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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

Quality Level

100

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.)

functional group

bromo

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

494976-VAR:
494976-25ML:
494976-BULK:
494976-5ML:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCC9358
MKBR0869V
MKBH3290V
MKBG1053V
MKAA2224

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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)
Reactions of bromothianaphthenes with piperidine. Reinvestigation.
Reinecke MG, et al.
The Journal of Organic Chemistry, 38(7), 1365-1367 (1973)
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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