4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane

Base Information

• Chemical Name: 4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane
• CAS No.: 4627-10-5
• Molecular Formula: C8H15 B O2
• Molecular Weight: 154.017
• Hs Code.: 29349990
• European Community (EC) Number: 225-039-2
• DSSTox Substance ID: DTXSID90963534
• Nikkaji Number: J265.526H
• Mol file: 4627-10-5.mol

Synonyms:4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane

Chemical Property of 4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane

Chemical Property:

• Vapor Pressure: 6.4mmHg at 25°C
• Refractive Index: n 20/D 1.429
• Boiling Point: 144.5°Cat760mmHg
• Flash Point: 41.2°C
• PSA: 18.46000
• Density: 0.88g/cm³
• LogP: 1.80380
• Storage Temp.: Refrigerator (+4°C)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 154.1165099
• Heavy Atom Count: 11
• Complexity: 156

Purity/Quality:

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

Vinylboronic acid 2-methyl-2,4-pentanediol ester contains phenothiazine as stabilizer, 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 10-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of 4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane

There total 8 articles about 4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane 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: 82.0%

2-methyl-2,4-pentanediol (107-41-5) + vinyl magnesium bromide (1826-67-1) → 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane (4627-10-5)

Guidance literature:

vinyl magnesium bromide; With Trimethyl borate; In tetrahydrofuran; at -78 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 0.166667h;

2-methyl-2,4-pentanediol; In tetrahydrofuran; diethyl ether; at 20 ℃; for 1h;

DOI:10.1039/b507900d

Reference yield: 82.0%

2-methyl-2,4-pentanediol (107-41-5) + Trimethyl borate (121-43-7,63156-11-6) + vinyl magnesium bromide (1826-67-1) → 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane (4627-10-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; diethyl ether; under Ar; soln. CH2CHMgBr in THF added dropwise over 1 h to stirred soln. of anhyd. B(OMe)3 in THF at -78°C; stirred for 1 h; warmed to room temp.; 20% HCl added; 10 min; soln. of diol in Et2O added; stirred for 1 h; two phases sepd.; aq. phase extd. with Et2O; combined org. extracts washed with satd. aq. NaHCO3 and water; dried (MgSO4); solvent evapd.; purified by Kugelroehr distn.;

DOI:10.1039/b507900d

Reference yield: 30.0%

4,4,4',4',6,6'-hexamethyl-2,2'-bi(1,3,2-dioxaborinane)bis(hexyleneglycolato)diboron (230299-21-5) + pinacol vinylboronate (75927-49-0) → 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane (4627-10-5)

Guidance literature:

In methanol; at 90 ℃; for 16h; Schlenk technique; Inert atmosphere;

DOI:10.1039/d1cc05815k

upstream raw materials:

2-butoxy-4,4,6-trimethyl-[1,3,2]dioxaborinane

vinylmagnesium chloride

2-ethynyl-4,4,6-trimethyl-[1,3,2]dioxaborinane

2-methyl-2,4-pentanediol

Downstream raw materials:

2-vinylpyridine

2-(2-triphenylstannylethyl)-4,4,6-trimethyl-1,3,2-dioxaborinan

C₂₀H₁₇F₄N₃O

C₁₉H₁₉NO₂

Refernces

• 1、 Praveenganesh, Nageswaran,De Candia, Cristina,Memboeuf, Antony,Lendvay, Gy?rgy,Gimbert, Yves,Chavant, Pierre Y.. "Improved dimethylzinc-promoted vinylation of nitrones with vinylboronic esters". scheme or table. p. 2447 - 2454. Retrieved 2010/11/05.
• 2、 Lightfoot, Andrew P.,Maw, Graham,Thirsk, Carl,Twiddle, Steven J. R.,Whiting, Andrew. "4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane: A superior 2-carbon building block for vinylboronate Heck couplings". . p. 7645 - 7648. Retrieved 2007/10/03.