B81255

N-Bromosuccinimide

99%, for peptide synthesis, ReagentPlus^®

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

Properties

• 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

Description

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

Safety Information

• pictograms: GHS03,GHS08,GHS05,GHS07,GHS09
• signalword: Warning
• hcodes: H272,H290,H315,H317,H319,H341,H400
• pcodes: P210 - P273 - P280 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• 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_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges