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Sigma-Aldrich

N-Bromosuccinimide

ReagentPlus®, 99%

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Synonym(s):
NBS
Empirical Formula (Hill Notation):
C4H4BrNO2
CAS Number:
128-08-5
Molecular Weight:
177.98
Beilstein:
113916
EC Number:
204-877-2
MDL number:
MFCD00005510
PubChem Substance ID:
57653959
NACRES:
NA.22

Quality Level

200

product line

ReagentPlus®

Assay

99%

form

powder

mp

175-180 °C (dec.) (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

BrN1C(=O)CCC1=O

InChI

1S/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2

InChI key

PCLIMKBDDGJMGD-UHFFFAOYSA-N

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General description

N-Bromosuccinimide (NBS) is an organic compound commonly used as a brominating agent in organic synthesis. It is a convenient source of bromine radicals. It is used in radical bromination of allylic and benzylic positions. Additionally, NBS is also used as a reagent in electrophilic addition and electrophilic substitution reactions in organic chemistry.

Application

N-Bromosuccinimide can be used as a reagent:      
  • In the Wohl-Ziegler reaction (bromination at allylic positions via a radical pathway).      
  • To synthesize benzils and aliphatic 1,2-diketones from hydrobenzoins and 1,2-diols in the presence of CCl4 as a solvent.      
  • To prepare tricyclic azepino[4,5-b]indoles from indole-β-enaminoesters or β-enaminones via Pictet–Spengler cyclization.
  • To synthesize acylsilanes via oxidative hydrolysis of 2-silyl-1,3-dithianes.

Versatile brominating agent. For the oxidation of tryptophan though tyrosine, histidine and methionine residues may be oxidized to a lesser extent. Also used for the modification of ribosomal sulfhydryl groups.

Features and Benefits

NBS is an easier and safer brominating agent to handle than bromine.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Warning

Hazard Classifications

Aquatic Acute 1 - Eye Irrit. 2 - Met. Corr. 1 - Muta. 2 - Ox. Sol. 3 - Skin Irrit. 2 - Skin Sens. 1B

Storage Class Code

5.1B - Oxidizing hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synlett, 347-347 (1990)
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