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

Base Information

• Chemical Name: 2-(4-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 195062-61-4
• Molecular Formula: C12H16BClO2
• Molecular Weight: 238.522
• Hs Code.: 2934999090
• European Community (EC) Number: 626-831-4
• DSSTox Substance ID: DTXSID20442807
• Nikkaji Number: J1.255.213K
• Wikidata: Q72456618
• Mol file: 195062-61-4.mol

Synonyms:195062-61-4;4-Chlorophenylboronic acid pinacol ester;2-(4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-CHLOROPHENYLBORONIC ACID, PINACOL ESTER;1,3,2-DIOXABOROLANE, 2-(4-CHLOROPHENYL)-4,4,5,5-TETRAMETHYL-;MFCD05663875;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)chlorobenzene;4-CHLOROPHENYLBORONIC ACID,PINACOL ESTER;SCHEMBL661288;DTXSID20442807;NYARTXMDWRAVIX-UHFFFAOYSA-N;AMY29953;AC1415;AKOS015910480;AB21998;AS-2511;4-chlorophenyl boronic acid pinacol ester;SY025304;4-Chlorobenzeneboronic acid, pinacol ester;C3500;CS-0041642;4-Chlorophenylboronic acid pinacol ester, 97%;EN300-316749;A880158;J-012635;p-Chlorophenylboronic acid 2,3-dimethyl-2,3-butanediyl;Z1336745102;1-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

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

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 50-55 °C(lit.)
• Refractive Index: 1.506
• Boiling Point: 308.678 °C at 760 mmHg
• Flash Point: 140.484 °C
• PSA: 18.46000
• Density: 1.103 g/cm³
• LogP: 2.63920
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 238.0931876
• Heavy Atom Count: 16
• Complexity: 244

Purity/Quality:

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

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

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)Cl
• Uses: 4-Chlorophenylboronic acid pinacol ester can be used as a reagent in Suzuki-Miyaura cross-coupling reaction to form C-C bonds by reacting with different aryl halides over palladium catalysts. It can also be used as a reactant: To prepare 2-(4-chlorophenyl)-4H-chromen-4-one by treating with 4-chromanone via one-pot palladium-catalyzed dehydrogenation and oxidative boron-Heck coupling reaction. In the ligand-enabled C-H bond activation reaction in the presence of a palladium catalyst. To synthesize biaryl amides via Cu-catalyzed C-H bond coupling of aryl arylamides.

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

There total 81 articles about 2-(4-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: 96.0%

1-Chloro-4-iodobenzene (637-87-6) + bis(pinacol)diborane (73183-34-3) → 4-chlorophenylboronic acid pinacol ester (195062-61-4)

Guidance literature:

With copper(l) iodide; palladium diacetate; caesium carbonate; triphenylphosphine; In acetonitrile; at 20 ℃; for 24h; chemoselective reaction;

DOI:10.1002/ejoc.201301634 DOI:10.1002/ejoc.201301634

Reference yield: 95.0%

bromochlorobenzene (106-39-8) + bis(pinacol)diborane (73183-34-3) → 4-chlorophenylboronic acid pinacol ester (195062-61-4)

Guidance literature:

With C₂₆H₂₅Cl₂FeN₂PPd; potassium acetate; In isopropyl alcohol; at 85 ℃; for 6h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.organomet.9b00398

Reference yield: 92.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-Chlorophenylboronic acid (1679-18-1) → 4-chlorophenylboronic acid pinacol ester (195062-61-4)

Guidance literature:

With magnesium sulfate; In diethyl ether; at 20 ℃; for 16h; Inert atmosphere; Schlenk technique;

DOI:10.1055/s-0035-1562447

upstream raw materials:

bromochlorobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

1-Chloro-4-iodobenzene

chlorobenzene

Downstream raw materials:

2-(2-bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(3-bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(4-chloro-phenyl)-carbamic acid methyl ester

diethyl (4-chlorophenyl)phosphonate

Refernces

• 1、 Hu, Jiefeng,Huang, Mingming,Marder, Todd B.,Radius, Udo,Tang, Man,Westcott, Stephen A.. "Cu-mediated: vs. Cu-free selective borylation of aryl alkyl sulfones". supporting information. p. 395 - 398. Retrieved 2022/01/19.
• 2、 Chen, Zicong,Ng, Shan Shan,So, Chau Ming,Yuen, On Ying. "Palladium-Catalyzed Chemoselective Borylation of (Poly)halogenated Aryl Triflates and Their Application in Consecutive Reactions". . . Retrieved 2022/03/15.