4,4,5,5-Tetramethyl-2-(3-methylbut-2-en-2-yl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(3-methylbut-2-en-2-yl)-1,3,2-dioxaborolane
• CAS No.: 219488-99-0
• Molecular Formula: C11H21BO2
• Molecular Weight: 196.09
• European Community (EC) Number: 689-570-5
• DSSTox Substance ID: DTXSID80435992
• Nikkaji Number: J1.187.912H
• Mol file: 219488-99-0.mol

Synonyms:219488-99-0;4,4,5,5-tetramethyl-2-(3-methylbut-2-en-2-yl)-1,3,2-dioxaborolane;2-(1,2-dimethyl-1-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-Dioxaborolane;3-Methyl-2-buten-2-ylboronic acid pinacol ester;starbld0017046;SCHEMBL104386;DTXSID80435992;CS-0311484;FT-0739423;W13782;EN300-1718122;3-Methyl-2-buten-2-ylboronic acid pinacol ester, 95%;Z2466360799;2-(1,2-dimethyl-1-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 4,4,5,5-Tetramethyl-2-(3-methylbut-2-en-2-yl)-1,3,2-dioxaborolane

Chemical Property:

• Refractive Index: n20/D 1.450
• Flash Point: 71℃
• PSA: 18.46000
• Density: 0.888 g/mL at 25 °C
• LogP: 2.97410
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 196.1634601
• Heavy Atom Count: 14
• Complexity: 247

Purity/Quality:

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

3-Methyl-2-buten-2-ylboronic acid pinacol ester 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C(=C(C)C)C

Technology Process of 4,4,5,5-Tetramethyl-2-(3-methylbut-2-en-2-yl)-1,3,2-dioxaborolane

There total 6 articles about 4,4,5,5-Tetramethyl-2-(3-methylbut-2-en-2-yl)-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: 92.0%

2-bromo-3-methylbut-2-ene (3017-70-7) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 2-(1,2-dimethylprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (219488-99-0)

Guidance literature:

2-bromo-3-methylbut-2-ene; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.5h; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; pentane; at -78 - 20 ℃; for 0.75h; Inert atmosphere;

DOI:10.1021/jacs.7b02569

Reference yield: 58.0%

5-bromo-1-methyl-H-indole (10075-52-2) + 2-bromo-3-methylbut-2-ene (3017-70-7) → 2-(1,2-dimethylprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (219488-99-0)

Guidance literature:

5-bromo-1-methyl-H-indole; With potassium methanolate; In 1,2-dimethoxyethane; at 30 ℃; for 0.166667h; Inert atmosphere;

2-bromo-3-methylbut-2-ene; In 1,2-dimethoxyethane; at 30 ℃; for 1h;

DOI:10.1021/ja309578k

Reference yield: 58.0%

→ 2-(1,2-dimethylprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (219488-99-0)

Guidance literature:

With potassium methanolate; In 1,2-dimethoxyethane; at 30 ℃; for 0.166667h; Inert atmosphere;

In 1,2-dimethoxyethane; for 1h;

upstream raw materials:

Dimethylallene

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

2-bromo-3-methylbut-2-ene

5-bromo-1-methyl-H-indole

Refernces

• 1、 -. "An organic boron compound". Paragraph 0072-0074; 0096-0097. . Retrieved 2019/02/20.
• 2、 Yamamoto, Eiji,Izumi, Kiyotaka,Horita, Yuko,Ito, Hajime. "Anomalous reactivity of silylborane: Transition-metal-free boryl substitution of aryl, alkenyl, and alkyl halides with silylborane/alkoxy base systems". supporting information. p. 19997 - 20000. Retrieved 2013/02/23.