4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile

Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile
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CAS No. 1642844-61-8
Cat. No. CS-0369162
Purity≥97%
MDL No.None

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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile|CS-0369162

Structure of 1642844-61-8

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General Information

CAS No. 1642844-61-8
Cat. No. CS-0369162
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₄BNO₂S
Molecular Weight 235.11
Synonym(s) 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbonitrile
SMILES N#CC1=CC(B2OC(C)(C)C(C)(C)O2)=CS1

Description

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile features a boronate ester group coupled to a thiophene scaffold bearing a nitrile at the 2-position. This combination enables efficient Suzuki-Miyaura coupling under mild conditions while maintaining stability during storage and handling. The electron-withdrawing nitrile enhances reactivity in cross-coupling processes.

Application

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylborolane moiety enables stable, air-tolerant handling and efficient coupling with aryl, heteroaryl, and vinyl halides. The thiophene core with nitrile functionality provides a rigid, electron-deficient scaffold useful in constructing conjugated systems for materials science and medicinal chemistry applications.

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-P362+P364-P501

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Computational Chemistry Data

TPSA 42.25
LogP 1.91898
H_Acceptors 4
H_Donors 0
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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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile

CAS No. 1642844-61-8

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