Methyl 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Name: Methyl 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
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CAS No. 478375-39-2
Cat. No. CS-0041216
Purity≥97%
MDL No.MFCD16996355

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Methyl 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate|CS-0041216

Structure of 478375-39-2

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General Information

CAS No. 478375-39-2
Cat. No. CS-0041216
Purity ≥97%
MDL No. MFCD16996355
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₁BO₄
Molecular Weight 276.14
Synonym(s) 3-(methoxycarbonyl)-4-methylphenylboronic acid,pinacol ester
SMILES O=C(OC)C1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1C

Description

Methyl 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate delivers a sterically protected boronate ester that integrates readily into Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane moiety enhances stability and solubility under standard conditions, while the methyl and ester groups provide orthogonal functionality for further derivatization.

Application

Methyl 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The pinacol boronate group enables stable, bench-ready handling and high functional group tolerance. It facilitates efficient C–C bond formation with aryl and heteroaryl halides under mild conditions, making it ideal for constructing complex biaryls and functionalized aromatic scaffolds in medicinal chemistry and materials science applications.

Synthesis

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  478375-39-2
References
- Imanishi, Masashi; Nakajima, Yutaka; Tomishima, Yasuyo; Hamashima, Hitoshi; Washizuka, Kenichi; Sakurai, Minora; Matsui, Shigeo; Imamura, Emiko; Ueshima, Koji; Yamamoto, Takao; Yamamoto, Nobuhiro; Ishikawa, Hirofumi; Nakano, Keiko; Unami, Naoko; Hamada, Kaori; Matsumura, Yasuhiro; Takamura, Fujiko; Hattori, Kouji Journal of Medicinal Chemistry, 2008 , vol. 51, # 15 p. 4804 - 4822

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-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 44.76
LogP 2.08082
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Methyl 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

CAS No. 478375-39-2

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