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

Description

2-BROMOPROPIONITRILE, also known as 2-bromo-2-propenenitrile, is an organic compound with the chemical formula C3H4BrN. It is a colorless to pale yellow liquid with a sharp, unpleasant odor. 2-BROMOPROPIONITRILE is characterized by its reactivity and is commonly used as a chemical intermediate in various industrial applications.

Uses

Used in Polymer Industry:
2-BROMOPROPIONITRILE is used as an initiator for [atom transfer radical polymerization (AGET ATRP)] for [the synthesis of polymers with controlled molecular weight and architecture]. In this process, 2-BROMOPROPIONITRILE initiates the polymerization of acrylonitrile, which is catalyzed by Yb-based catalysts. This allows for the production of polymers with specific properties, such as improved strength, flexibility, and thermal stability.
The use of 2-BROMOPROPIONITRILE in AGET ATRP enables the synthesis of a wide range of polymers with tailored characteristics, making it a valuable tool in the development of new materials for various applications, including automotive, electronics, and packaging industries.

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

Upstream product

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

Downstream Products

• 7178-92-9 1-Hydroxy-α-methylcyclohexaneacetonitrile 
• 29478-57-7 3-hydroxy-3-phenyl-2-methylpropionitrile 
• 7391-29-9 2-methyl-3-oxo-3-phenylpropanenitrile 
• 53094-22-7 3-amino-2-methyl-3-phenyl-acrylonitrile 
• 38010-61-6 2-(2-Cyano-2-methyl-1-phenyl-ethyl)-malonic acid diethyl ester 
• 105041-69-8 3-Hydroxy-2-methyl-3-phenylbutanenitrile 
• 4468-47-7 2-methyl-3-oxo-butyronitrile 
• 3764-02-1 2-methyl-3-oxo-pentanenitrile 
• 29668-61-9 diethyl (1-cyanoethyl)phosphonate 
• 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 
• 43055-42-1 (Cyano-methyl-methyl)-triphenyl-phosphonium; bromide 
• 96234-71-8 2-(2-allylphenoxy)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.

Nickel-catalyzed direct alkylation of heterocycles with α-bromo carbonyl compounds: C3-selective functionalization of 2-pyridones

Nickel HAS it: A Ni(cod)2/dppp catalyst system promotes the direct alkylation of electron-rich heterocycles with α-bromo carbonyl compounds and involves an alkyl radical intermediate (see scheme; cod=1,5-cyclooctadiene, dppp=1,3-bis(diphenylphosphino)propane). This homolytic radical aromatic substitution (HAS)-type reaction enables the C3-selective direct functionalization of 2-pyridones. Copyright

SNTHESIS AND "ANOMERIZATION" OF C-GLYCOSYL COMPUNDS RELATED TO SOME HETEROCYCLIC NATURAL PRODUCTS

Reaction of 2,3-O-isopropylidene-D-ribofuranose (13) with the stabilized Wittig reagents Ph3P=C(Me)CO2Me (14) and Ph3P=C(Me)CN (15) gave olefinic products which, upon treatment with dilute base, afforded the corresponding anhydro sugars having the β-D-anomer configuration excusively.Treatment of these kinetic products with a strong base did not affect the ester obtained from 14, but the nitrile from 15 gave a β-to-α-anomer ratio at equilibrium of 4:1.Reaction of 13 with Ph3P=CHCOMe led directly to a 7:3 mixture of β- and α-D anomers, and this ratio was changed to 1:4 upon prolonged exposure to base.Treatment of 4,6-O-ethylidene-D-glucopyranose with the Wittig reagent Ph3P=CHCOCH2CO2Et led directly to a 1:1 mixture of the anomers of the anhydro sugar in which a β-keto ester residue is attached at the (original) anomeric center.This ratio of anomeric forms coud not be changed by treatment with base, but the ethylidene-protecting group could be removed, and the resulting tetrol tritylated at the primary position.