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

Name: 2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
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CAS No. 627906-52-9
Cat. No. CS-0089467
Molecule weight234.10
Purity≥98%
MDL No.MFCD16994279

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2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol|CS-0089467

Structure of 627906-52-9

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General Information

CAS No. 627906-52-9
Cat. No. CS-0089467
Purity ≥98%
MDL No. MFCD16994279
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₉BO₃
Molecular Weight 234.10
Synonym(s) 4-Hydroxy-3-methylphenylboronic Acid Pinacol Ester
SMILES CC(O1)(C)C(C)(C)OB1C2=CC(C)=C(O)C=C2

Description

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol features a boronate ester group flanked by electron-rich and sterically shielded tetramethylcyclopentadienone moieties, enabling stable coupling in Suzuki-Miyaura reactions. This bench-stable reagent integrates readily into complex molecular architectures, delivering efficient access to functionalized biaryls under mild conditions.

Application

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol serves as a robust boronate building block in Suzuki-Miyaura cross-coupling reactions. Its stability under ambient conditions and tolerance to diverse functional groups enable reliable C–C bond formation with aryl and heteroaryl halides. The ortho-methyl group enhances regioselectivity in coupling processes, while the pinacol boronate moiety facilitates purification and minimizes protodeboronation. This compound functions effectively in the synthesis of biaryl scaffolds common in pharmaceutical and agrochemical development.

Synthesis

Route1
- In-stock
  
  2362-12-1
- In-stock
  
  73183-34-3
- ~67%
- In-stock
  
  627906-52-9
References
- Williams, Anna B.; Hanson, Robert N. Tetrahedron, 2012 , vol. 68, # 27-28 p. 5406 - 5414
Route2
- 95-48-7
- ~%
- In-stock
  
  627906-52-9
References
- Williams, Anna B.; Hanson, Robert N. Tetrahedron, 2012 , vol. 68, # 27-28 p. 5406 - 5414

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

Quality Control

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Computational Chemistry Data

TPSA 38.69
LogP 1.99982
H_Acceptors 3
H_Donors 1
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-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

CAS No. 627906-52-9

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