B57001
2-Bromobenzaldehyde
98%
Synonym(s):
2-Formylbromobenzene
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About This Item
Linear Formula:
BrC6H4CHO
CAS Number:
Molecular Weight:
185.02
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
229-622-2
Beilstein/REAXYS Number:
636132
MDL number:
Assay:
98%
Form:
liquid
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
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.
signalword
Warning
hcodes
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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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)
Enantioselective total synthesis of (?)-taxol.
Kusama H, et al.
Journal of the American Chemical Society, 122(16), 3811-3820 (2000)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| C0780-500G | 04061833452134 |
| C0780-100G | 04061833452103 |
| C0780-10MG | 04061833452127 |
| C0780-50G | 04061833452172 |
| B57001-10G | 04061833434079 |
| B57001-25G | 04061833434086 |