(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE

Base Information

• Chemical Name: (4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE
• CAS No.: 24388-23-6
• Molecular Formula: C12H17BO2
• Molecular Weight: 204.077
• Hs Code.: 29319090
• Mol file: 24388-23-6.mol

Synonyms:Benzeneboronicacid, cyclic tetramethylethylene ester (7CI,8CI);2,3-Butanediol,2,3-dimethyl-, cyclic benzeneboronate (8CI);(Pinacolboryl)benzene;2-Phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Phenylboronic acid pinacolester;Pinacol phenylboronate;Phenylboronic acid pinacol ester;

Chemical Property of (4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE

Chemical Property:

• Vapor Pressure: 0.00586mmHg at 25°C
• Melting Point: 27-31 °C(lit.)
• Refractive Index: 1.49
• Boiling Point: 282.058 °C at 760 mmHg
• Flash Point: 124.384 °C
• PSA: 18.46000
• Density: 0.99 g/cm³
• LogP: 1.98580
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

98% ^*data from raw suppliers

Phenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Phenylboronic acid pinacol ester can be used:To prepare sulfinamide derivatives by reacting with diethylaminosulfur trifluoride (DAST) and potassium phenyltrifluoroborate.As a substrate in the study of Suzuki–Miyaura coupling of various aryl iodides over SiliaCat?Pd(0). suzuki reaction

Technology Process of (4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE

There total 358 articles about (4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE 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: 100.0%

bromobenzene (108-86-1,52753-63-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 85 ℃; for 6h; Inert atmosphere;

Reference yield: 100.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + phenylboronic acid (98-80-6) → 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6)

Guidance literature:

at 0 ℃; for 1h;

DOI:10.1002/chem.200304793

Reference yield: 99.0%

chlorobenzene (108-90-7) + bis(pinacol)diborane (73183-34-3) → 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; triphenylphosphine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In methanol; at 20 - 50 ℃; Product distribution / selectivity; Inert atmosphere;

upstream raw materials:

triphenylboroxine

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

diphenyldiboronic acid

dimethyl phenylboronate

Downstream raw materials:

5,5′-diphenyl-2,2′-bithiophene

5,5-diphenyl-2,2':5',2-terthiophene

N-benzoyl-2-methylaniline

N-phenyl benzoyl amide

Refernces

• 1、 Tagata, Tsuyoshi,Nishida, Mayumi,Nishida, Atsushi. "Continuous-Flow C-H borylation of arene derivatives". . p. 1662 - 1666. Retrieved 2010.
• 2、 Oeschger, Raphael J.,Larsen, Matthew A.,Bismuto, Alessandro,Hartwig, John F.. "Origin of the Difference in Reactivity between Ir Catalysts for the Borylation of C-H Bonds". . p. 16479 - 16485. Retrieved 2019.
• 3、 Gao, Liuzhou,Li, Shuhua,Liu, Xueting,Wang, Guoqiang,Zhang, Hanyin. "Mechanistic insights into the dearomative diborylation of pyrazines: A radical or non-radical process?". . p. 6982 - 6990. Retrieved 2021.
• 4、 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.
• 5、 García Manche?o, Olga,Kuhlmann, Jan H.,Uygur, Mustafa. "Protodesilylation of Arylsilanes by Visible-Light Photocatalysis". supporting information. p. 1689 - 1694. Retrieved 2022/03/14.