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16772

Sigma-Aldrich

Cyanogen bromide

≥98.5% (RT)

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Synonym(s):
Bromine cyanide
Linear Formula:
BrCN
CAS Number:
506-68-3
Molecular Weight:
105.92
Beilstein:
1697296
EC Number:
208-051-2
MDL number:
MFCD00011597
UNSPSC Code:
12352100
PubChem Substance ID:
57647589
NACRES:
NA.22

vapor density

3.65 (vs air)

Quality Level

200

vapor pressure

100 mmHg ( 22.6 °C)

Assay

≥98.5% (RT)

form

crystals

bp

61-62 °C (lit.)

mp

50-53 °C (lit.)

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 and cleavage.
  • Under von Braun reaction conditions, CNBr reacts with tertiary amines to yield respective organocyanamides.
  • 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.

Other Notes

Reagent for the selective cleavage of peptide bonds (e.g. methionine)

Signal Word

Danger

Hazard Classifications

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

Supplementary Hazards

EUH032

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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)
The von Braun Reaction Applied to Azetidines.
Wright K, et al.
European Journal of Organic Chemistry, 2017(47), 195-7201 (2017)
von Braun reaction.
Name Reactions, 562-563 (2009)
New Protocol for the Synthesis of 2-Alkanoyl-and 2-Aryloyl-5, 5-dimethylcyclohexane-1, 3-diones by the Reaction of Dimedone with Various Aldehydes and Cyanogen Bromide in the Presence of Triethylamine.
Kashani E, et al.
Synthesis, 48(13), 2079-2084 (2016)
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