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Cas Database

1003-31-2

1003-31-2

Identification

Synonyms:2-Cyanothiophene;2-Thienonitrile;2-Thienylcarbonitrile;Thiophene-2-carbonitrile;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,IrritantXi,FlammableF

  • Hazard Codes:Xn,Xi,F

  • Signal Word:Danger

  • Hazard Statement:H226 Flammable liquid and vapourH302 Harmful if swallowed H315 Causes skin irritation H318 Causes serious eye damage H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. 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. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers 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. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • 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
  • Product Description:2-Thiophenecarbonitrile
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Cyanothiophene >98.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Cyanothiophene >98.0%(GC)
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Thiophene-2-carbonitrile
  • Packaging:25 g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Thiophene-2-carbonitrile
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Thiophenecarbonitrile 99%
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  • Manufacture/Brand:Oakwood
  • Product Description:2-Thiophenecarbonitrile 99%
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Relevant articles and documentsAll total 239 Articles be found

DMF-catalysed thermal dehydration of aldoximes: A convenient access to functionalized aliphatic and aromatic nitriles

Supsana, Paraskevi,Liaskopoulos, Theodoras,Tsoungas, Petros G.,Varvounis, George

, p. 2671 - 2674 (2007)

N,N-Dimethylformamide was found to act as solvent and catalyst in the dehydration of aldoximes to nitriles. The reaction required heating at 135°C and yields of nitriles were moderate to good. (Benzylideneaminooxy)formaldehyde was detected as an intermediate in one of the reactions. Georg Thieme Verlag Stuttgart.

Per-6-amino-β-cyclodextrin/CuI catalysed cyanation of aryl halides with K4[Fe(CN)6]

Azath, Ismail Abulkalam,Suresh, Palaniswamy,Pitchumani, Kasi

, p. 2334 - 2339 (2012)

Efficient cyanation of aryl halides is achieved using less toxic K 4[Fe(CN)6] as the reagent and amino-β-cyclodextrins as supramolecular ligands for CuI. Four different amino cyclodextrins viz. per-6-amino-β-CD, per-6-methylamino-β-CD, per-6-butyl-amino-β-CD and mono-6-amino-β-CD are prepared and studied. Aryl and heteroaryl nitriles are obtained in good to excellent yield for even bromo derivatives of flavone and 2-aminopyrans. This system uses catalytic amounts (10 mol%) of both copper iodide and per-6-amino-β-cyclodextrin. Easy separation, the absence of nitrogen atmosphere and excellent yield are the other significant outcomes of this protocol. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Palladium nanoparticles stabilized by a copolymer of N-vinylimidazole with N-vinylcaprolactam as efficient recyclable catalyst of aromatic cyanation

Beletskaya,Selivanova,Tyurin,Matveev,Khokhlov

, p. 157 - 161 (2010)

A new recyclable catalytic system was developed based on palladium nanoparticles and a copolymer of N-vinylimidazole and N-vinylcaprolactam for cyanation of aromatic bromides. The source of the cyanide ion was a nontoxic potassium hexacyanoferrate.

SYNTHESIS OF 3-THIENYL-SUBSTITUTED ISOTHIAZOLINES-2- AND 1,2,4-THIADIAZOLES BASED ON NITRILE SULFIDES OF THE THIOPHENE SERIES

Krayushkin, M. M.,Kalik, M. A.,Kudryavtseva, A. Ya.

, p. 1477 - 1481 (1992)

The reaction of substituted α- and β-thienylcarboxamides with chlorocarbonylsulfenyl chloride gave 5-thienyl-substituted 1,3,4-oxathiazol-2-ones.Decarboxylation of the latter by heating in o-dichlorobenzene generated in situ α- and β-thienylnitrile sulfid

Direct Conversion of Benzyl Ethers into Aryl Nitriles

Tian, Xinzhe,Ren, Yun-Lai,Ren, Fangping,Cheng, Xinqiang,Zhao, Shuang,Wang, Jianji

, p. 2444 - 2448 (2018)

A direct method was developed for the conversion of benzyl ethers into aryl nitriles by using NH 4 OAc as the nitrogen source and oxygen as the terminal oxidant with catalysis by TEMPO/HNO 3; the method is valuable for both the synthesis of aromatic nitriles and for the deprotection of ether-protected hydroxy groups to form nitrile groups in multistep organic syntheses.

Selectivity-tunable amine aerobic oxidation catalysed by metal-free N,O-doped carbons

Li, Yingguang,Shang, Sensen,Wang, Lianyue,Lv, Ying,Niu, Jingyang,Gao, Shuang

, p. 12251 - 12254 (2019)

Herein, we present a series of N,O-doped mesoporous carbons obtained at different pyrolysis temperatures as the first metal-free catalysts which successfully switch between imine and nitrile products for amine oxidation. Systematic characterization studies and control experiments revealed that the C-O group on the surface could function as a catalytically active site for nitrile synthesis and the N-doping environment was essential.

Metal-free one-pot conversion of electron-rich aromatics into aromatic nitriles

Ushijima, Sousuke,Togo, Hideo

, p. 1067 - 1070 (2010)

Various electron-rich aromatics could be smoothly converted into the corresponding aromatic nitriles in good to moderate yields by treatment of electron-rich aromatics with POCl3 and DMF, followed by treatment with molecular iodine in aqueous ammonia. The present reaction is a novel metal-free one-pot method for the preparation of aromatic nitriles from electron-rich aromatics.

Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate) catalyzed Suzuki, Heck, Sonogashira, and cyanation reactions

Nandurkar, Nitin S.,Bhanage, Bhalchandra M.

, p. 3655 - 3660 (2008)

Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate): a structurally well-defined O-containing transition metal complex is reported as an efficient catalyst for Suzuki, Heck, and Sonogashira cross-coupling reactions. The protocol was also applied successfully for cyanation of aryl halides under milder operating conditions. The system tolerated the coupling of various aryl halides with alkenes, alkynes, and organoboronic acid along with the cyanation of aryl halides providing good to excellent yields of desired products.

A clean conversion of aldehydes to nitriles using a solid-supported hydrazine

Baxendale, Ian R.,Ley, Steven V.,Sneddon, Helen F.

, p. 775 - 777 (2002)

A polymer-supported hydrazine reagent has been applied to the conversion of a range of aldehydes to nitriles, providing a clean and efficient route to more diverse building blocks for combinatorial chemistry programmes.

A one-pot conversion of carboxylic acids into nitriles catalysed by PEG400 under microwave irradiation

Cao, Yu-Qing,Qu, An-Li,Liu, Rui-Yan,Duan, Chun-Ming

, p. 414 - 415 (2010)

A new efficient method for the synthesis of nitriles is reported. Carboxylic acids were converted into nitriles by a onepot reaction with hydroxylamine sulfate and zinc catalysed by PEG400 under microwave irradiation in excellent yields. The most suitable condition was 20 minutes under the microwave power of 231 W with 5 mol% PEG400.

