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B57001 Sigma-Aldrich

2-Bromobenzaldehyde

98%

Synonym: 2-Formylbromobenzene

  • CAS Number 6630-33-7

  • Linear Formula BrC6H4CHO

  • Molecular Weight 185.02

  •  Beilstein/REAXYS Number 636132

  •  EC Number 229-622-2

  •  MDL number MFCD00003300

  •  PubChem Substance ID 24891854

  •  NACRES NA.22

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Properties

Related Categories Aldehydes, Building Blocks, C7, Carbonyl Compounds, Chemical Synthesis,
Quality Level   100
assay   98%
refractive index   n20/D 1.595 (lit.)
bp   230 °C (lit.)
mp   16-19 °C (lit.)
density   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
InChI key   NDOPHXWIAZIXPR-UHFFFAOYSA-N

Description

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.

Packaging

10, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
203.0 °F - closed cup
Flash Point(C) 
95 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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