3-Bromo-1-benzothiophene Chemical Properties

Melting point:

146-156 °C

Boiling point:

269 °C/752.5 mmHg (lit.)

Density 

1.629 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.668(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Sparingly Soluble (0.14 g/L) (25°C).

form 

clear liquid

color 

Light yellow to Brown

InChI

InChI=1S/C8H5BrS/c9-7-5-10-8-4-2-1-3-6(7)8/h1-5H

InChIKey

SRWDQSRTOOMPMO-UHFFFAOYSA-N

SMILES

C12=CC=CC=C1C(Br)=CS2

CAS DataBase Reference

7342-82-7(CAS DataBase Reference)

NIST Chemistry Reference

Benzo[b]thiophene, 3-bromo-,(7342-82-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

3-Bromo-1-benzothiophene Usage And Synthesis

Chemical Properties

Colorless to yellow to red liquid

Uses

Antifungal activity of synthetic di (hetero) arylamines based on the benzo [b] thiophene moiety.

Uses

3-Bromothianaphthene may be used in the synthesis of (benzo[b]thiophen-3-yl)trimethylstannane.

General Description

3-Bromothianaphthene is a heteroaryl halide. It undergoes Suzuki-Miyaura reaction with phenylboronic acid (PBA) or 3-thienylboronic acid in the presence of a novel heterogeneous Pd catalyst [Pd@PDEB, PDEB=poly(1,3-diethynylbenzene)]. The substitution reaction of 3-bromothianaphthene with piperidine to form 3-piperidinothianaphthene as the major product has been reported.

Synthesis

The general procedure for the synthesis of 3-bromobenzothiophene from 2,3-dibromothiophene was as follows: first, the halogenated heterocycle (0.66 mmol) was dissolved in anhydrous THF (13.2 mL) and degassed by drumming in argon for a few minutes. Subsequently, PdCl2 (dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were added sequentially. The reaction mixture was stirred at room temperature for appropriate time under argon protection and finally post-treated according to standard methods.

References

[1] Journal of Organic Chemistry, 2012, vol. 77, # 21, p. 9921 - 9925,5
[2] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209
[3] Patent: WO2015/188790, 2015, A1. Location in patent: Page/Page column 22

3-Bromo-1-benzothiophene(7342-82-7)Related Product Information

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