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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:
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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

>149.0 °F - closed cup

Flash Point(C)

> 65 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Poisonous substance

PRTR

Class I Designated Chemical Substances

JAN Code

16772-VAR:
16772-BULK:
16772-1EA:
16772-1EA-BULK:
16772-200G:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
E. Gross
Methods in Enzymology, 11, 238-238 (1967)
Cyanogen bromide (CNBr).
Kumar V
Synlett, 2005(10), 1638-1639 (2005)
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