5-Bromobenzo[b]thiophene-3-carbaldehyde

CAS No. 16296-72-3
Cat. No. CS-0114084
Purity≥97%
MDL No.MFCD00858578

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5-Bromobenzo[b]thiophene-3-carbaldehyde|CS-0114084

Structure of 16296-72-3

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Description

5-Bromobenzo[b]thiophene-3-carbaldehyde features a brominated benzo[b]thiophene core paired with a reactive aldehyde group, enabling direct incorporation into Suzuki-Miyaura couplings and other cross-coupling transformations. The electron-deficient thiophene ring enhances reactivity in transition metal catalysis, while the aldehyde functionality provides a handle for further derivatization via imine formation or reductive amination. This scaffold is well-suited for synthesizing advanced heterocyclic architectures in medicinal chemistry and materials science.

Application

5-Bromobenzo[b]thiophene-3-carbaldehyde serves as a versatile building block for the synthesis of bioactive heterocycles and functionalized pharmaceutical intermediates. The aldehyde group enables direct coupling reactions, including Wittig, Grignard, and reductive amination, while the bromine substituent facilitates palladium-catalyzed cross-coupling transformations. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for iterative synthetic strategies in medicinal chemistry and materials science.

General Information

CAS No. 16296-72-3
Cat. No. CS-0114084
Purity ≥97%
MDL No. MFCD00858578
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₅BrOS
Molecular Weight 241.10
Synonym(s) 5-BROMOBENZO[B]THIOPHENE-3-CARBOXALDEHYDE
SMILES O=CC1=CSC2=CC=C(Br)C=C21

Computational Chemistry Data

TPSA 17.07
LogP 3.4763
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501

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Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Benzothiophene compounds

Key Words

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5-Bromobenzo[b]thiophene-3-carbaldehyde

CAS No. 16296-72-3

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