B57001
2-Bromobenzaldehyde
98%
Synonym(s):
2-Formylbromobenzene
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About This Item
Linear Formula:
BrC6H4CHO
CAS Number:
Molecular Weight:
185.02
Beilstein:
636132
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
203.0 °F - closed cup
Flash Point(C)
95 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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A gold-catalyzed domino process to the steroid framework.
Hildebrandt D and Dyker G
The Journal of Organic Chemistry, 71(18), 6728-6733 (2006)
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)
Enantioselective total synthesis of (?)-taxol.
Kusama H, et al.
Journal of the American Chemical Society, 122(16), 3811-3820 (2000)
Palladium-catalyzed one-pot Suzuki-Miyaura cross coupling followed by oxidative lactonization: a novel and efficient route for the one-pot synthesis of benzo [c] chromene-6-ones
R Singha, et al.
Tetrahedron Letters, 54, 657-660 (2013)
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