibility of aldehydes and that ammonium persulfate is cheap and less toxic than many other reagents for generating nitriles, this methodology offers a simple and easy to use approach to this valuable class of compounds. This journal is

Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors

Sharma, Brijesh M.,Nikam, Arun V.,Lahore, Santosh,Ahn, Gwang-Noh,Kim, Dong-Pyo

supporting information, (2022/02/25)

This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound mask

Construction of N-Acyliminophosphoranes via Iron(II)-Catalyzed Imidization of Phosphines with N-Acyloxyamides

Lin, Sen,Lin, Bo,Zhang, Zongtao,Chen, Jianhui,Luo, Yanshu,Xia, Yuanzhi

, p. 3302 - 3306 (2022/05/05)

Employing FeCl2as a cheap and readily available catalyst, a facile imidization of phosphines with N-acyloxyamides is described, affording synthetically useful N-acyliminophosphoranes with high functional group tolerance. The transformation is easily performed under an air atmosphere at room temperature and could be scaled up to gram scale with a catalyst loading of 1 mol %. The iminophosphoranyl moiety in the product was further utilized as an effective directing group for controllable ortho C(sp2)-H bond amidations under Rh(III) catalysis.

Wavelength-Specific Product Desorption as a Key to Raising Nitrile Yield of Primary Alcohol Ammoxidation over Illuminated Pd Nanoparticles

Han, Pengfei,Tang, Cheng,Sarina, Sarina,Waclawik, Eric R.,Du, Aijun,Bottle, Steven E.,Fang, Yanfen,Huang, Yingping,Li, Kun,Zhu, Huai-Yong

, p. 2280 - 2289 (2022/02/14)

Research on visible-light photocatalysts of metal nanoparticles (NPs) has focused on increasing the reactant conversion by light-excited charges (electrons and positively charged holes). However, light irradiation can accelerate catalysis by other mechanisms. Here, we report that 650 nm wavelength irradiation of 0.75 W·cm-2 significantly increases nitrile yield of ammoxidation of primary aromatic alcohols with an ammonium salt over supported Pd NPs at 80 °C in air. We found that the desorption of the nitrile product from the catalyst is the rate-determining step; the irradiation promotes not only alcohol oxidation and subsequent aldehyde cyanation over the Pd NPs but also the nitrile desorption selectively via resonance energy transfer to achieve a high nitrile yield. This new mechanism provides a knob for the exquisite control of catalytic reaction pathways for ecofriendly synthesis.

Process route upstream and downstream products

Process route

N-benzylbenzamide
1485-70-7

N-benzylbenzamide

benzyl bromide
100-39-0

benzyl bromide

benzonitrile
100-47-0

benzonitrile

Conditions
Conditions Yield
With phosphorus pentabromide;
2-benzylbenzamide
40182-20-5

2-benzylbenzamide

benzyl bromide
100-39-0

benzyl bromide

benzonitrile
100-47-0

benzonitrile

Conditions
Conditions Yield
With phosphorus pentabromide;
<i>N</i>-(4-phenoxy-butyl)-benzamide

N-(4-phenoxy-butyl)-benzamide

(4-chlorobutoxy)benzene
2651-46-9

(4-chlorobutoxy)benzene

benzonitrile
100-47-0

benzonitrile

Conditions
Conditions Yield
With phosphorus pentachloride; Destillation des entstandenen Imidchlorids;
benzaldehyde-((<i>E</i>)-<i>O</i>-[1]naphthylcarbamoyl oxime ); α-naphthylcarbamic acid-derivative of β-benzaldoxime

benzaldehyde-((E)-O-[1]naphthylcarbamoyl oxime ); α-naphthylcarbamic acid-derivative of β-benzaldoxime

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

1,3-dinaphthalen-1-ylurea
607-56-7

1,3-dinaphthalen-1-ylurea

1-amino-naphthalene
134-32-7

1-amino-naphthalene

benzonitrile
100-47-0

benzonitrile

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
benzoin oxime
441-38-3

benzoin oxime

5-nitrobarbituric acid
611-08-5,28806-18-0

5-nitrobarbituric acid

benzaldehyde
100-52-7

benzaldehyde

benzonitrile
100-47-0

benzonitrile

Conditions
Conditions Yield
With triethylamine; 2,4-Dichloro-5-nitropyrimidine; In acetonitrile; for 5h; Product distribution; Heating;
50%
65%
3-azido-1,2,3-triphenylcyclopropene
39672-25-8

3-azido-1,2,3-triphenylcyclopropene

2,3-diphenyl-1H-inden-1-one
1801-42-9

2,3-diphenyl-1H-inden-1-one

benzonitrile
100-47-0

benzonitrile

diphenyl acetylene
501-65-5

diphenyl acetylene

(E)-2-phenylchalcone
7474-65-9,7512-67-6,4023-77-2

(E)-2-phenylchalcone

Conditions
Conditions Yield
With diiron nonacarbonyl; In methanol; for 24h; Ambient temperature;
1%
1%
67%
With diiron nonacarbonyl; In acetonitrile; for 24h; Ambient temperature;
5%
9%
15%
With diiron nonacarbonyl; In acetonitrile; Product distribution; Ambient temperature;
5%
15%
9%
With diiron nonacarbonyl; In benzene; for 24h; Ambient temperature;
6%
8%
8%
2,6-diphenyl-4-phenylsulfonylimino-5,6-dihydro-4,1,3-selenaoxazine
87786-72-9

2,6-diphenyl-4-phenylsulfonylimino-5,6-dihydro-4,1,3-selenaoxazine

triphenylphosphine
603-35-0

triphenylphosphine

P,P,P-triphenyl-N-phenylsulfonylphosphine imide
1056-25-3

P,P,P-triphenyl-N-phenylsulfonylphosphine imide

benzonitrile
100-47-0

benzonitrile

Conditions
Conditions Yield
In benzene; for 6h; Heating;
91%
ethanedinitrile
460-19-5,25215-76-3

ethanedinitrile

salicylonitrile
611-20-1

salicylonitrile

m-cyanophenol
873-62-1

m-cyanophenol

4-cyanophenol
767-00-0

4-cyanophenol

benzonitrile
100-47-0

benzonitrile

Conditions
Conditions Yield
Yield given. Further byproducts given. Yields of byproduct given; gaseous plasma of glow discharge;
ethanedinitrile
460-19-5,25215-76-3

ethanedinitrile

salicylonitrile
611-20-1

salicylonitrile

hydrogen cyanide
74-90-8

hydrogen cyanide

m-cyanophenol
873-62-1

m-cyanophenol

4-cyanophenol
767-00-0

4-cyanophenol

benzonitrile
100-47-0

benzonitrile

Conditions
Conditions Yield
Product distribution; plasma apparatus; a variety of substituted benzenes and pyridine similarly cyanated;
18 % Chromat.
10 % Chromat.
8.3 % Chromat.
9.0 % Chromat.
N-benzylbenzamide
1485-70-7

N-benzylbenzamide

phosphorus pentabromide
7789-69-7

phosphorus pentabromide

benzyl bromide
100-39-0

benzyl bromide

benzonitrile
100-47-0

benzonitrile

Conditions
Conditions Yield
gibt ein Reaktionsprodukt das bei der Destillation im Vakuum;

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