NH3?H2O: The Simplest Nitrogen-Containing Ligand for Selective Aerobic Alcohol Oxidation to Aldehydes or Nitriles in Neat Water

Zhang, Guofu,Ma, Danting,Zhao, Yiyong,Zhang, Guihua,Mei, Guangyao,Lyu, Jinghui,Ding, Chengrong,Shan, Shang

, p. 885 - 889 (2018)

Aqueous ammonia (NH3?H2O) has been shown to serve as the simplest nitrogen-containing ligand to effectively promote copper-catalyzed selective alcohol oxidation under air in water. A series of alcohols with varying electronic and steric properties were selectively oxidized to aldehydes with up to 95 % yield. Notably, by increasing the amount of aqueous ammonia in neat water, the exclusive formation of aryl nitriles was also accomplished with good-to-excellent yields. Additionally, the catalytic system exhibits a high level of functional group tolerance with ?OH, ?NO2, esters, and heteroaryl groups all being amenable to the reaction conditions. This one-pot and green oxidation protocol provides an important synthetic route for the selective preparation of either aldehydes or nitriles from commercially available alcohols.

Aerobic Oxidative Conversion of Aromatic Aldehydes to Nitriles Using a Nitroxyl/NOx Catalyst System

Noh, Ji-Hyun,Kim, Jinho

, p. 11624 - 11628 (2015)

The first transition-metal-free aerobic oxidative conversion of aldehyde catalyzed by a nitroxyl radical/NOx system is presented for the synthesis of nitrile. In the presence of a catalytic amount of 4-AcNH-TEMPO (4-acetamido-2,2,6,6-tetramethylpiperidine-N-oxyl), NaNO2, and HNO3, benzaldehydes bearing a variety of functional groups underwent condensation with NH4OAc and following aerobic oxidation to produce nitriles selectively under an O2 balloon. Aerobic oxidative conversion of a primary alcohol instead of aldehyde is also achieved by a one-pot sequential strategy.

New applications of Ph3P=N-Li in organic synthesis and heteroatom chemistry

Taillefer, Marc,Rahier, Nicolas,Minta, Ewelina,Cristau, Henri-Jean

, p. 1847 - 1850 (2002)

The lithium triphenylaminophosphonium azayldiide 1 proved again to be a very good tool in organic synthesis, allowing further synthesis of various compounds such as vinyl nitriles, aromatic or heteroaromatic nitriles, and mono-, bis-, and trisphosphinimines.

-

Meltzer et al.

, p. 4062,4064 (1955)

-

CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source

Ren, Yun-Lai,Shen, Zhenpeng,Tian, Xinzhe,Xing, Ai-Ping,Zhao, Zhe

, (2021)

Readily available CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C[tbnd]N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.

A Mild, High-Yield Conversion of Aldoximes into Nitriles using Trichloroacetyl Chloride/Triethylamine

Saednya, Akbar

, p. 748 - 749 (1983)

-

Pd/Mn Bimetallic Relay Catalysis for Aerobic Aldoxime Dehydration to Nitriles

Zhang, Dongliang,Huang, Yaping,Zhang, Erlei,Yi, Rong,Chen, Chao,Yu, Lei,Xu, Qing

, p. 784 - 790 (2018)

A Pd/Mn bimetal system was found to be an effective catalyst for dehydration of aldoximes to the useful nitriles under mild aerobic conditions. Different to the known metal-catalyzed aldoxime dehydration reactions, this reaction very possibly proceeded via an alternative mechanism of Pd/Mn bimetal relay catalysis involving a Mn-catalyzed aerobic oxidation of aldoximes to nitrile oxides by air and a Pd-catalyzed oxygen transfer from the nitrile oxides to the solvent acetonitrile. This method tolerates a variety of substrates including sterically bulky ones and also the natural product derivative. (Figure presented.).

Br?nsted Acid Catalyzed Nitrile Synthesis from Aldehydes Using Oximes via Transoximation at Ambient Temperature

Hyodo, Kengo,Togashi, Kosuke,Oishi, Naoki,Hasegawa, Genna,Uchida, Kingo

, p. 3005 - 3008 (2017)

The Br?nsted acid-catalyzed synthesis of nitriles is described via transoximation under mild conditions using an O-protected oxime as a more stable equivalent of explosive O-protected hydroxylamines. The nitrile was generated via an O-protected aldoxime produced from the aldehyde and an O-protected oxime through transoximation. The reaction could be performed on a 1 g scale.

Influence of alkyl side chain on the crystallinity and trap density of states in thiophene and thiazole semiconducting copolymer based inkjet-printed field-effect transistors

Lee, Jiyoul,Chung, Jong Won,Jang, Jaeman,Kim, Do Hwan,Park, Jeong-Il,Lee, Eunkyung,Lee, Bang-Lin,Kim, Joo-Young,Jung, Ji Young,Park, Joon Seok,Koo, Bonwon,Jin, Yong Wan,Kim, Dae Hwan

, p. 1927 - 1934 (2013)

The influence of alkyl side chains on the crystallinity of semiconducting copolymer films and their sub-bandgap density-of-states (DOS), the latter being closely related to the stability and the device performance of organic field-effect transistors (OFETs), is investigated. Three different poly(hexathiophene-alt-bithiazole) (PHTBTz) based polymer semiconductors, with identical backbones but different side chain positions and lengths, were synthesized. The crystallinity examined by grazing incidence X-ray diffraction (GIXRD) strongly depends on the number, position, and length of each type of alkyl side chain attached to the thiophene and thiazole copolymer backbones. Also, the sub-bandgap trap DOS distributions were extracted by performing multiple-frequency capacitance-voltage (MF-CV) spectroscopy on the field effect devices. The relationship between film crystallinity and trap DOS in the field-effect transistors can be interpreted in terms of the complex interplay between the number, position, and length of each alkyl side chain for efficient π-π stacking. In particular, the number and position of the alkyl side chain attached to the polymer backbone significantly affects the device performance. Poly(tetryloctylhexathiophene-alt-dioctylbithiazole) (PHTBTz-C8) exhibits the best electrical performance among the different semiconductors synthesized, with a relatively low bulk trap density of ~2.0 × 10 20 cm-3 eV-1 as well as reasonable hole mobility of ~0.25 cm2 V-1 s-1. The microstructural analyses of this organic material strongly suggest that the short π-π stacking distance induces strong interaction between adjacent polymer backbones, which in turn results in enhanced electrical properties.

