83901-88-6

Basic information

• Product Name: 4-Cyanomethylbenzoic acid
• Synonyms: 4-(Cyanomethyl)benzoic acid ethyl ester
• CAS NO: 83901-88-6
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Mol File: 83901-88-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 28 °C
• Boiling Point: 325.971 °C at 760 mmHg
• Flash Point: 153.252 °C
• Appearance: /
• Density: 1.112
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Cyanomethylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cyanomethylbenzoic acid(83901-88-6)
• EPA Substance Registry System: 4-Cyanomethylbenzoic acid(83901-88-6)

Safety Data

• Hazardous Substances Data: 83901-88-6(Hazardous Substances Data)

Usage

General Description

4-Cyanomethylbenzoic acid is a chemical compound that is commonly used in the manufacturing of pharmaceuticals, dyes, and other industrial applications. It is a white crystalline solid that is soluble in water and is known for its strong acidic properties. 4-Cyanomethylbenzoic acid is often used as a building block in the synthesis of various organic compounds and is considered to be a versatile and important intermediate in the production of diverse chemical products. Additionally, 4-Cyanomethylbenzoic acid is also known for its potential application as a corrosion inhibitor and as an additive in the production of plastics and coatings. Overall, it is a valuable and multifaceted chemical compound with a wide range of industrial uses.

Upstream product

• 26496-94-6 Ethyl 4-(bromomethyl)benzoate 
• 151-50-8 potassium cyanide 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 105-56-6 ethyl 2-cyanoacetate 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 1071-36-9 sodium cyanoacetate 
• 928664-98-6 4-isoxazoleboronic acid pinacol ester 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 175135-39-4 4-(cyanomethyl)phenyl 4-methylbenzenesulfonate 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 18293-53-3 2-trimethylsilylacetonitrile 

Downstream Products

• 89605-86-7 ethyl 4-<2-<<1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate 
• 77266-69-4 2-(4-carboethoxyphenyl)ethylamine 
• 898776-62-0 ethyl 4-(2-oxo-2-phenylethyl) benzoate 
• 1309580-85-5 ethyl 4-(1-cyano-1-methyl-ethyl)benzoate 
• 1126479-81-9 methyl 4-(1-cyano-3-phenylpropyl)benzoate 
• 50685-26-2 4-(cyanomethyl)benzoic acid 
• 50820-64-9 indole 6-carboxylic acid ethyl ester 
• 83895-12-9 ethyl 4-<2-<methyl>amino>-2-oxoethyl>-benzoate 
• 89605-91-4 ethyl 4-<2-<<3-phenyl-1-<2-(1-piperidinyl)phenyl>propyl>amino>-2-oxoethyl>-benzoate 
• 89605-49-2 ethyl 4-<2-<<2-phenyl-1-<2-(1-piperidinyl)phenyl>-1-(E)-ethenyl>amino>-2-oxoethyl>-benzoate 
• 89605-48-1 ethyl 4-<2-<<1-<2-octamethyleneimino-phenyl>-1-ethenyl>amino>-2-oxoethyl>-benzoate 
• 89605-90-3 ethyl 4-<2-<<2-phenyl-1-<2-(1-piperidinyl)phenyl>ethyl>amino>-2-oxoethyl>-benzoate 
• 89605-89-0 ethyl 4-<2-<<1-<2-(1-piperidinyl)phenyl>hexyl>amino>-2-oxoethyl>-benzoate 
• 89605-88-9 ethyl 4-<2-<<1-<2-(1-piperidinyl)phenyl>pentyl>amino>-2-oxoethyl>-benzoate 

Relevant articles and documents

Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides

α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.

Palladium-catalyzed cyanomethylation of aryl halides through domino Suzuki coupling-isoxazole fragmentation

A one-pot protocol for the cyanomethylation of aryl halides through a palladium-catalyzed reaction with isoxazole-4-boronic acid pinacol ester was developed. Mechanistically, the reaction proceeds through (1) Suzuki coupling, (2) base-induced fragmentation, and (3) deformylation as shown by characterization of all postulated intermediates. Under optimized conditions (PdCl2dppf, KF, DMSO/H2O, 130 °C) a broad spectrum of aryl bromides could be converted into arylacetonitriles with up to 88% yield.

An efficient catalyst for PD-catalyzed carbonylation of aryl arenesulfonates

(Chemical Equation Presented) Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered through high-throughput catalyst screening, which was the key for the successful carbonylation of various substrates. This catalyst is effective and works well for both electron-rich and electron-poor aryl arenesulfonates. Isolated yields of up to 90% were obtained for aryl p-fluorobenzenesulfonates and -tosylates.