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

Base Information

• Chemical Name: 2-(3-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 635305-47-4
• Molecular Formula: C12H16BClO2
• Molecular Weight: 238.522
• Hs Code.: 2934999090
• European Community (EC) Number: 801-626-4
• DSSTox Substance ID: DTXSID90434572
• Nikkaji Number: J2.968.570C
• Wikidata: Q72456615
• Mol file: 635305-47-4.mol

Synonyms:635305-47-4;2-(3-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-CHLOROPHENYLBORONIC ACID, PINACOL ESTER;3-Chlorophenylboronic acid pinacol ester;MFCD05663877;1,3,2-DIOXABOROLANE, 2-(3-CHLOROPHENYL)-4,4,5,5-TETRAMETHYL-;3-CHLOROPHENYLBORONICACID,PINACOLESTER;SCHEMBL797870;DTXSID90434572;CHQKHVZXPNHWEA-UHFFFAOYSA-N;AKOS015960140;AB22002;AS-2620;SY110427;CS-0004330;FT-0600140;EN300-1425828;A868116;Z1336745112;2-(3-Chlorophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Chemical Property of 2-(3-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.506
• Boiling Point: 317.893 °C at 760 mmHg
• Flash Point: 146.057 °C
• PSA: 18.46000
• Density: 1.103 g/cm³
• LogP: 2.63920
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 238.0931876
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

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

3-Chlorophenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC=C2)Cl

Technology Process of 2-(3-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 45 articles about 2-(3-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 98.0%

1-(3-chlorobenzoyl)piperidine-2,6-dione + bis(pinacol)diborane (73183-34-3) → 2-(3-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (635305-47-4)

Guidance literature:

With Wilkinson's catalyst; In toluene; at 160 ℃; for 15h; Inert atmosphere;

DOI:10.1021/acs.joc.0c02157

Reference yield: 95.0%

3-iodochlorobenzene (625-99-0) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 2-(3-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (635305-47-4)

Guidance literature:

With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; hexane; at -60 ℃;

DOI:10.1021/ol2010006

Reference yield: 94.0%

bis(pinacol)diborane (73183-34-3) + 3-chlorobenzoate (535-80-8) → 2-(3-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (635305-47-4)

Guidance literature:

With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane; In 1,4-dioxane; at 160 ℃; for 15h;

DOI:10.1002/anie.201810145

upstream raw materials:

pinacolboronic acid

3-chloro-1-trifluoromethanesulfonyloxybenzene

3-monochlorophenol

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

Downstream raw materials:

methyl 2-(3-chlorophenyl)-2-(4-chlorophenyl)-3-phenylpropanoate

3-monochlorophenol

3-chlorobenzoate

2,3-bis(3-chlorophenyl)quinoxaline

Refernces

• 1、 Du, Linlin,Sun, Li,Zhang, Hua. "Photochemical and electrochemical C-N borylation of arylhydrazines". supporting information. p. 1716 - 1719. Retrieved 2022/02/21.
• 2、 Qiu, Di,Li, Songyi,Yue, Guanglu,Mao, Jinshan,Xu, Bei,Yuan, Xinyu,Ye, Fei. "Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron". supporting information. . Retrieved 2021/11/04.