4-CHLOROCARBONYLPHENYLBORONIC ACID PROPANEDIOL ESTER

Base Information

• Chemical Name: 4-CHLOROCARBONYLPHENYLBORONIC ACID PROPANEDIOL ESTER
• CAS No.: 380499-68-3
• Molecular Formula: C13H16BClO3
• Molecular Weight: 266.532
• Mol file: 380499-68-3.mol

Synonyms:4-(CHLOROCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chloride;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoyl chloride;

Chemical Property of 4-CHLOROCARBONYLPHENYLBORONIC ACID PROPANEDIOL ESTER

Chemical Property:

• Boiling Point: 353.3±25.0 °C(Predicted)
• PSA: 35.53000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: 2.36480

Purity/Quality:

98.5% ^*data from raw suppliers

4-Chlorocarbonylphenylboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-CHLOROCARBONYLPHENYLBORONIC ACID PROPANEDIOL ESTER

There total 5 articles about 4-CHLOROCARBONYLPHENYLBORONIC ACID PROPANEDIOL ESTER 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:

4-carboxyphenylboronic acid pinacol ester (180516-87-4) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid chloride (380499-68-3)

Guidance literature:

With thionyl chloride; for 2h; Heating;

DOI:10.1002/chem.200500619

Reference yield:

oxalyl dichloride (79-37-8) + 4-carboxyphenylboronic acid pinacol ester (180516-87-4) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid chloride (380499-68-3)

Guidance literature:

In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 2.33333h;

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid chloride (380499-68-3)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 2 h / Heating / reflux

2: thionyl chloride / N,N-dimethyl-formamide / 2 h / Heating / reflux

With thionyl chloride; N,N-dimethyl-formamide; In toluene;

upstream raw materials:

4-carboxyphenylboronic acid pinacol ester

oxalyl dichloride

thionyl chloride

2,3-dimethyl-2,3-butane diol

Downstream raw materials:

N-neopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

5-(4-dimethylaminophenyl)-2-[4-(dihydroxyboranyl)phenyl]oxazole

N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzamide

4-(4,4,5,5-tetramethyl-[1,2,3]-dioxaborolan-2-yl)-N-(tetrahydropyran-4-yl)-benzamide

Refernces

• 1、 -. "Aminonorbornane derivative and preparation method and application thereof". Paragraph 0088-0092. . Retrieved 2020/04/17.
• 2、 Sargent, Brendon T.,Alexanian, Erik J.. "Cobalt-Catalyzed Aminocarbonylation of Alkyl Tosylates: Stereospecific Synthesis of Amides". supporting information. p. 9533 - 9536. Retrieved 2019/06/24.