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242489

Sigma-Aldrich

Bromoacetonitrile

97%

Synonym(s):

2-Bromoacetonitrile, Bromomethyl cyanide, Cyanomethyl bromide

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About This Item

Linear Formula:
BrCH2CN
CAS Number:
590-17-0
Molecular Weight:
119.95
Beilstein:
956569
EC Number:
209-672-1
MDL number:
MFCD00001884
UNSPSC Code:
12352100
PubChem Substance ID:
24854561
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.479 (lit.)

bp

60-62 °C/24 mmHg (lit.)

density

1.722 g/mL at 25 °C (lit.)

functional group

bromo
nitrile

SMILES string

BrCC#N

InChI

1S/C2H2BrN/c3-1-2-4/h1H2

InChI key

REXUYBKPWIPONM-UHFFFAOYSA-N

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General description

Bromoacetonitrileis an organic compound, generally used as a cyanoalkyl source. It is also used in organic synthesis as a chemical intermediate and an alkylating agent.

Application

Bromoacetonitrile was used in the synthesis of 1-cyanomethyl-1,1-dimethylhydrazinium bromide.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB1192
SDBB1191
STBL2417
STBL1154
BCCF8699

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Synthesis of 4-cyanoethylated benzoxazines by visible-light-promoted radical oxycyanomethylation of olefinic amides with bromoacetonitrile
Sun S, et al.
Tetrahedron Letters, 60(33), 150926-150926 (2019)
Carles Miró Sabaté et al.
Chemistry, an Asian journal, 7(5), 1085-1095 (2012-03-03)
1,1-Dimethylhydrazine can be readily alkylated with bromoacetonitrile to form 1-cyanomethyl-1,1-dimethylhydrazinium bromide ([(CH(3))(2)N(CH(2)CN)NH(2)]Br, 1). The metathesis reaction of compound 1 led to the formation of a new family of energetic salts based on the [(CH(3))(2)N(CH(2)CN)NH(2)](+) cation and nitrate (2), perchlorate (3)
The synthesis of three novel pendant armed macrocyclic ligands. The X-ray crystal structure of a cadmium complex derived from the first oxaazamacrocycle bearing two alkylated aromatic amine functions
Valencia L, et al.
Polyhedron, 20(26-27), 3091-3099 (2001)

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