(2-Iodo-5-methoxyphenyl)boronic acid

Base Information

• Chemical Name: (2-Iodo-5-methoxyphenyl)boronic acid
• CAS No.: 89694-50-8
• Molecular Formula: C7H8BIO3
• Molecular Weight: 277.854
• Hs Code.: 2931900090
• Mol file: 89694-50-8.mol

Synonyms:(2-Iodo-5-methoxyphenyl)boronic acid;5-Methoxy-2-iodophenylboronic acid

Chemical Property of (2-Iodo-5-methoxyphenyl)boronic acid

Chemical Property:

• Melting Point: 202-207°C
• PSA: 49.69000
• LogP: -0.02040
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

(2-Iodo-5-methoxyphenyl)boronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: (2-Iodo-5-methoxyphenyl)boronic acid (5-methoxy-2-iodophenylboronic acid, MIBA) is an efficient catalyst for direct amidation reactions between carboxylic acids and amines. Its optimized structure, featuring a methoxy group para to the iodine, enhances electron density on the iodine, improving catalytic performance. This catalyst operates under mild conditions, delivers high amide yields, and is recyclable without significant loss of activity. The ortho-iodide substituent is critical, likely facilitating the reaction through hydrogen-bond interactions in the transition state. Its superior activity compared to non-substituted analogs highlights the importance of tailored electronic and steric properties in boronic acid catalysis.

Technology Process of (2-Iodo-5-methoxyphenyl)boronic acid

There total 5 articles about (2-Iodo-5-methoxyphenyl)boronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

3-methoxyphenylboronic acid (10365-98-7,1107579-37-2) → (2-iodo-5-methoxyphenyl)boronic acid (89694-50-8)

Guidance literature:

With iodine; silver sulfate; In ethanol; at 25 ℃; regioselective reaction;

DOI:10.1021/ol100537x

Reference yield: 70.0%

4-methoxyphenylboronic acid (5720-07-0) → (2-iodo-5-methoxyphenyl)boronic acid (89694-50-8)

Guidance literature:

With iodine; silver sulfate; In ethanol; at 25 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo3013258 DOI:10.1021/jo3013258

Reference yield: 40.0%

3-methoxyphenylboronic acid (10365-98-7,1107579-37-2) → 3-methoxy-1-iodobenzene (766-85-8) + (2-iodo-5-methoxyphenyl)boronic acid (89694-50-8)

Guidance literature:

With iodine; silver sulfate; In acetonitrile; at 25 ℃; for 0.0333333h;

DOI:10.1021/ol100537x

upstream raw materials:

3-methoxyphenylboronic acid

tris(2-iodo-5-methoxy phenyl)boroxine

4-methoxyphenylboronic acid

Downstream raw materials:

tris(2-iodo-5-methoxy phenyl)boroxine

2-iodo-5-hydroxyphenylboronic acid

para-iodoanisole

C₂₄H₂₇BIN₃O₃

Refernces

Direct amidation of carboxylic acids catalyzed by ortho-iodo arylboronic acids: Catalyst optimization, scope, and preliminary mechanistic study supporting a peculiar halogen acceleration effect

10.1021/jo3013258

This research aims to develop a catalytic, direct amidation method using free carboxylic acids and amines, bypassing the need for stoichiometric activation or coupling reagents. The study focuses on optimizing ortho-iodoarylboronic acid catalysts for this reaction, identifying 5-methoxy-2-iodophenylboronic acid (MIBA, 4f) as the most effective catalyst. 5-methoxy-2-iodophenylboronic acid (MIBA, 4f) is identified as the optimal catalyst for direct amidation reactions. It is synthesized through a direct iodination procedure and stands out due to its unique electronic and geometric properties. The methoxy group para to the iodide enhances the electron density on the iodine, which is crucial for the catalytic activity. This catalyst demonstrates superior performance compared to its parent compound, 2-iodophenylboronic acid (4a), by providing higher yields of amide products in shorter reaction times under mild conditions at ambient temperature. It is also recyclable, maintaining its activity upon reuse. The study suggests that the ortho-iodide substituent in 4f plays a key role in the transition state of the amidation process, possibly acting as a hydrogen-bond acceptor. The effectiveness of 4f underscores the importance of specific ring substitution patterns in enhancing catalytic efficiency for direct amidation.