2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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CAS No. 445303-10-6
Cat. No. CS-0174412
Purity≥98%
MDL No.None

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2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0174412

Structure of 445303-10-6

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General Information

CAS No. 445303-10-6
Cat. No. CS-0174412
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₈BClO₂
Molecular Weight 252.54
Synonym(s) 3-Chloro-4-methylphenylboronic acid pinacol ester
SMILES CC1=C(Cl)C=C(B2OC(C)(C(C)(O2)C)C)C=C1

Description

This boronate ester features a 3-chloro-4-methylphenyl group attached to a tetramethyl-substituted dioxaborolane ring, offering enhanced stability and moisture tolerance. It integrates readily into Suzuki-Miyaura cross-coupling reactions under standard conditions, enabling efficient C–C bond formation with aryl halides and triflates. The sterically protected boron center resists protodeboronation, ensuring high functional group compatibility in complex molecule synthesis.

Application

2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a robust boron building block for Suzuki-Miyaura cross-coupling reactions. Its stability under ambient conditions and tolerance to diverse functional groups enable reliable C–C bond formation in medicinal chemistry and materials synthesis. The tetramethyl substitution enhances shelf life and simplifies purification, making it ideal for high-throughput applications.

Synthesis

Route1
- 95-49-8
- 25015-63-8
- ~93%
- In-stock
  
  445303-10-6
References
- Frey, Guido D.; Rentzsch, Christoph F.; von Preysing, Denise; Scherg, Tobias; Muehlhofer, Michael; Herdtweck, Eberhardt; Herrmann, Wolfgang A. Journal of Organometallic Chemistry, 2006 , vol. 691, # 26 p. 5725 - 5738

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 18.46
LogP 2.94762
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 445303-10-6

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