2-(4-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-(4-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 73852-88-7
Cat. No. CS-0036744
Purity≥97%
MDL No.None

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2-(4-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0036744

Structure of 73852-88-7

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General Information

CAS No. 73852-88-7
Cat. No. CS-0036744
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₆BIO₂
Molecular Weight 329.97
Synonym(s) 4-Iodobenzeneboronic Acid Pinacol Ester
SMILES CC1(C)C(C)(C)OB(C2=CC=C(I)C=C2)O1

Description

This boronate ester features a 4-iodophenyl group conjugated to a tetramethyl-substituted dioxaborolane ring, enabling efficient Suzuki-Miyaura cross-coupling under standard conditions. The steric shielding provided by the four methyl groups enhances stability and reduces protodeboronation, while the iodide moiety ensures high reactivity in palladium-catalyzed transformations.

Application

2-(4-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent for Suzuki-Miyaura cross-coupling reactions. Its iodide functionality enables orthogonal activation in multi-step synthesis, while the sterically protected dioxaborolane ring ensures high thermal stability and resistance to protodeboronation. The compound facilitates efficient C–C bond formation with aryl halides under mild conditions, offering excellent functional group tolerance and reliable scalability in pharmaceutical and materials chemistry workflows.

Synthesis

Route1
- In-stock
  
  76-09-5
- 22092-92-8
- 1514-50-7
- ~79%
- In-stock
  
  73852-88-7
References
- UNIVERSITE DE BORDEAUX 1; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; PUCHEAULT, Mathieu Jonathan Damien; MARCIASINI, Ludovic Daniel Alain; VAULTIER, Michel Patent: WO2014/9169 A1, 2014 ; Location in patent: Page/Page column 53-54; 69 ;
Route2
- In-stock
  
  624-38-4
- In-stock
  
  1195-66-0
- ~91%
- In-stock
  
  73852-88-7
References
- Baron, Oliver; Knochel, Paul Angewandte Chemie - International Edition, 2005 , vol. 44, # 20 p. 3133 - 3135
Route3
- In-stock
  
  76-09-5
- In-stock
  
  5122-99-6
- ~92%
- In-stock
  
  73852-88-7
References
- Aquino, Maurizio; Guerrero, Maria D.; Bruno, Ines; Terencio, Maria C.; Paya, Miguel; Riccio, Raffaele Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 19 p. 9056 - 9064

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 18.46
LogP 2.5904
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

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2-(4-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 73852-88-7

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