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494976

Sigma-Aldrich

3-Bromothianaphthene

95%

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Synonym(s):
3-Bromobenzo[b]thiophene
Empirical Formula (Hill Notation):
C8H5BrS
CAS Number:
Molecular Weight:
213.09
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

refractive index

n20/D 1.668 (lit.)

bp

269 °C/752.5 mmHg (lit.)

density

1.629 g/mL at 25 °C (lit.)

SMILES string

Brc1csc2ccccc12

InChI

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

InChI key

SRWDQSRTOOMPMO-UHFFFAOYSA-N

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This Item
145610136727218006
3-Bromothianaphthene 95%

494976

3-Bromothianaphthene

3-(Bromomethyl)benzonitrile 95%

145610

3-(Bromomethyl)benzonitrile

3-Chlorobenzyl bromide 97%

136727

3-Chlorobenzyl bromide

5-Chloro-3-hydroxypyridine 99%

218006

5-Chloro-3-hydroxypyridine

bp

269 °C/752.5 mmHg (lit.)

bp

-

bp

109-110 °C/12 mmHg (lit.)

bp

-

refractive index

n20/D 1.668 (lit.)

refractive index

-

refractive index

n20/D 1.588 (lit.)

refractive index

-

density

1.629 g/mL at 25 °C (lit.)

density

-

density

1.565 g/mL at 25 °C (lit.)

density

-

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.

Application

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Reactions of bromothianaphthenes with piperidine. Reinvestigation.
Reinecke MG, et al.
The Journal of Organic Chemistry, 38(7), 1365-1367 (1973)
Reusable, Highly Active Heterogeneous Palladium Catalyst by Convenient Self-Encapsulation Cross-Linking Polymerization for Multiple Carbon-Carbon Cross-Coupling Reactions at ppm to ppb Palladium Loadings.
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