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

Name: Methyl 2-methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzoate
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CAS No. 525362-07-6
Cat. No. CS-0049158
Purity≥97%
MDL No.MFCD16996354

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Methyl 2-methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzoate|CS-0049158

Structure of 525362-07-6

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General Information

CAS No. 525362-07-6
Cat. No. CS-0049158
Purity ≥97%
MDL No. MFCD16996354
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₁BO₄
Molecular Weight None
Synonym(s) methyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate(WXC05916)
SMILES COC(=O)C1=C(C)C=C(C=C1)B1OC(C)(C)C(C)(C)O1

Description

Methyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate features a boronate ester group flanked by electron-rich tetramethylcyclopentadienone rings, enabling robust coupling in Suzuki-Miyaura reactions. This bench-stable reagent integrates seamlessly into C–C bond formation workflows, offering high functional group tolerance and predictable regiochemistry under standard conditions.

Application

Methyl 2-methyl-4-(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 sterically protected boronate ester exhibits excellent shelf stability and functional group tolerance, enabling reliable coupling with aryl halides and pseudohalides under mild conditions. Its methyl and ester groups provide orthogonal reactivity for downstream modifications, making it a practical scaffold in medicinal chemistry and materials synthesis workflows.

Synthesis

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  525362-07-6
References
- Imanishi, Masashi; Tomishima, Yasuyo; Itou, Shinji; Hamashima, Hitoshi; Nakajima, Yutaka; Washizuka, Kenichi; Sakurai, Minoru; 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, # 6 p. 1925 - 1944

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 : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-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-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzoate

CAS No. 525362-07-6

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