2-Iodophenylboronic acid

Base Information

• Chemical Name: 2-Iodophenylboronic acid
• CAS No.: 1008106-86-2
• Molecular Formula: C6H6BIO2
• Molecular Weight: 247.828
• Hs Code.: 2931900090
• Mol file: 1008106-86-2.mol

Synonyms:Boronic acid, B-(2-iodophenyl)-;

Chemical Property of 2-Iodophenylboronic acid

Chemical Property:

• Melting Point: 189-194°C
• Boiling Point: 345.3 °C at 760 mmHg
• PKA: 8.29±0.58(Predicted)
• Flash Point: 162.7 °C
• PSA: 40.46000
• Density: 1.95 g/cm³
• LogP: -0.02900
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Iodophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Used to promote greener amidations of carboxylic acids and amines in catalytic amounts. This technology avoids the requirement of preactivation of the carboxylic acid or use of coupling reagents.Direct Amidation of Carboxylic Acids Catalyzed by?ortho-Iodo Arylboronic Acids: Catalyst Optimization, Scope, and Preliminary Mechanistic Study Supporting a Peculiar Halogen Acceleration Effect

Technology Process of 2-Iodophenylboronic acid

There total 3 articles about 2-Iodophenylboronic 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%

hydrogenchloride (7647-01-0,15364-23-5) + 1,2-Diiodobenzene (615-42-9) → ortho-iodophenylboronic acid (1008106-86-2)

Guidance literature:

1,2-Diiodobenzene; With isopropylmagnesium chloride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2h;

With Triisopropyl borate; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃;

hydrogenchloride; In tetrahydrofuran; diethyl ether; water; at 20 ℃; for 0.5h;

DOI:10.1002/anie.200705468

Reference yield: 50.0%

1,2-Diiodobenzene (615-42-9) → ortho-iodophenylboronic acid (1008106-86-2)

Guidance literature:

1,2-Diiodobenzene; With isopropylmagnesium chloride; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

With Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo3013258 DOI:10.1021/jo3013258

Reference yield:

phenylboronic acid (98-80-6) → iodobenzene (591-50-4) + ortho-iodophenylboronic acid (1008106-86-2)

Guidance literature:

With copper(II) nitrate trihydrate; iodine; N,N`-dimethylethylenediamine; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

DOI:10.1016/j.catcom.2012.11.022

upstream raw materials:

hydrogenchloride

1,2-Diiodobenzene

phenylboronic acid

Downstream raw materials:

2-methylbenzo[4,5]imidazo[1,2-a]pyridine

Thiazolo<3,2-a>benzimidazol

2-methylbenzo[4,5]imidazo[2,1-b]thiazole

potassium 2-iodophenyltrifluoroborate

Refernces

• 1、 Gernigon, Nicolas,Al-Zoubi, Raed M.,Hall, Dennis G.. "Direct amidation of carboxylic acids catalyzed by ortho-iodo arylboronic acids: Catalyst optimization, scope, and preliminary mechanistic study supporting a peculiar halogen acceleration effect". . p. 8386 - 8400,15. Retrieved 2012/12/11.
• 2、 Al-Zoubi, Raed M.,Marion, Olivier,Hall, Dennis G.. "Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature". supporting information; experimental part. p. 2876 - 2879. Retrieved 2009/02/06.