Lewis acid promoted dehydration of amides to nitriles catalyzed by [PSiP]-pincer iron hydrides

Chang, Guoliang,Li, Xiaoyan,Zhang, Peng,Yang, Wenjing,Li, Kai,Wang, Yajie,Sun, Hongjian,Fuhr, Olaf,Fenske, Dieter

, (2020)

The dehydration of primary amides to their corresponding nitriles using four [PSiP]-pincer hydrido iron complexes 1–4 [(2-Ph2PC6H4)2MeSiFe(H)(PMe3)2 (1), (2-Ph2PC6H4)2HSiFe(H)(PMe3)2 (2), (2-(iPr)2PC6H4)2HSiFe(H)(PMe3)2 (3) and (2-(iPr)2PC6H4)2MeSiFe(H)(PMe3)2 (4)] as catalysts in the presence of (EtO)3SiH as dehydrating reagent was explored in the good to excellent yields. It was proved for the first time that Lewis acid could significantly promote this catalytic system under milder reaction conditions than other Lewis acid-promoted system, such as shorter reaction time or lower reaction temperature. This is also the first example that dehydration of primary amides to nitriles was catalyzed by silyl hydrido iron complexes bearing [PSiP]-pincer ligands with Lewis acid as additive. This catalytic system has good tolerance for many substituents. Among the four iron hydrides 1 is the best catalyst. The effects of substituents of the [PSiP]-pincer ligands on the catalytic activity of the iron hydrides were discussed. A catalytic reaction mechanism was proposed. Complex 4 is a new iron complex and was fully characterized. The molecular structure of 4 was determined by single crystal X-ray diffraction.

A mild and efficient method for the conversion of aldehydes into nitriles and thiols into disulfides using an ionic liquid oxidant

Hosseinzadeh, Rahman,Golchoubian, Hamid,Nouzarian, Mahboobe

, p. 4713 - 4725 (2015)

A simple, mild and high yielding method for the conversion of various aldehydes to nitriles has been developed using an ionic liquid reagent, hexamethylene bis(N-methylimidazolium) bis(dichloroiodate) (HMBMIBDCI), in combination with aqueous ammonia in CH3CN at room temperature. Moreover, the treatment of aromatic and aliphatic thiols with HMBMIBDCI resulted in the corresponding disulfides in solvent-free condition at room temperature.

Rapid, Easy Cyanation of Aryl Bromides and Chlorides Using Nickel Salts in Conjunction with Microwave Promotion

Arvela, Riina K.,Leadbeater, Nicholas E.

, p. 9122 - 9125 (2003)

We report here a fast, easy, and efficient method for the preparation of aryl nitriles from aryl bromides and chlorides. The methodology for aryl bromides involves the use of either Ni(CN)2 or NaCN and NiBr 2. With aryl chlorides, a mix of NaCN and NiBr2 is used and the reaction proceeds via the in situ formation of the corresponding aryl bromide. The reaction can be performed in air and is complete within 10 min.

AlCl3·6H2O/KI/H2O/CH3CN: A new alternate system for dehydration of oximes and amides in hydrated media

Boruah, Monalisa,Konwar, Dilip

, p. 7138 - 7139 (2002)

Dehydration of oximes and amides to nitriles was carried out using the AlCl3·6H2O/KI/H2O/CH3CN system. It produced isoquinoline derivatives 8a-c (Bischler Naperialski reaction) when reacted with amides 7a-c in hydrated media. Also, the keto oximes produced anilides (Beckmann rearrangement) with the system under the same reaction conditions.

Facile transformation of esters to nitriles

Suzuki, Yusuke,Moriyama, Katsuhiko,Togo, Hideo

, p. 7956 - 7962 (2011)

Various esters were efficiently converted into the corresponding nitriles in good yields by the treatment with sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), followed by treatment with molecular iodine in aq ammonia. The present one-pot method is very efficient and practical for the conversion of various aromatic and aliphatic esters into the corresponding nitriles.

Microwave-induced conversion of aldoximes to nitriles by DBU

Sabitha, Gowravaram,Syamala

, p. 4577 - 4580 (1998)

Aldoximes (1) can be rapidly converted into corresponding nitriles (2) in good yields with a novel reagent DBU under microwave irradiation.

Metal oxide-catalyzed ammoxidation of alcohols to nitriles and promotion effect of gold nanoparticles for one-pot amide synthesis

Ishida, Tamao,Watanabe, Hiroto,Takei, Takashi,Hamasaki, Akiyuki,Tokunaga, Makoto,Haruta, Masatake

, p. 85 - 90 (2012)

Transition metal oxides (MnO2, Co3O4, and NiO) are catalytically active for the ammoxidation of alcohols to nitriles. In particular, MnO2 exhibited remarkably high catalytic activity and selectivity for the ammoxidation of alcohols to produce nitriles. Benzyl alcohol could also be directly converted to benzonitrile by MnO2 catalyst by the one-pot ammoxidation and the hydration with water which was formed by the first ammoxidation step. The deposition of gold nanoparticles (Au NPs) onto MnO2 did not enhance the ammoxidation of benzyl alcohol but promoted the hydration of benzonitrile to produce benzamide with high selectivity. In contrast, Au NPs supported on Al2O3, CuO, and CeO 2 catalyzed the ammoxidation of benzyl alcohol, whereas these metal oxides themselves were inactive for the ammoxidation or showed low catalytic activity. These results have demonstrated that gold is intrinsically active as a catalyst for the ammoxidation of alcohols.

-

Wentrop

, p. 1027,1031 (1971)

-

Tin or gallium-catalyzed cyanide-transition metal-free synthesis of nitriles from aldehydes or oximes

Zhuang, Yan-Jun,Liu, Jie,Kang, Yan-Biao

, p. 5700 - 5702 (2016)

Tin or gallium chloride catalyzed transformation of oximes or aldehydes to nitriles is described. Various nitriles were obtained in up to 99% of yields. The gram-scale reaction or the optically active dinitrile was also available. This synthetically useful method has avoided toxic organic or inorganic cyanides as well as transition or noble metal catalysts.

Postsynthesis-Treated Iron-Based Metal-Organic Frameworks as Selective Catalysts for the Sustainable Synthesis of Nitriles

Rapeyko, Anastasia,Climent, Maria J.,Corma, Avelino,Concepci?n, Patricia,Iborra, Sara

, p. 3270 - 3282 (2015)

The dehydration of aldoximes to the corresponding nitriles can be performed with excellent activity and selectivity by using iron trimesate as a homogeneous catalyst. Iron trimesate has been heterogenized by synthesizing metal-organic frameworks (MOFs) from iron trimesate, that is, Fe(BTC), and MIL-100 (Fe). These materials were active and selective aldoxime dehydration catalysts, and postsynthesis-treated MIL-100 (Fe) produced the desired nitriles with 100 conversion and selectivities >90 under mild reaction conditions and in short reaction times. X-ray photoelectron spectroscopy showed the presence of different Fe species in the catalyst, and in situ IR spectroscopy combined with catalytic results indicates that the catalytic activity is associated with Fe framework species. The postsynthesis-treated MIL-100 (Fe)-NH4F can be recycled several times and has an excellent reaction scope, which gives better catalytic results than other solid acid or base catalysts.

