B81255
N-Bromosuccinimide
99%, for peptide synthesis, ReagentPlus®
Synonym(s):
NBS
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About This Item
Empirical Formula (Hill Notation):
C4H4BrNO2
CAS Number:
Molecular Weight:
177.98
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352101
EC Number:
204-877-2
MDL number:
Beilstein/REAXYS Number:
113916
Product Name
N-Bromosuccinimide, ReagentPlus®, 99%
Quality Segment
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
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
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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
5.1B - Oxidizing hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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