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494976

Sigma-Aldrich

3-Bromothianaphthene

95%

Synonym(s):

3-Bromobenzo[b]thiophene

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About This Item

Empirical Formula (Hill Notation):
C8H5BrS
CAS Number:
7342-82-7
Molecular Weight:
213.09
MDL number:
MFCD00023009
UNSPSC Code:
12352100
PubChem Substance ID:
24872939
NACRES:
NA.22

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
Dong Z and Ye Z.
Advanced Synthesis & Catalysis, 356(16), 3401-3414 (2014)
Electronic influence of the thienyl sulfur atom on the oligomerization of ethylene by cobalt (II) 6-(thienyl)-2-(imino) pyridine catalysis.
Bianchini C, et al.
Organometallics, 26(3), 726-739 (2007)

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