19481-82-4

Basic information

• Product Name: 2-BROMOPROPIONITRILE
• Synonyms: 2-BROMOPROPIONITRILE;Propanenitrile, 2-broMo-;2-broMopropanenitrile;2-BroMopropionitrile 97%
• CAS NO: 19481-82-4
• Molecular Formula: C₃H₄BrN
• Molecular Weight: 133.97
• Product Categories: C1 to C5;Cyanides/Nitriles;Nitrogen Compounds;Building Blocks;C1 to C5;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 19481-82-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 68-69 °C50 mm Hg(lit.)
• Flash Point: 137 °F
• Appearance: /
• Density: 1.55 g/mL at 25 °C(lit.)
• Vapor Pressure: 5mmHg at 25°C
• Refractive Index: n20/D 1.461(lit.)
• CAS DataBase Reference: 2-BROMOPROPIONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOPROPIONITRILE(19481-82-4)
• EPA Substance Registry System: 2-BROMOPROPIONITRILE(19481-82-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 23-26-28-36/37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 19481-82-4(Hazardous Substances Data)

Usage

Uses

2-Bromopropionitrile was used as an initiator in the atom transfer radical polymerization using activators generated by electron transfer (AGET ATRP) of acrylonitrile and the reaction was catalysed by Yb-based catalyst.

InChI:InChI=1/C3H4BrN/c1-3(4)2-5/h3H,1H3

Upstream product

• 506-68-3 bromocyane 
• 598-72-1 2-Bromopropionic acid 
• 107-12-0 propiononitrile 
• 5875-25-2 (2S)-2-bromopropanamide 
• 78-97-7 2-hydroxy-propionitrile 
• 107-13-1 acrylonitrile 
• 5875-25-2 2-bromo-propionic acid amide 

Downstream Products

• 7391-29-9 2-methyl-3-oxo-3-phenylpropanenitrile 
• 53094-22-7 3-amino-2-methyl-3-phenyl-acrylonitrile 
• 105041-69-8 3-Hydroxy-2-methyl-3-phenylbutanenitrile 
• 31787-36-7 2-(2-Cyano-1,2-dimethyl-ethyl)-malonic acid diethyl ester 
• 885959-22-8 2-Brompropionamidin 
• 24889-08-5 2-(4-Chlorophenoxy)propionitrile 
• 475159-18-3 2-(1-ethylpropylamino)-propionitrile 
• 62916-24-9 α-[3-(2'-chloro-4'-trifluoromethylphenoxy)-6-chlorophenoxy]propionitrile 
• 1140328-93-3 1,3-bis(pentafluorophenyl)but-2-en-1-one 
• 1140328-87-5 4,4,4-trifluoro-3-hydroxy-2-methyl-3-pentafluorophenylbutyronitrile 
• 1204351-47-2 2-(2-fluoro-6-formylphenoxy)propanenitrile 
• 1204351-48-3 2-(4-fluoro-2-formylphenoxy)propanenitrile 
• 1204351-46-1 2-(5-fluoro-2-formylphenoxy)propanenitrile 
• 1204351-49-4 2-(2-formyl-6-methoxyphenoxy)propanenitrile 

Relevant articles and documents

2,4,4,6-Tetrabromocyclohexa-2,5-dienone in the presence of triphenylphosphine as a specific reagent for nucleophilic substitution in cyanohydrins

A convenient method for the synthesis of α-bromonitriles from aliphatic cyanohydrins using the 2,4,4,6-tetrabromocyclohexa-2,5-dienone complex with triphenylphosphine was developed.

(2-Cyanoallyl)trimethylsilane and (2-Cyanoethyl)trimethylsilane. Unique ?? Captodative Systems

Addition reactions of (2-cyanoallyl)trimethylsilane as well as hydrogen abstraction reactions of (2-cyanoethyl)trimethylsilane were examined.These compounds exhibit high reactivities in free-radical reactions, demonstrating existence of the ?? captodative effect.

Synthesis of enantiomerically enriched-bromonitriles from amino acids

Two methods were investigated for the preparation of six chiral-bromonitriles with different optic purities. The nitrous deamination of amino acids gives-bromoacids, which react with chlorosulfonyl isocyanate followed by triethylamine to afford-bromonitriles with moderate enantiomeric excess. However, the dehydration of corresponding-bromoamids using thionyl chloride gives-bromonitriles with good enantiomeric excess up to 94%. The use of phosphoryl chloride instead of thionyl chloride results in more than 30% racemization as determined by high-performance liquid chromatograpic analysis.