3-Bromo-5-nitrobenzo[b]thiophene

Name: 3-Bromo-5-nitrobenzo[b]thiophene
Brand: ChemScene
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CAS No. 19492-95-6
Cat. No. CS-0188214
Purity≥96%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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3-Bromo-5-nitrobenzo[b]thiophene|CS-0188214

Structure of 19492-95-6

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General Information

CAS No. 19492-95-6
Cat. No. CS-0188214
Purity ≥96%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₄BrNO₂S
Molecular Weight 258.09
Synonym(s) 3-Bromo-5-nitrothionaphthene
SMILES O=[N+](C1=CC2=C(SC=C2Br)C=C1)[O-]

Description

3-Bromo-5-nitrobenzo[b]thiophene features a fused thiophene core with complementary electron-withdrawing nitro and bromo substituents at meta positions, enabling direct functionalization in cross-coupling reactions. This configuration enhances reactivity while maintaining stability under standard conditions.

Application

3-Bromo-5-nitrobenzo[b]thiophene serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its bromo substituent. The nitro group provides a strong electron-withdrawing effect, enhancing electrophilicity and facilitating subsequent transformations such as reduction to an amine or participation in nucleophilic aromatic substitution. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  4965-26-8
- ~%
- In-stock
  
  19492-95-6
References
- Bordwell; Albisetti Journal of the American Chemical Society, 1948 , vol. 70, p. 1955,1957
Route2
- In-stock
  
  6345-55-7
- ~%
- In-stock
  
  19492-95-6
References
- Bordwell; Albisetti Journal of the American Chemical Society, 1948 , vol. 70, p. 1955,1957

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H312-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 43.14
LogP 3.572
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Benzothiophene compounds

Key Words

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3-Bromo-5-nitrobenzo[b]thiophene

CAS No. 19492-95-6

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