2-Bromo-3-nitrothiophene

Name: 2-Bromo-3-nitrothiophene
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CAS No. 2161-96-8
Cat. No. CS-W003136
Purity≥95%
MDL No.MFCD04037319

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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+
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General Information

CAS No. 2161-96-8
Cat. No. CS-W003136
Purity ≥95%
MDL No. MFCD04037319
Storage -20°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄H₂BrNO₂S
Molecular Weight 208.03
Synonym(s) 2-Bromo-3-nitrothiphene
SMILES O=[N+](C1=C(Br)SC=C1)[O-]

Description

2-Bromo-3-nitrothiophene features a thiophene core bearing bromine at the 2-position and a nitro group at the 3-position, creating a highly functionalized heterocycle. This combination enables direct coupling in cross-coupling reactions and facilitates further derivatization through nucleophilic substitution or metal-catalyzed transformations. The electron-deficient nature of the ring enhances reactivity in transition metal-mediated processes.

Application

2-Bromo-3-nitrothiophene serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its bromine substituent. The nitro group enhances electrophilicity at the adjacent carbon, facilitating sequential functionalization. Its bench-stable crystalline form and compatibility with standard reaction conditions make it well-suited for iterative synthesis of complex thiophene-based scaffolds in medicinal chemistry and materials science.

Synthesis

Route1
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  89283-24-9
- ~%
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  2161-96-8
References
- Bl. Univ. Osaka Prefect, , vol. <A> 6, p. 127,130 Nippon Kagaku Zasshi, , vol. 78, p. 779,783 Chem.Abstr., , p. 22559

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-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 43.14
LogP 2.4188
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

Key Words

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2-Bromo-3-nitrothiophene

CAS No. 2161-96-8

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