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3-Bromo-1-benzothiophene

Product Name3-Bromo-1-benzothiophene
CAS7342-82-7
MFC8H5BrS
MW213.1
EINECS
MOL File7342-82-7.mol

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
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Colorless to yellow to red liquid

Uses

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

Uses

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

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

6287-82-7

7342-82-7

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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