Uniform silver nanoparticles on tunable porous N-doped carbon nanospheres for aerobic oxidative synthesis of aryl nitriles from benzylic alcohols

Hashemi, Alireza Nemati,Eshghi, Hossein,Lamei, Kamran

, (2019)

Tunable N-doped carbon nanospheres from sucrose as carbon source and Tris(2-aminoethyl)amine (TAEA) as nitrogen source by a simple and easily reproducible method were prepared. It was demonstrated that the tunable N-doping of carbon spheres could be realized by altering the ratio of TAEA in the raw materials. The content of doped nitrogen, surface area, pore volume and pore size of carbon nanospheres were increased with the increasing of TAEA amount in the hydrothermal process. Prepared N-doped carbon nanospheres act as solid ligand for anchoring of Ag NPs which generated via chemical reduction of Ag ions. Benzylic alcohols and aldehydes were converted into the aryl nitriles by using Ag/N-CS-1 nanospheres as the catalyst and O2 as the oxidant, efficiently. This catalyst was stable and could use for 6 successful runs.

A Molecular Iron-Based System for Divergent Bond Activation: Controlling the Reactivity of Aldehydes

Chatterjee, Basujit,Jena, Soumyashree,Chugh, Vishal,Weyhermüller, Thomas,Werlé, Christophe

, p. 7176 - 7185 (2021)

The direct synthesis of amides and nitriles from readily available aldehyde precursors provides access to functional groups of major synthetic utility. To date, most reliable catalytic methods have typically been optimized to supply one product exclusively. Herein, we describe an approach centered on an operationally simple iron-based system that, depending on the reaction conditions, selectively addresses either the C=O or C-H bond of aldehydes. This way, two divergent reaction pathways can be opened to furnish both products in high yields and selectivities under mild reaction conditions. The catalyst system takes advantage of iron's dual reactivity capable of acting as (1) a Lewis acid and (2) a nitrene transfer platform to govern the aldehyde building block. The present transformation offers a rare control over the selectivity on the basis of the iron system's ionic nature. This approach expands the repertoire of protocols for amide and nitrile synthesis and shows that fine adjustments of the catalyst system's molecular environment can supply control over bond activation processes, thus providing easy access to various products from primary building blocks.

Microwave promoted rapid dehydration of aldoximes to nitriles using melamine-formaldehyde resin supported sulphuric acid in dry media

Rezaei, Ramin,Karami, Marzeih

, p. 815 - 818 (2011)

A simple and convenient procedure for the synthesis of nitriles by dehydration of aldoxime using supported sulphuric acid on melamine-formaldehyde resin (MFR) under solvent-free condition has been developed. A variety of aromatic and aliphatic aldoximes were converted to the corresponding nitriles. The resin was recovered and reused for subsequent reactions.

One-Flask Conversion of Aldehydes into Nitriles

Saednya, Akbar

, p. 190 - 191 (1982)

-

Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles

Xu, Jiaxi,Gao, Yu,Li, Zhenjiang,Liu, Jingjing,Guo, Tianfo,Zhang, Lei,Wang, Haixin,Zhang, Zhihao,Guo, Kai

, p. 311 - 315 (2020)

Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.

One-pot oxidative conversion of alcohols into nitriles by using a TEMPO/PhI(OAc)2/NH4OAc system

Vatèle, Jean-Michel

, p. 1275 - 1278 (2014)

A direct conversion of alcohols into nitriles with 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO), iodosobenzene diacetate, and ammonium acetate as a nitrogen source is reported. This transformation, which proceeds through an oxidation-imination-aldimine oxidation sequence in situ, has been applied to a range of aliphatic, benzylic, heteroaromatic, allylic, and propargyl alcohols. Highly chemoselective ammoxidation of primary alcohols in the presence of secondary alcohols was also achieved. Georg Thieme Verlag Stuttgart New York.

Conversion of aldoximes into nitriles catalyzed by simple transition metal salt of the fourth period in acetonitrile

Ma, Xiao-Yun,He, Ying,Lu, Ting-Ting,Lu, Ming

, p. 2560 - 2564 (2013)

Conversion of aldoximes into nitriles catalyzed by simple transition metal catalysts, such as copper salts, nickel salts, cobalt salts, zinc salts, iron salts, and manganese salts in acetonitrile was investigated. All the metal salts display catalytic property in the conversion of aldoximes into nitriles and cupric acetate exhibits much higher activity than other catalysts. The corresponding amide was detected in almost all cases and acetonitrile was found to be involved in the conversion of aldoximes into nitriles.

NHC-catalyzed silylative dehydration of primary amides to nitriles at room temperature

Ahmed, Jasimuddin,Hota, Pradip Kumar,Maji, Subir,Mandal, Swadhin K.,Rajendran, N. M.

, p. 575 - 578 (2020)

Herein we report an abnormal N-heterocyclic carbene catalyzed dehydration of primary amides in the presence of a silane. This process bypasses the energy demanding 1,2-siloxane elimination step usually required for metal/silane catalyzed reactions. A detailed mechanistic cycle of this process has been proposed based on experimental evidence along with computational study.

Tetrachloropyridine: A new reagent for the dehydration of aldoximes under microwave

Lingaiah, Nagarapu,Narender, Ravirala

, p. 2391 - 2394 (2002)

Dehydration of aldoximes to nitriles using tetrachloropyridine under microwave in dry media is described. The procedure is applicable to a variety of aldoximes and the reagent can be recycled and reused.

Polyethylene glycol supported phosphorus chloride: An efficient and recyclable catalyst for the preparation of nitriles from aldoximes

Zhang, Xiao-Lan,Sheng, Shou-Ri,Wei, Mei-Hong,Liu, Xiao-Ling

, p. 513 - 517 (2017)

Polyethylene glycol (PEG) supported phosphorus chloride has been developed and used as an efficient and recyclable catalyst for dehydration of various aldoximes into the corresponding nitriles. This protocol has many advantages such as high conversion, high selectivity, short reaction time, mild reaction conditions, and simple experimental procedure.

Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines

Tnay, Ya Lin,Ang, Gim Yean,Chiba, Shunsuke

, p. 1933 - 1943 (2015)

We report herein studies on copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines. Treatment of N-H ketimines having an α-sp3 hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C-C bond cleavage to give the corresponding carbonitrile and carbon radical intermediate. This radical process has been applied for the construction of oxaspirocyclohexadienones as well as in the electrophilic cyanation of Grignard reagents with pivalonitrile as a CN source.

Supported monomeric vanadium catalyst for dehydration of amides to form nitriles

Sueoka, Shoichiro,Mitsudome, Takato,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi

, p. 8243 - 8245 (2010)

Monomeric vanadium oxide species is created on the surface of hydrotalcite (V/HT), which acts as a reusable solid catalyst for the highly efficient dehydration of amides into the corresponding nitriles.

Copper-catalyzed cyanation of aryl iodides using nitromethane

Ogiwara, Yohei,Morishita, Hiromitsu,Sasaki, Minoru,Imai, Hiroki,Sakai, Norio

, p. 1736 - 1739 (2017)

The copper-catalyzed cyanation of aryl iodides is described using nitromethane as a CN source. In situ generation of a “CN” species from nitromethane is plausible. This strategy is an advantageous synthetic method for the construction of an aromatic CCN bond, because nitromethane is a common and easily handled compound that is readily available as a cyanation reagent, and its use allows the avoidance of using toxic metal cyanides.

Copper-catalyzed cyanation of heteroaryl bromides: A novel and versatile catalyst system inspired by nature

Schareina, Thomas,Zapf, Alexander,M?gerlein, Wolfgang,Müller, Nikolaus,Beller, Matthias

, p. 555 - 558 (2007)

An improved copper catalyst system for the cyanation of heteroaryl halides leading to substituted heteroaryl nitriles is described. The catalyst system consists of simple CuI and N-alkylimidazoles, and mimics known Cu-containing metalloproteins. It is stable, commercially available, cheap and easily tunable. By using inexpensive and non-toxic K4[Fe(CN)6] and the novel Cu catalysts we were able to cyanate both activated and non-activated heteroarenes with high yield and selectivity. The generality of the procedure is demonstrated by a variety of different examples, some of which did not react under other known methods. Georg Thieme Verlag Stuttgart.

Ultrasound-promoted synthesis of nitriles from aldoximes under ambient conditions

Jiang, Nan,Ragauskas, Arthur J.

, p. 4479 - 4481 (2010)

Copper(II) acetate proves to be an active catalyst for ultrasound-promoted conversion of aldoximes into nitriles. This dehydration reaction was carried out in acetonitrile under ambient conditions to provide nitriles with moderate tolerance toward water, which allows one-pot synthesis of a nitrile from an aldehyde with minimal purification.

High-throughput synthesis of symmetrically 3,5-disubstituted 4-amino-1,2,4-triazoles from aldehydes using microwave

Koshima, Hideko,Hamada, Mitsuo,Tani, Makiko,Iwasaki, Shunsuke,Sato, Fumika

, p. 2145 - 2148 (2002)

Symmetrically 3,5-substituted 4-amino-1,2,4-triazoles are quickly prepared from aromatic aldehydes via nitriles by two-step reactions without any separation under microwave irradiation for each several minutes.

Efficient dehydration of primary amides to nitriles catalyzed by phosphorus-chalcogen chelated iron hydrides

Li, Kai,Sun, Hongjian,Yang, Wenjing,Wang, Yajie,Xie, Shangqing,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter

, (2020)

A series of phosphorus-chalcogen chelated hydrido iron (II) complexes 1–7, (o-(R'2P)-p-R-C6H4Y)FeH (PMe3)3 (1: R = H, R' = Ph, Y = O; 2: R = Me, R' = Ph, Y = O; 3: R = H, R' = iPr, Y = O; 4: R = Me, R' = iPr, Y = O; 5: R = H, R' = Ph, Y = S; 6: R = Me, R' = Ph, Y = S; 7: R = H, R' = Ph, Y = Se), were synthesized. The catalytic performances of 1–7 for dehydration of amides to nitriles were explored by comparing three factors: (1) different chalcogen coordination atoms Y; (2) R' group of the phosphine moiety; (3) R substituent group at the phenyl ring. It is confirmed that 5 with S as coordination atom has the best catalytic activity and 7 with Se as coordination atom has the poorest catalytic activity among complexes 1, 5 and 7. Electron-rich complex 4 is the best catalyst among the seven complexes and the dehydration reaction was completed by using 2 mol% catalyst loading at 60 °C with 24 hr in the presence of (EtO)3SiH in THF. Catalyst 4 has good tolerance to many functional groups. Among the seven iron complexes, new complexes 3 and 4 were obtained via the O-H bond activation of the preligands o-iPr2P(C6H4)OH and o-iPr2P-p-Me-(C6H4)OH by Fe(PMe3)4. Both 3 and 4 were characterized by spectroscopic methods and X-ray diffraction analysis. The catalytic mechanism was experimentally studied and also proposed.

Straightforward uranium-catalyzed dehydration of primary amides to nitriles

Enthaler, Stephan

, p. 9316 - 9319 (2011)

Easy for U! The efficient uranium-catalyzed dehydration of a variety of primary amides, using N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA) as a dehydration reagent, to the corresponding nitriles has been investigated. With this catalyst system, extraordinary catalyst activities and selectivities were feasible (see scheme; DME=dimethoxyethane). Copyright

An efficient approach to the ammoxidation of alcohols to nitriles and the aerobic oxidation of alcohols to aldehydes in water using Cu(ii)/pypzacac complexes as catalysts

Xie, Jing-Bo,Bao, Jia-Jing,Li, Hong-Xi,Tan, Da-Wei,Li, Hai-Yan,Lang, Jian-Ping

, p. 54007 - 54017 (2014)

Reactions of 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)acetic acid (pypzacacH) ligand with Cu(OAc)2, Cu(NO3)2, CuSO4, Cu(ClO4)2 or CuCl2 produced four dinuclear Cu(ii) complexes [{(MeOH)Cu(OAc)}(μ-κ2:κ1-pypzacac)]2·0.5H2O (1·0.5H2O), [{Cu(pypzacac)}(μ-κ2:κ1-pypzacac)2{Cu(H2O)2}](NO3)·2(MeOH)0.5·6H2O (2·2(MeOH)0.5·6H2O), [{(MeOH)Cu(mpypzacac)}(μ-SO4)]2·2MeOH (3·2MeOH; mpypzacac = methyl 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)acetate), [{Cu(mpypzacac)2}(μ-κ2:κ1-pypzacac){Cu(mpypzacac)}](ClO4)3·MeOH (4·MeOH) and one polymeric Cu(ii) complex [(CuCl)(μ-κ3:κ1-pypzacac)]n (5), respectively. The mpypzacac ligand in 3 and 4 was in situ generated via the Cu2+-catalyzed dehydrative esterification of acetic acid of the pypzacacH ligand. Complexes 1-5 are characterized by elemental analysis, IR and single-crystal X-ray diffraction. Complex 1 contains two {(MeOH)Cu(OAc)} fragments that are interconnected by two μ-κ2:κ1-pypzacac- ligands, forming a dimeric structure. In 2, {Cu(pypzacac)} and {Cu(H2O)2} units are bridged by a pair of μ-κ2:κ1-pypzacac- ligands. In 3, two {Cu(mpypzacac)} fragments are linked by two μ-κ1:κ1-SO42- ions to form a dinuclear structure. Complex 4 also adopts a dimeric structure in which {Cu(mpypzacac)2} and {Cu(mpypzacac)} units are interconnected by one μ-κ3:κ1-pypzacac- ligand. Complex 5 contains a 1D chain in which (CuCl) fragments are interlinked by μ-κ3:κ1-pypzacac- ligands. Complexes 1-5 exhibited excellent catalytic performance in the ammoxidation of alcohol to nitrile and the aerobic oxidation of alcohol to aldehyde in water. The catalytic aqueous solution was easily separated and could be reused for several cycles without any obvious decay of catalytic efficiency.

Metal-free dehydrosulfurization of thioamides to nitriles under visible light

Xu, Tianxiao,Cao, Tianpeng,Feng, Qingyuan,Huang, Shenlin,Liao, Saihu

, p. 5151 - 5153 (2020)

A visible light-mediated, metal-free dehydrosulfurization reaction of thioamides to nitriles is described. This reaction features high yields, mild reaction conditions, and the use of a cheap organic dye as the photoredox catalyst and air as the oxidant.

Direct oxidative conversion of alkyl halides into nitriles with molecular iodine in aqueous ammonia

Iida, Shinpei,Togo, Hideo

, p. 1639 - 1642 (2008)

The direct oxidative conversion of various benzylic alkyl halides and primary alkyl halides into corresponding nitriles was efficiently and simply carried out using molecular iodine in aqueous ammonia. This novel reaction converts alkyl halides into corresponding nitriles without changing the number of carbon atoms. Thieme Stuttgart.

Dehydration of aldoximes to nitriles using trichloroacetonitrile without catalyst

Ma, Xiaoyun,Liu, Dan,Chen, Zhengjian

, p. 3261 - 3266 (2021/06/30)

Trichloroacetonitrile has been found to be an efficient dehydrating agent for a range of aldoximes including aromatic and heterocyclic aldoxime yielding the corresponding nitriles in moderate to good yields. The dehydration reactions can take place in non-acetonitrile media without the aid of a metal catalyst. In addition, it has been confirmed that trichloroacetonitrile was converted into trichloroacetamide in the reaction.

A new reagent for efficient synthesis of nitriles from aldoximes using methoxymethyl bromide

ULUDAG, Nesimi,GIDEN, Ozge NUR

, p. 993 - 998 (2021/02/05)

This study outlines an efficient, high-yielding, and rapid method by which to access diverse nitriles from aldoximes with methoxymethyl bromide (MOM-Br) in THF. It represents the first application of MOM-Br as a deoximation reagent to synthesize nitriles. The reaction was performed at reflux to ensure excellent yield (79-96%) of the nitriles within 20-45 minutes. Furthermore, this method has been successfully applied to the synthesis of the synthesis precursor of aromatic, heteroaromatic, cyclic, and acyclic aliphatic.

Method for dehydrating primary amide into nitriles under catalysis of cobalt

-

Paragraph 0084-0086, (2021/06/21)

The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.

Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide

Cai, Mingzhong,Huang, Bin,Liu, Rong,Xu, Caifeng

, (2021/12/03)

Pd(OAc)2/XPhos–SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly efficient catalyst for the cyanation of aryl chlorides with potassium ferrocyanide. The reaction proceeded smoothly at 100 or 120?oC with K2CO3 or KOAc as base, delivering a variety of aromatic nitriles in good to excellent yields. The isolation of the crude products is facilely performed by extraction with cyclohexane and more importantly, both expensive Pd(OAc)2 and XPhos–SO3Na in PEG-400/H2O system could be easily recycled and reused at least six times without any apparent loss of catalytic efficiency. Graphical Abstract: Palladium-catalyzed cyanation of aryl chlorides with potassium ferrocyanide leading to aryl nitriles by using Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O as a highly efficient and recyclable catalytic system is described.[Figure not available: see fulltext.]

Process route upstream and downstream products

Process route

diethyl ether
60-29-7,927820-24-4

diethyl ether

bromocyane
506-68-3

bromocyane

[2]thienyl magnesium <sup>(1+)</sup>; bromide

[2]thienyl magnesium (1+); bromide

2-bromothiophene
1003-09-4

2-bromothiophene

thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

Conditions
Conditions Yield
thiophene-2-carbaldehyde oxime
38266-87-4

thiophene-2-carbaldehyde oxime

thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

Conditions
Conditions Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 4 A molecular sieve; In acetonitrile; at 80 ℃; for 0.166667h;
95%
for 0.0333333h; Irradiation;
88%
With aluminum oxide; methanesulfonyl chloride; at 100 ℃; for 0.133333h;
85%
With 2,2'-oxalyldi(o-sulfobenzimide); In acetonitrile; 1) r.t., 15 min, 2) reflux, 30 min;
83%
With 1,1'-oxalyldiimidazole; In benzene; 15 min, r.t; 65-70 degC, 5 min;
80%
With trichloromethyl chloroformate; In acetonitrile; for 0.0833333h;
77%
With N,N-dimethyl-formamide; at 135 ℃; for 48h;
75%
Montmorillonite KSF; In toluene; for 19h; Heating;
65%
With sulfuric acid; silica gel; for 0.0833333h; Irradiation;
64%
With sodium carbonate;
diethyl ether
60-29-7,927820-24-4

diethyl ether

[2]thienyl magnesium <sup>(1+)</sup>; bromide

[2]thienyl magnesium (1+); bromide

cyanogen chloride
506-77-4

cyanogen chloride

2-bromothiophene
1003-09-4

2-bromothiophene

thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

Conditions
Conditions Yield
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

Conditions
Conditions Yield
With trimethylsilylacetylene; zinc(II) chloride; In chloroform; for 4h; Heating;
100%
With ammonium hydroxide; sodium persulfate; sodium iodide; iron(II) chloride; In 1,2-dichloro-ethane; at 20 - 50 ℃; for 16h;
98%
With trifluorormethanesulfonic acid; trimethylsilylazide; In acetonitrile; at 25 ℃; for 0.00138889h; Flow reactor;
98%
With ammonia; iodine; In tetrahydrofuran; water; at 20 ℃; for 0.0833333h;
97%
With trifluorormethanesulfonic acid; O-benzenesulfonyl-acetohydroxamic acid ethyl ester; In dichloromethane; at 23 ℃; for 24h; Inert atmosphere;
97%
With bismuth(lll) trifluoromethanesulfonate; acetylhydroxamic acid; In acetonitrile; for 15h; Reflux;
94%
With ammonia; oxygen; In ethanol; water; for 1.5h; Reflux;
93%
With hydroxylamine hydrochloride; In 1-methyl-pyrrolidin-2-one; for 0.0833333h; Heating;
92%
With ammonium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In acetonitrile; at 20 ℃; for 2h;
92%
thiophene-2-carbaldehyde; With hydroxylamine hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 0.0833333h;
With potassium hydrogen difluoride; 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate; In water; at 20 ℃; for 3h;
92%
With oxygen; copper; ammonium chloride; In pyridine; 1.) 20 deg C, 15 h, 2.) 60 deg C, 24 h;
91%
With hydroxylamine hydrochloride; In various solvent(s); at 110 - 115 ℃; for 4h;
90%
With aluminum oxide; hydroxylamine hydrochloride; di(n-butyl)tin oxide; for 0.05h; microwave irradiation;
90%
With hydroxylamine hydrochloride; pyrographite; methanesulfonyl chloride; at 100 ℃; for 2h;
90%
With trichloroisocyanuric acid; ammonia; In water; at 20 - 60 ℃;
90%
With sodium azide; trichlorophosphate; at 20 ℃; for 0.0166667h; Inert atmosphere;
89%
With Nitroethane; pyridine hydrochloride; for 1h; Heating;
88%
With hydroxylamine hydrochloride; In glycerol; at 90 ℃; for 7h; Green chemistry;
86%
With aluminum oxide; hydroxylamine hydrochloride; methanesulfonyl chloride; at 100 ℃; for 0.5h;
85%
With carbon tetrabromide; hydroxylamine hydrochloride; triethylamine; 1-butyl-2,3-dimethylimidazolium diphenyl(3-sulfonatophenyl)phosphine; In acetonitrile; at 20 ℃;
85%
With hydroxylamine hydrochloride; In N,N-dimethyl-formamide; at 120 ℃; for 2h; Green chemistry;
85%
With ferric(III) bromide; trimethylsilylazide; In acetonitrile; at 60 ℃; for 4h;
85%
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine; In dichloromethane; at 20 ℃; for 40h;
84%
With ammonium hydroxide; dihydrogen peroxide; at 100 ℃; for 4h; Green chemistry;
84%
With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride; at 100 ℃; for 0.25h; microwave irradiation;
80%
With hexamethylene bis(N-methylimidazolium)bis(dichloroiodate); ammonia; In water; acetonitrile; at 20 ℃; for 4.5h;
80%
With pyridine; hydroxylamine hydrochloride; 1.) 10 min, 2.) toluene, 3 h, reflux;
78%
With tin(II) chloride dihdyrate; hydroxylamine hydrochloride; sodium hydrogencarbonate; In acetonitrile; at 80 ℃; for 36h;
78%
With [2,2]bipyridinyl; 4-sulfantooxy-2,2,6,6-tetramethylpiperidinyloxy; ammonia; copper(II) bis(trifluoromethanesulfonate); sodium hydroxide; In water; acetonitrile; at 40 ℃; for 16h;
76%
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; ammonium acetate; oxygen; nitric acid; acetic acid; sodium nitrite; at 50 ℃; for 12h;
73%
thiophene-2-carbaldehyde; With hydroxylamine hydrochloride; triethylamine; In acetonitrile; for 2h; Heating;
With oxalyl dichloride; In acetonitrile; for 0.25h; Heating;
65%
With ammonium acetate; acetic acid; N-(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)acetamide tetrafluoroborate; at 70 ℃; for 12h; Inert atmosphere;
51%
With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride; at 200 ℃; for 0.05h; microwave irradiation;
47%
With ammonium hydroxide; iodine; In tetrahydrofuran; at 25 ℃; for 1h;
Multi-step reaction with 2 steps
1: pyridine; ethanol; hydroxylamine hydrochloride
2: acetic acid anhydride
With pyridine; ethanol; hydroxylamine hydrochloride; acetic anhydride;
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride / dimethyl sulfoxide / 0.33 h / 20 °C
2: dimethyl sulfoxide / 2 h / 100 °C
With hydroxylamine hydrochloride; In dimethyl sulfoxide;
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; trimethylsilylazide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; at 20 - 50 ℃; for 3h; Sonication;
100 %Chromat.
thiophene-2-carbaldehyde; With hydroxylamine hydrochloride; sodium acetate trihydrate; In ethanol; water;
With acetic anhydride; In ethanol; water; 1,2-dichloro-ethane;
With tetrafluoroboric acid diethyl ether; sodium azide; acetic acid; at 20 ℃; for 1h;
Multi-step reaction with 2 steps
1: sodium hydroxide; hydroxylamine hydrochloride / ethanol / 20 °C
2: MIL-100 (Fe)-NH4F / o-xylene / 6 h / 153 - 160 °C / Dean-Stark; Inert atmosphere
With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; o-xylene;
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride
2: poly(ethylene glycol)–bound sulfonyl chloride / dichloromethane / 0.83 h / Reflux
With hydroxylamine hydrochloride; In dichloromethane;
With ammonium hydroxide; iodine; In tetrahydrofuran; methanol; at 20 ℃;
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; pyridine / dichloromethane / 24 h / 20 °C
2: oxalyl dichloride; triethylamine / acetonitrile; dimethyl sulfoxide / 1 h / 20 °C
With pyridine; oxalyl dichloride; hydroxylamine hydrochloride; triethylamine; In dichloromethane; dimethyl sulfoxide; acetonitrile; 2: |Swern Oxidation;
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; sodium carbonate / dimethyl sulfoxide / 20 °C
2: sodium carbonate; fluorosulfonyl fluoride / dimethyl sulfoxide / 12 h / 20 °C
With fluorosulfonyl fluoride; hydroxylamine hydrochloride; sodium carbonate; In dimethyl sulfoxide;
With N-(4-sulphonic acid)butylpyridinium hydrogen sulphate; hydroxylamine 1-sulfobutylpyridine hydrosulfate salt; In para-xylene; at 120 ℃; for 2h; Green chemistry;
98.1 %Chromat.
Multi-step reaction with 2 steps
1: sodium acetate; hydroxylamine hydrochloride / water; ethanol / Reflux
2: Tropone; oxalyl dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.25 h / 50 °C / Schlenk technique; Inert atmosphere
With oxalyl dichloride; Tropone; hydroxylamine hydrochloride; sodium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; water; acetonitrile;
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; sodium carbonate / methanol; water / Reflux
2: fluorosulfonyl fluoride; triethylamine / acetonitrile / 0.25 h / 20 °C / Schlenk technique
With fluorosulfonyl fluoride; hydroxylamine hydrochloride; sodium carbonate; triethylamine; In methanol; water; acetonitrile;
thiophene-2-carbaldehyde; With hydroxylamine hydrochloride; sodium carbonate; In ethanol; water; at 20 ℃; for 4h; Green chemistry;
With triethylamine; trifluoroacetyl chloride; at 0 - 5 ℃; for 1h; Green chemistry;
1.04 g
2-thiophenylcarboxamide
5813-89-8

