N-BROMOSUCCINIMIDE REAGENTPLUS 99% (C005B-013499)

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 Sigma-Aldrich Co. LLC

Molecular Weight: 177.98. Empirical Formula: C₄H₄BrNO₂. 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. Pictograms: GHS03,GHS05,GHS07,GHS08,GHS09. Signal Word: Warning. Hazard Statements: H272 - H290 - H315 - H317 - H319 - H341 - H400. Precautionary Statements: 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 Code: 5.1B - Oxidizing hazardous materials. WGK: WGK 3. Flash Point(F): Not applicable. Flash Point(C): Not applicable. Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges.