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

Name: 2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
Brand: ChemScene
Availability: InStock
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CAS No. 629658-06-6
Cat. No. CS-0011731
Purity≥95%
MDL No.MFCD09260490

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FedEx Limited Quantities Ground	$0.00
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2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol|CS-0011731

Structure of 629658-06-6

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General Information

CAS No. 629658-06-6
Cat. No. CS-0011731
Purity ≥95%
MDL No. MFCD09260490
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₆BClO₃
Molecular Weight 254.52
Synonym(s) 2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol; 3-Chloro-4-hydroxyphenylboronic acid, pinacol ester
SMILES OC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1Cl

Description

2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol features a boronate ester group enabling efficient Suzuki-Miyaura coupling, paired with a chlorinated aromatic ring for orthogonal reactivity. This bench-stable reagent integrates seamlessly into complex molecule synthesis under standard conditions.

Application

2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The pinacol boronate group enables stable, air-tolerant handling and facilitates efficient coupling with aryl halides under mild conditions. Its ortho-chloro substituent provides complementary reactivity for sequential functionalization or cyclization processes. This compound functions as a key intermediate in the synthesis of biaryl scaffolds, particularly relevant to pharmaceutical and agrochemical research.

Synthesis

Route1
- In-stock
  
  3964-56-5
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  629658-06-6
References
- WO2003/99796 A1, ; Page 52-53 ; WO 03/099796 A1

Safety Information

Download SDS

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 : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 38.69
LogP 2.3448
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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

CAS No. 629658-06-6

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