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16772

Sigma-Aldrich

Cyanogen bromide

≥98.5% (RT)

Synonym(s):

Bromine cyanide

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About This Item

Linear Formula:
BrCN
CAS Number:
Molecular Weight:
105.92
Beilstein/REAXYS Number:
1697296
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

3.65 (vs air)

Quality Level

vapor pressure

100 mmHg ( 22.6 °C)

assay

≥98.5% (RT)

form

crystals

bp

61-62 °C (lit.)

mp

50-53 °C (lit.)

functional group

bromo

storage temp.

2-8°C

SMILES string

BrC#N

InChI

1S/CBrN/c2-1-3

InChI key

ATDGTVJJHBUTRL-UHFFFAOYSA-N

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Application

  • Cyanogen bromide is widely used in protein immobilization[1][2] and cleavage.[3]
  • Under von Braun reaction conditions, CNBr reacts with tertiary amines to yield respective organocyanamides.[4][5]
  • It can also be used to synthesize organic intermediates like cyanuric bromide, derivatives of urea, guanidine, creatine, aryl nitriles, and a variety of heterocyclic compounds.[6][7][8][9]

Other Notes

Reagent for the selective cleavage of peptide bonds (e.g. methionine)[10][11]

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Eye Dam. 1 - Skin Corr. 1B

supp_hazards

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

>149.0 °F - closed cup

flash_point_c

> 65 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Straightforward Conversion of Alcohols into Nitriles.
Tarrade-Matha A, et al.
Synthetic Communications, 40(11), 1646-1649 (2010)
Synthesis of hindered chiral guanidine bases starting from (S)-(N, N-dialkyl-aminomethyl) pyrrolidines and BrCN.
Kohn U, et al.
Tetrahedron Asymmetry, 17(5), 811-818 (2006)
E. Gross
Methods in Enzymology, 11, 238-238 (1967)
R J Simpson et al.
Biochemistry international, 8(6), 787-791 (1984-06-01)
Herein we describe a procedure for the in situ cyanogen bromide cleavage of N-terminally blocked proteins which have been immobilised onto the glass fiber sample disk of the gas-phase sequencer. In this manner, new amino terminii suitable for automated Edman
Immobilization of lipases on hydrophobic supports involves the open form of the enzyme.
Manoel EA, et al.
Enz. Microbiol. Technol., 71, 53-57 (2015)

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