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B57001

2-Bromobenzaldehyde

98%

Synonym(s):

2-Formylbromobenzene

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About This Item

Linear Formula:
BrC6H4CHO
CAS Number:
6630-33-7
Molecular Weight:
185.02
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24891854
EC Number:
229-622-2
Beilstein/REAXYS Number:
636132
MDL number:
MFCD00003300
Assay:
98%
Form:
liquid
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Quality Segment

100

assay

98%

form

liquid

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.)

functional group

aldehyde, bromo

SMILES string

Brc1ccccc1C=O

InChI

1S/C7H5BrO/c8-7-4-2-1-3-6(7)5-9/h1-5H

InChI key

NDOPHXWIAZIXPR-UHFFFAOYSA-N

General description

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

203.0 °F - closed cup

flash_point_c

95 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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