Basic Info

Common NameBromobenzyl Cyanide(F04328)
2D Structure
Description

Bromobenzyl cyanide is a colorless organobromide compound. It is slightly soluble in water but readily soluble in organic solvents. Bromobenzyl cyanide is resistant to the action of water and oxidizers; it decomposes upon heating above 120° C and also when exposed to the action of a number of metals, which are thereby intensely corroded. Bromobenzyl cyanide is obtained by the action of sodium cyanide or potassium cyanide on benzyl chloride with subsequent bromination of the benzyl cyanide that has been formed. Bromobenzyl cyanide acts powerfully on the mucous membranes of the eye, causing irritation and heavy lachrymation. It was proposed as a toxic lachrymatory agent at the end of World War I and an irritant gas for law enforcement. It is chemically and biologically similar to Benzyl cyanide. Benzyl cyanide and its derivatives are used in organic synthesis for dyes, perfumes, pesticides, pharmaceuticals, especially penicillin precursors.

FRCD IDF04328
CAS Number5798-79-8
PubChem CID22044
FormulaC8H6BrN
IUPAC Name

2-bromo-2-phenylacetonitrile

InChI Key

XUHFBOUSHUEAQZ-UHFFFAOYSA-N

InChI

InChI=1S/C8H6BrN/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8H

Canonical SMILES

C1=CC=C(C=C1)C(C#N)Br

Isomeric SMILES

C1=CC=C(C=C1)C(C#N)Br

Synonyms
        
            2-bromo-2-phenylacetonitrile
        
            Bromobenzyl cyanide
        
            5798-79-8
        
            Bromo(phenyl)acetonitrile
        
            Camite
        
            Brombenzyl cyanide
        
            Bromobenzylcyanide
        
            Bromobenzylnitrile
        
            alpha-Bromophenylacetonitrile
        
            CA (Tear gas)
        
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsMonocyclic benzene moiety - Nitrile - Carbonitrile - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Organobromide - Organohalogen compound - Alkyl halide - Alkyl bromide - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Properties

Property NameProperty Value
Molecular Weight196.047
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Complexity141
Monoisotopic Mass194.968
Exact Mass194.968
XLogP2.5
Formal Charge0
Heavy Atom Count10
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1