B81255

N-Bromosuccinimide

99%, for peptide synthesis, ReagentPlus^®

• Synonyme(s) : NBS
• Formule empirique (notation de Hill) : C₄H₄BrNO₂
• CAS Number: 128-08-5
• Poids moléculaire : 177.98
• Beilstein: 113916
• Numéro CE : 204-877-2
• Numéro MDL: MFCD00005510
• Code UNSPSC : 12352101
• ID de substance PubChem : 57653959
• Nomenclature NACRES : NA.22

Propriétés

• Product Name: N-Bromosuccinimide, ReagentPlus^®, 99%
• Niveau de qualité: 200
• Gamme de produits: ReagentPlus^®
• Essai: 99%
• Forme: powder
• Pf: 175-180 °C (dec.) (lit.)
• Application(s): peptide synthesis
• Température de stockage: 2-8°C
• Chaîne SMILES: BrN1C(=O)CCC1=O
• InChI: 1S/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
• Clé InChI: PCLIMKBDDGJMGD-UHFFFAOYSA-N

Description

Description générale

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.

Caractéristiques et avantages

NBS is an easier and safer brominating agent to handle than bromine.

Informations légales

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Informations sur la sécurité

• Pictogrammes: GHS03,GHS08,GHS05,GHS07,GHS09
• Mention d'avertissement: Warning
• Mentions de danger: H272,H290,H315,H317,H319,H341,H400
• Conseils de prudence: P210 - P273 - P280 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Classification des risques: Aquatic Acute 1 - Eye Irrit. 2 - Met. Corr. 1 - Muta. 2 - Ox. Sol. 3 - Skin Irrit. 2 - Skin Sens. 1B
• Code de la classe de stockage: 5.1B - Oxidizing hazardous materials
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges