5-Bromo-1-benzofuran Chemical Properties

Melting point:

8°C(lit.)

Boiling point:

226°C(lit.)

Density 

1.573 g/mL at 25 °C

refractive index 

n20/D1.605

storage temp. 

Sealed in dry,Room Temperature

form 

liquid

color 

Colourless to light yellow

InChI

InChI=1S/C8H5BrO/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5H

InChIKey

AYOVPQORFBWFNO-UHFFFAOYSA-N

SMILES

O1C2=CC=C(Br)C=C2C=C1

CAS DataBase Reference

23145-07-5(CAS DataBase Reference)

EPA Substance Registry System

Benzofuran, 5-bromo- (23145-07-5)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29329990

5-Bromo-1-benzofuran Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

5-Bromobenzofuran is used in the synthesis of 1-(7-benzofuranyl)-4-methylpiperazine; a compound shown to bind strongly and with high selectivity to the serotonin receptor 5-HT2A in the presence of the receptor 5-HT7 in vitro.

Synthesis

The general procedure for the synthesis of 5-bromobenzofuran from 4-bromophenoxyacetaldehyde diethyl acetal was as follows: polyphosphoric acid (10 g) was added to a solution of benzene (50 mL), the product of step A (8.4 g). The reaction mixture was heated to reflux for 4 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and slowly poured into ice water (80 mL). The aqueous phase was extracted with ether and the organic phases were combined. The ether layer was washed sequentially with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 4.9 g of crude product in 85% yield.

References

[1] Patent: WO2004/33440, 2004, A1. Location in patent: Page 239-240
[2] Patent: US2004/147559, 2004, A1. Location in patent: Page 122
[3] Patent: US2004/106794, 2004, A1. Location in patent: Page 123
[4] Patent: WO2005/66147, 2005, A1. Location in patent: Page/Page column 209
[5] Patent: WO2005/68460, 2005, A1. Location in patent: Page/Page column 203

5-Bromo-1-benzofuran(23145-07-5)Related Product Information

• Benzofuran
• Furan
• 1,2-Dibromobenzene
• 4'-Bromopropiophenone
• 3-Bromoanisole
• 4-Bromofluorobenzene
• 2-Bromobenzonitrile
• 1,3-Dibromobenzene
• 5-BROMO-1-BENZOFURAN-2-CARBOXYLIC ACID
• Bromine
• 1-(5-BROMO-1-BENZOFURAN-2-YL)ETHANONE
• 3,5-DIBROMOBENZO[B]FURAN
• 6-CHLORO-BENZOFURAN-3-ONE
• 7-BROMO-1-BENZOFURAN-2-CARBOXYLICACID
• METHYL-7-BROMO-1-BENZOFURAN-2-CARBOXYLATE
• ethyl 2-(5-bromobenzofuran-3-yl)acetate
• 4-Fluoro-7-bromobenzofuran
• 5-BROMOBENZO[B]FURAN-2-CARBONYL CHLORIDE