B57001

2-Brombenzaldehyd

98%

• Synonym(e): 2-Formylbromobenzene
• Lineare Formel: BrC₆H₄CHO
• CAS-Nummer: 6630-33-7
• Molekulargewicht: 185.02
• Beilstein: 636132
• EG-Nummer: 229-622-2
• MDL-Nummer: MFCD00003300
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24891854
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 100
• Assay: 98%
• Form: liquid
• Brechungsindex: n20/D 1.595 (lit.)
• bp: 230 °C (lit.)
• mp (Schmelzpunkt): 16-19 °C (lit.)
• Dichte: 1.585 g/mL at 25 °C (lit.)
• SMILES String: Brc1ccccc1C=O
• InChI: 1S/C7H5BrO/c8-7-4-2-1-3-6(7)5-9/h1-5H
• InChIKey: NDOPHXWIAZIXPR-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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

Anwendung

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.

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315,H319,H335
• P-Sätze: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 10 - Combustible liquids
• WGK: WGK 3
• Flammpunkt (°F): 203.0 °F - closed cup
• Flammpunkt (°C): 95 °C - closed cup
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type ABEK (EN14387) respirator filter