B57001

2-Bromobenzaldehyde

98%

• Synonyme(s) : 2-Formylbromobenzene
• Formule linéaire : BrC₆H₄CHO
• Numéro CAS: 6630-33-7
• Poids moléculaire : 185.02
• Numéro Beilstein : 636132
• Numéro CE : 229-622-2
• Numéro MDL: MFCD00003300
• Code UNSPSC : 12352100
• ID de substance PubChem : 24891854
• Nomenclature NACRES : NA.22

Propriétés

• Niveau de qualité: 100
• Pureté: 98%
• Forme: liquid
• Indice de réfraction: n20/D 1.595 (lit.)
• Point d'ébullition: 230 °C (lit.)
• Pf: 16-19 °C (lit.)
• Densité: 1.585 g/mL at 25 °C (lit.)
• Chaîne SMILES: Brc1ccccc1C=O
• InChI: 1S/C7H5BrO/c8-7-4-2-1-3-6(7)5-9/h1-5H
• Clé InChI: NDOPHXWIAZIXPR-UHFFFAOYSA-N

Description

Description générale

2-Bromobenzaldehyde is a versatile building block used in Suzuki-Miyaura and Buchwald-Hartwig reactions, cross-coupling reactions to form carbon-carbon or carbon-heteroatom bonds

Application

Synthetic applications of 2-bromobenzaldehyde include:

• Synthesis of aza-fused polycyclic quinolines through copper-catalyzed cascade reaction.
• Preparation of 1-substituted indazoles by CuI-catalyzed coupling with N-aryl hydrazides.
• It is a key starting material in the total synthesis of an anticancer agent, (-)-taxol.
• Palladium/copper-catalyzed coupling and cyclization of terminal acetylenes derived from 2-bromobenzaldehyde and unsaturated imines can be used in the synthesis of wide range of isoquinolines, including decumbenine B.
• Fluoren-9-ones can be synthesized by annulation of arynes, generated in situ from 2-(trimethylsilyl)aryl triflates, with 2-bromobenzaldehyde in the presence of palladium(0) catalyst.
• It can also be used to build a variety of steroid frameworks, in which ring A is derived from 2-bromobenzaldehyde.

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H315,H319,H335
• Conseils de prudence: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Organes cibles: Respiratory system
• Code de la classe de stockage: 10 - Combustible liquids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): 203.0 °F - closed cup
• Point d'éclair (°C): 95 °C - closed cup
• Équipement de protection individuelle: Eyeshields, Gloves, type ABEK (EN14387) respirator filter