2-thiophenylcarboxamide

thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

Conditions
Conditions Yield
With iron(II) chloride tetrahydrate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; In tetrahydrofuran; at 70 ℃; for 2h;
89%
With oxalyl dichloride; triethylamine; In dimethyl sulfoxide; acetonitrile; at 20 ℃; for 0.666667h;
89%
With triethylamine; trifluoroacetyl chloride; In dichloromethane;
88%
With oxalyl dichloride; triethylamine; Triphenylphosphine oxide; In acetonitrile; at 20 ℃; for 0.166667h;
88%
With vanadium oxide on hydrotalcite (V/HT); In 1,3,5-trimethyl-benzene; for 72h; Reflux;
86%
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 6h;
84%
With uranyl nirate hexahydrate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; In 1,2-dimethoxyethane; at 100 ℃; for 24h;
84%
With C20H25Cl2CoN3; sodium triethylborohydride; In toluene; at 60 ℃; for 18h; Inert atmosphere;
83%
With 3 A molecular sieve; at 180 - 500 ℃; under 0.005 Torr; Pyrolysis;
82%
With Triethoxysilane; C43H50FeP4Si; zinc dibromide; In tetrahydrofuran; at 40 ℃; for 30h; Schlenk technique;
78%
With trichloromethyl chloroformate; In various solvent(s); 0-5 deg C then heated to 60 deg C, 5 min;
77%
With pyridine; <(chlorosulfinyloxy)methylene>dimethylammonium chloride; In dichloromethane; for 5h; Ambient temperature;
72%
With bis(trichloromethyl) carbonate; triethylamine; In chloroform; at 50 ℃; for 2h;
67%
With triethyl borane; phenylsilane; potassium acetate; In tetrahydrofuran; tert-butyl methyl ether; at 20 ℃; for 48h; chemoselective reaction; Inert atmosphere; Schlenk technique; Sealed tube;
59%
With triethyl borane; phenylsilane; potassium acetate; In tetrahydrofuran; tert-butyl methyl ether; at 20 ℃; for 48h; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;
59%
2-thiophenylcarboxamide; With C39H45N2; In acetonitrile; at 20 ℃; Schlenk technique; Glovebox; Inert atmosphere;
With phenylsilane; In acetonitrile; at 20 ℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;
55%
With sieve-supported lead catalyst; at 220 ℃; for 0.3h; under 2250.23 Torr;
thiophene-2-carboxaldehyde dimethylhydrazone
69819-67-6

thiophene-2-carboxaldehyde dimethylhydrazone

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

1,3,5-tris-(methoxycarbonyl)benzene
2672-58-4

1,3,5-tris-(methoxycarbonyl)benzene

2-(2-thienyl)-3,5-dimethoxycarbonylpyridine
132660-18-5

2-(2-thienyl)-3,5-dimethoxycarbonylpyridine

Conditions
Conditions Yield
In dichloromethane; at 150 ℃; for 360h;
20%
14%
16%
propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

1,3,5-tris-(methoxycarbonyl)benzene
2672-58-4

1,3,5-tris-(methoxycarbonyl)benzene

2-(2-thienyl)-3,5-dimethoxycarbonylpyridine
132660-18-5

2-(2-thienyl)-3,5-dimethoxycarbonylpyridine

Conditions
Conditions Yield
With 2-thiophenecarboxaldehyde N,N-dimethylhydrazone; In dichloromethane; at 150 ℃; for 360h;
20%
16%
14%
2-thiophenemethanol
636-72-6

2-thiophenemethanol

thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

Conditions
Conditions Yield
2-thiophenemethanol; With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
With ammonia; iodine; In dichloromethane; water; at 20 ℃; for 3h; Inert atmosphere;
99%
With copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonium hydroxide; at 100 ℃; for 24h;
96%
With ammonia; oxygen; In ethanol; water; for 3h; Reflux;
91%
With ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In water; for 24h; Reflux; Green chemistry;
90%
With ammonium hydroxide; oxygen; at 90 ℃; for 6h;
90%
With ammonium hydroxide; dihydrogen peroxide; In water; acetonitrile; at 30 ℃; for 3h;
87%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonium acetate; oxygen; nitric acid; acetic acid; at 50 ℃; for 12h; under 760.051 Torr; Sealed tube;
86%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; ammonium acetate; In water; acetonitrile; at 20 ℃; for 9h;
84%
With ammonium hydroxide; oxygen; In tert-Amyl alcohol; at 130 ℃; for 48h; under 3750.38 Torr;
81%
With 1,4-diaza-bicyclo[2.2.2]octane; TEMPOL; ammonia; copper(l) chloride; In water; acetonitrile; at 20 ℃; for 24h;
73%
With ammonium hydroxide; iodine; at 60 ℃; for 3h;
67%
With ammonium hydroxide; iodine; at 60 ℃; for 3h;
67%
With ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [{(MeOH)Cu(OAc)}(μ-k2:k1-2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)acetic acid(-H))]2*0.5H2O; tetraethylammonium iodide; oxygen; potassium carbonate; In water; at 60 ℃; for 24h; under 760.051 Torr;
41%
With manganese(IV) oxide; ammonia; oxygen; In toluene; at 100 ℃; for 2h; under 10126 Torr; Autoclave;
89 %Chromat.
With ammonium hydroxide; oxygen; In tert-Amyl alcohol; at 130 ℃; for 18h; under 3750.38 Torr;
88 %Chromat.
With ammonium hydroxide; oxygen; In tert-Amyl alcohol; at 130 ℃; for 24h; under 3750.38 Torr; Sealed tube; Autoclave;
75 %Chromat.
Ethyl thiophene-2-carboxylate
2810-04-0

Ethyl thiophene-2-carboxylate

thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

Conditions
Conditions Yield
Ethyl thiophene-2-carboxylate; With sodium diisobutyl-tert-butoxyaluminium hydride; In tetrahydrofuran; at 0 ℃; for 4h; Inert atmosphere;
With ammonia; iodine; In tetrahydrofuran; water; at 0 - 20 ℃; for 3h;
72%
Multi-step reaction with 2 steps
1: tetrahydrofuran / 65 °C
2: 160 °C
In tetrahydrofuran;
2-bromothiophene
1003-09-4

2-bromothiophene

thiophene-2-carbonitrile
1003-31-2

thiophene-2-carbonitrile

Conditions
Conditions Yield
2-bromothiophene; With magnesium; In tetrahydrofuran; at 20 ℃; for 2h;
With N,N-dimethyl-formamide; In tetrahydrofuran; at 0 ℃; for 2h;
With ammonia; iodine; In tetrahydrofuran; water; at 20 ℃; for 2h;
70%
With NaCN; sodium chloride; CuCN; In water;
63%

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  • Main Products:56
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  • BAYNOE CHEM CO.,LTD
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  • Main Products:4
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