28694-90-8

Basic information

• Product Name: 2-(4-aminophenyl)propiononitrile
• Synonyms: 2-(4-aminophenyl)propiononitrile;2-(4-Aminophenyl)propanenitrile;alpha-Methyl-4-methylphenylacetonitrile;2-(4-Aminophenyl)propionitrile;4-Amino-methylbenzeneacetonitrile;2-(4-aminophenyl)propanenitrile (en);(4-Aminophenyl)(methyl)acetonitrile;(4-Aminophenyl)(methyl)acetonitrile, 4-(1-Cyanoethyl)aniline
• CAS NO: 28694-90-8
• Molecular Formula: C₉H₁₀N₂
• Molecular Weight: 146.1891
• EINECS: 249-164-7
• Mol File: 28694-90-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 55-57°C
• Boiling Point: 306.1°Cat760mmHg
• Flash Point: 138.9°C
• Appearance: /
• Density: 1.081g/cm³
• Vapor Pressure: 0.000788mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(4-aminophenyl)propiononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-aminophenyl)propiononitrile(28694-90-8)
• EPA Substance Registry System: 2-(4-aminophenyl)propiononitrile(28694-90-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 28694-90-8(Hazardous Substances Data)

Usage

General Description

2-(4-aminophenyl)propiononitrile, also known as Propham, is an organic chemical compound primarily used in the production of pharmaceuticals and pesticides. 2-(4-aminophenyl)propiononitrile belongs to the class of organic compounds known as aniline and substituted anilines. It's composed of a benzene ring attached to an amine group and a propionitrile group. It is produced synthetically and may pose hazards such as skin and eye irritation upon exposure. Given its industrial uses, it's crucial to handle and dispose of it properly to avoid environmental contamination. Its molecular formula is C9H10N2 and it has a molar mass of 146.19 g/mol.

InChI:InChI=1/C9H10N2/c1-7(6-10)8-2-4-9(11)5-3-8/h2-5,7H,11H2,1H3

Upstream product

• 1572-99-2 ethyl 2-cyanopropionate 
• 106-40-1 4-bromo-aniline 
• 3544-25-0 p-aminophenylacetonitrile 
• 68-12-2 N,N-dimethyl-formamide 
• 50712-63-5 2-(4-nitrophenyl)-propionitrile 

Downstream Products

• 56353-52-7 2-(4'-amino-3'-nitro-phenyl)-propionic acid 
• 28694-91-9 N-[4-(cyano-methyl-methyl)-phenyl]-acetamide 
• 57555-89-2 N-[4-(cyano-methyl-methyl)-2-nitro-phenyl]-acetamide 
• 21850-61-3 2-(4-hydroxyphenyl)propanenitrile 
• 99739-16-9 2-amino-α-methyl benzothiazole-6-acetonitrile 
• 54785-32-9 2-(2-phenyl-benzooxazol-5-yl)-propylamine 
• 51234-45-8 ethyl 2-(3-amino-4-hydroxyphenyl)-propionate 
• 51234-67-4 2-[2-(4-methanesulfonyl-phenyl)-benzooxazol-5-yl]-propionic acid ethyl ester 
• 54785-41-0 2-[2-(4-methanesulfonyl-phenyl)-benzooxazol-5-yl]-propionic acid 
• 51234-64-1 2-(2-benzo[1,3]dioxol-5-yl-benzooxazol-5-yl)-propionic acid 
• 51234-34-5 2-[2-(4-chloro-2-hydroxy-phenyl)-benzooxazol-5-yl]-propionic acid 
• 51234-37-8 2-[2-(4-acetyl-phenyl)-benzooxazol-5-yl]-propionic acid 
• 54785-39-6 2-[2-(4-methoxy-phenyl)-benzooxazol-5-yl]-propionic acid 
• 51234-35-6 2-[2-(4-chloro-2-hydroxy-phenyl)-benzooxazol-5-yl]-propionitrile 

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.

Selective α-Monomethylation by an Amine-Borane/N,N-Dimethylformamide System as the Methyl Source

A new and practical α-monomethylation strategy using an amine-borane/N,N-dimethylformamide (R3N-BH3/DMF) system as the methyl source was developed. This protocol has been found to be effective in the α-monomethylation of arylacetonitriles and arylacetamides. Mechanistic studies revealed that the formyl group of DMF delivered the carbon and one hydrogen atoms of the methyl group, and R3N-BH3 donated the remaining two hydrogen atoms. Such a unique reaction pathway enabled controllable assemblies of CDH2-, CD2H-, and CD3- units using Me2NH-BH3/d7-DMF, Me3N-BD3/DMF and Me3N-BD3/d7-DMF systems, respectively. Further application of this method to the facile synthesis of anti-inflammatory flurbiprofen and its varied deuterium-labeled derivatives was demonstrated.