51220-00-9

Usage

Physical state

liquid

Color

colorless to pale yellow

Odor

sharp, fruity

Primary use

intermediate in production of pharmaceuticals and agrochemicals

Other uses

raw material for synthesis of various organic compounds

Hazards

harmful if ingested or inhaled, can cause skin and eye irritation

Safety precautions

handle with care, use appropriate safety measures when working with it

Upstream product

• 10487-66-8 3-(2-chloro-phenyl)-2-cyano-acrylic acid 
• 141692-07-1 α-benzenesulfonyl-2-chloro-ξ-cinnamonitrile 
• 89-98-5 2-chloro-benzaldehyde 
• 793706-87-3 (1,1-dimethylethoxy)diphenylsilylacetonitrile 
• 3252-43-5 dibromoacetonitrile 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 4336-70-3 (cyanomethyl)triphenylphosphonium chloride 
• 873-31-4 2-chlorophenylacetylene 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 24166-09-4 (cyanomethyl)triphenylarsonium bromide 
• 107-13-1 acrylonitrile 
• 108-90-7 chlorobenzene 
• 333309-74-3 (E)-1-(2'-chlorophenyl)-2-bromoethylene 
• 433231-64-2 C₂₀H₁₀F₁₂NO₂P 

Downstream Products

• 7315-17-5 3-(2-chloro-phenyl)-propionitrile 
• 74738-15-1 4-(2-chlorophenyl)-1H-pyrrole-3-carbonitrile 
• 1794-45-2 (E)-3-(2-chlorophenyl)propenal 
• 51219-99-9 (Z)-3-(2-chlorophenyl)propenenitrile 
• 1392592-80-1 S-1-(2-chlorophenyl)-2-cyanoethyl thioacetate 
• 1392592-76-5 3-amino-1-(2-chlorophenyl)propane-1-sulfonic acid 

Relevant academic research and scientific papers

An environmentally benign procedure for the synthesis of aryl and arylvinyl nitriles assisted by microwave in ionic liquid

Aryl and arylvinyl nitriles have been prepared in good yields from the corresponding bromides with potassium hexacyanoferrate (II) using palladium-catalyzed reactions in ionic liquid under microwave irradiation. Georg Thieme Verlag Stuttgart.

One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts

A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O 2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO 2 Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.

PROCESS FOR HYDROCYANATION OF TERMINAL ALKYNES

The present invention refers to a process for a Rh-catalyzed Anti-Markovnikov hydrocyanation of terminal alkynes which process discloses, for the first time, the highly stereo- and regio-selective hydrocyanation of terminal alkynes to furnish E- configured alkenyl nitriles and the catalyst used in the present process.

Rh-Catalyzed Anti-Markovnikov Hydrocyanation of Terminal Alkynes

We report the first highly stereo- and regioselective hydrocyanation of terminal alkynes to furnish E-configured alkenyl nitriles. Acrylonitriles can be accessed on gram scale with broad substrate scope and functional group tolerance. The hydrocyanation reaction employs acetone cyanohydrin as a practical alternative to HCN gas.

Synthesis of olefins via a Wittig reaction mediated by triphenylarsine

An arsine-mediated Wittig reaction for the synthesis of olefins is described. After heating triphenylarsine in the presence of an activated alkyl bromide for 30?min, the resulting arsonium salt condensed with aldehydes in as little as 5?min at room temperature, yielding the olefins in high yields. Aromatic, heteroaromatic, and alkyl aldehydes were all suitable substrates for this process.

Wittig Olefination Using Phosphonium Tetraphenylborate in the Absence of Additional Base

The thermal decomposition of (substituted methyl)triphenylphosphonium tetraphenylborates, which can also be generated in situ from the corresponding phosphonium halide and NaBPh4, with an aldehyde affords olefins in 22-100% yields. This Wittig olefination does not need use additional base to form phosphorus ylide, and is highly tolerant of benzoic acid.

Direct oxidative coupling of benzenes with acrylonitriles to cinnamonitriles catalyzed by Pd(OAc)2/HPMoV/O2 system

A facile direct synthesis of cinnamonitriles from acrylonitriles and benzenes is successfully achieved by using Pd(OAc)2/HPMoV/O 2 catalyst system via the direct C-H bond activation of benzenes using molecular oxygen as a terminal oxidant.

Indium(I) bromide-mediated coupling of dibromoacetonitrile with aldehydes followed by Boord elimination of bromine and oxygen of β-bromo alkoxides for preparation of 3-organyl-2-alkenenitriles

The organoindium compound derived from indium monobromide and dibromoacetonitrile reacts with carbonyl compounds to afford the corresponding 2-bromo-2-cyano-indium(III) alkoxide. The action of a second equivalent of indium monobromide onto the alkoxides derived from aldehydes promotes the Boord elimination of the β-related oxygen and bromine atoms leading to 2-alkenenitriles.

Highly (Z)-selective synthesis of β-monosubstituted α,β-unsaturated cyanides using the peterson reaction

(Chemical Equation Presented) The Peterson reaction between (t-BuO)Ph 2SiCH2CN and various aldehydes furnishes the corresponding β-monosubstituted α,β-unsaturated cyanides with high Z selectivity (Z:E = 92:8 to >98:2).

Highly Z-selective synthesis of disubstituted α, β-unsaturated cyanides and amides using 10-P-5 wittig type reagents

Phosphoranes (10-P-5) bearing cyanomethyl, acetamide, and N, N-dimethylacetamide groups were examined for Wittig type reactions. All three reacted to give the corresponding olefins. The reaction of the cyanomethyl reagent with aldehydes gave α, β-unsatura