(5-Cyanothiophen-2-yl)boronic acid

Name: (5-Cyanothiophen-2-yl)boronic acid
Brand: ChemScene
Availability: InStock
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CAS No. 305832-67-1
Cat. No. CS-W007839
Purity≥98%
MDL No.MFCD02094029

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(5-Cyanothiophen-2-yl)boronic acid|CS-W007839

Structure of 305832-67-1

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General Information

CAS No. 305832-67-1
Cat. No. CS-W007839
Purity ≥98%
MDL No. MFCD02094029
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₄BNO₂S
Molecular Weight 152.97
Synonym(s) 5-Cyanothiophene-2-boronic acid
SMILES C1=C(SC(=C1)C#N)B(O)O

Description

This boronate moiety integrates a cyano-substituted thiophene scaffold, delivering enhanced stability and electron-withdrawing character. The para-cyano group modulates reactivity, enabling efficient cross-coupling under standard conditions. This bench-stable reagent facilitates direct access to functionalized heteroaryl architectures in synthetic workflows.

Application

(5-Cyanothiophen-2-yl)boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient access to functionalized thiophene derivatives. The cyano group enhances electronic modulation and provides a handle for further derivatization, while the boronic acid moiety offers excellent bench stability and compatibility with diverse reaction conditions. Its robustness and predictable reactivity make it ideal for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- 1003-31-2
- ~91%
- In-stock
  
  305832-67-1
References
- American Home Products Corporation; Ligand Pharmaceuticals, Inc. Patent: US6355648 B1, 2002 ; Location in patent: Page column 64 ; US 6355648 B1

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 64.25
LogP -0.70042
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

Key Words

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(5-Cyanothiophen-2-yl)boronic acid

CAS No. 305832-67-1

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