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 Level
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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Synlett, 345-345 (1990)
Synlett, 347-347 (1990)
Silvio Neumann et al.
Polymers, 11(8) (2019-07-31)
The synthesis of polymers of intrinsic microporosity (PIM) modified with azide groups, the cross linkage by nitrene reaction and their performance as gas separation membranes are reported. The azide modification of the spirobisindane units in the polymer backbone was done
Global Trade Item Number
| SKU | GTIN |
|---|---|
| B81255-5G | 04061833442500 |
| B81255-5KG | 04061833556061 |
| B81255-100G | 04061833442470 |
| B81255-1KG | 04061833442487 |
| B81255-500G | 04061833442494 |