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B81255

Sigma-Aldrich

N-Bromosuccinimide

99%, for peptide synthesis, ReagentPlus®

Synonym(s):

NBS

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About This Item

Empirical Formula (Hill Notation):
C4H4BrNO2
CAS Number:
128-08-5
Molecular Weight:
177.98
Beilstein:
113916
EC Number:
204-877-2
MDL number:
MFCD00005510
UNSPSC Code:
12352101
PubChem Substance ID:
57653959
NACRES:
NA.22

product name

N-Bromosuccinimide, ReagentPlus®, 99%

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Synlett, 347-347 (1990)
Laura Vallejo-Torres et al.
Pediatrics, 136(2), e424-e432 (2015-07-15)
There are conflicting views as to whether testing for biotinidase deficiency (BD) ought to be incorporated into universal newborn screening (NBS) programs. The aim of this study was to evaluate the cost-effectiveness of adding BD to the panel of conditions
Rune Dietz et al.
Environmental research, 140, 45-55 (2015-04-01)
Polar bears (Ursus maritimus) consume large quantities of seal blubber and other high trophic marine mammals and consequently have some of the highest tissue concentrations of organohalogen contaminants (OHCs) among Arctic biota. In the present paper we carried out a
Laurence S Freedman et al.
American journal of epidemiology, 181(7), 473-487 (2015-03-20)
We pooled data from 5 large validation studies (1999-2009) of dietary self-report instruments that used recovery biomarkers as referents, to assess food frequency questionnaires (FFQs) and 24-hour recalls (24HRs). Here we report on total potassium and sodium intakes, their densities
Synlett, 345-345 (1990)
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