2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane
• CAS No.: 94242-85-0
• Molecular Formula: C7H15BO2
• Molecular Weight: 142.006
• Hs Code.: 2934999090
• European Community (EC) Number: 689-046-6
• DSSTox Substance ID: DTXSID00471933
• Nikkaji Number: J1.364.447K,J3.564.400H
• Wikidata: Q72499871
• Mol file: 94242-85-0.mol

Synonyms:94242-85-0;2,4,4,5,5-pentamethyl-1,3,2-dioxaborolane;Methylboronic acid pinacol ester;Methyl boronic acid pinacol ester;C7H15BO2;PENTAMETHYL-1,3,2-DIOXABOROLANE;MFCD09027082;1,3,2-Dioxaborolane, 2,4,4,5,5-pentamethyl-;SCHEMBL14399;DTXSID00471933;AKOS006343549;CS-W018635;DS-2394;MB06754;AC-33927;SY025061;FT-0658154;P2602;EN300-316299;2-methyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane

Chemical Property:

• Refractive Index: 1.4003 (20℃)
• Boiling Point: 120-122℃ (747 Torr)
• Flash Point: 31.3±18.7℃
• PSA: 18.46000
• Density: 0.88±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 1.70840
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 142.1165099
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

98% ^*data from raw suppliers

Methylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C
• Uses: suzuki reaction 2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane is a coupling reagent used in the stereoselective synthesis of spirocyclic ketones.

Technology Process of 2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane

There total 15 articles about 2,4,4,5,5-Pentamethyl-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: 72.0%

bis(pinacol)diborane (73183-34-3) + 5-bromo-1,2-dimethyl-1H-indole → 5-bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (1192037-87-8) + 2,4,4,5,5-pentamethyl-[1,3,2]dioxaborolane (94242-85-0)

Guidance literature:

bis(pinacol)diborane; 5-bromo-1,2-dimethyl-1H-indole; With Trimethyl borate; triethylamine; In octane; at 160 ℃; for 48h;

With hydrogenchloride; In water; for 0.5h; regioselective reaction;

DOI:10.1039/d1sc04487g

Reference yield: 67.0%

1-benzyl-2-methyl-1H-indole (17901-58-5) + bis(pinacol)diborane (73183-34-3) → 1-benzyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + 2,4,4,5,5-pentamethyl-[1,3,2]dioxaborolane (94242-85-0)

Guidance literature:

1-benzyl-2-methyl-1H-indole; bis(pinacol)diborane; With Trimethyl borate; triethylamine; In octane; at 160 ℃; for 48h;

With hydrogenchloride; In water; for 0.5h; regioselective reaction;

DOI:10.1039/d1sc04487g

Reference yield: 67.0%

C16H15N + bis(pinacol)diborane (73183-34-3) → 5-phenyl-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + 2,4,4,5,5-pentamethyl-[1,3,2]dioxaborolane (94242-85-0)

Guidance literature:

C₁₆H₁₅N; bis(pinacol)diborane; With Trimethyl borate; triethylamine; In octane; at 160 ℃; for 48h;

With hydrogenchloride; In water; for 0.5h; regioselective reaction;

DOI:10.1039/d1sc04487g

upstream raw materials:

methane

bis(pinacol)diborane

Cyclopentane

cyclohexane

Downstream raw materials:

(R)-4,4,5,5-tetramethyl-2-(2-phenylbutan-2-yl)-1,3,2-dioxaborolane

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

dihydroxy-methyl-borane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Refernces

• 1、 Chen, Quan,Jiang, Jiachen,Wang, Li,Wu, Aizhen,Yin, Youzhi,Zhang, Hua,Zhang, Ke,Zhao, Mengzhen,Zhong, Qi,Zou, Youliang. "Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation". . p. 15104 - 15109. Retrieved 2021/12/09.
• 2、 Chen, Qi,Dong, Anwang,Wang, Dongxu,Qiu, Lu,Ma, Chunxin,Yuan, Yihui,Zhao, Yunpeng,Jia, Na,Guo, Zhanhu,Wang, Ning. "Efficient and Selective Methane Borylation Through Pore Size Tuning of Hybrid Porous Organic-Polymer-Based Iridium Catalysts". supporting information. p. 10671 - 10676. Retrieved 2019/07/04.