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B81255

Sigma-Aldrich

N-Bromosuccinimide

99%, for peptide synthesis, ReagentPlus®

Synonym(s):

NBS

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5 G
€37.60
100 G
€44.80
250 G
€53.40
500 G
€94.70
1 KG
€188.00
5 KG
€585.00

About This Item

Empirical Formula (Hill Notation):
C4H4BrNO2
CAS Number:
Molecular Weight:
177.98
Beilstein:
113916
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

€37.60


Please contact Customer Service for Availability

Request a Bulk Order

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

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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, 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
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
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

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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