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B57001

Sigma-Aldrich

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
Beilstein:
636132
EC Number:
229-622-2
MDL number:
MFCD00003300
UNSPSC Code:
12352100
PubChem Substance ID:
24891854
NACRES:
NA.22

Quality Level

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.)

SMILES string

Brc1ccccc1C=O

InChI

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

InChI key

NDOPHXWIAZIXPR-UHFFFAOYSA-N

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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

203.0 °F

Flash Point(C)

95 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Assembly of N, N-Disubstituted Hydrazines and 1-Aryl-1 H-indazoles via Copper-Catalyzed Coupling Reactions.
Xiong X, et al.
Organic Letters, 14(10), 2552-2555 (2012)
Synthesis of isoquinolines and pyridines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes and unsaturated imines: the total synthesis of decumbenine B.
Roesch K R and Larock R C
The Journal of Organic Chemistry, 67(1), 86-94 (2002)
A gold-catalyzed domino process to the steroid framework.
Hildebrandt D and Dyker G
The Journal of Organic Chemistry, 71(18), 6728-6733 (2006)
Xiaoxia Zhang et al.
Organic letters, 7(18), 3973-3976 (2005-08-27)
Arynes, generated in situ from 2-(trimethylsilyl)aryl triflates and CsF, undergo annulation by o-haloarenecarboxaldehydes in the presence of a Pd catalyst, providing a useful new method for the synthesis of fluoren-9-ones in good yields. [reaction: see text]
Enantioselective total synthesis of (?)-taxol.
Kusama H, et al.
Journal of the American Chemical Society, 122(16), 3811-3820 (2000)
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