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

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane
• CAS No.: 126689-00-7
• Molecular Formula: C10H19BO2
• Molecular Weight: 182.071
• Hs Code.: 2934999090
• European Community (EC) Number: 801-924-4
• DSSTox Substance ID: DTXSID50569071
• Nikkaji Number: J396.327F
• Mol file: 126689-00-7.mol

Synonyms:126689-00-7;4,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane;2,2-DIMETHYLETHENYLBORONIC ACID PINACOL ESTER;2-Methylprop-1-enylboronic acid pinacol ester;2-Methyl-1-propenylboronic acid pinacol ester;4,4,5,5-TETRAMETHYL-2-(2-METHYLPROP-1-ENYL)-1,3,2-DIOXABOROLANE;4,4,5,5-Tetramethyl-2-(2-methyl-1-propenyl)-1,3,2-dioxaborolane;MFCD09842762;1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-(2-METHYL-1-PROPEN-1-YL)-;LWXHOCHDERDUID-UHFFFAOYSA-N;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(2-methyl-1-propenyl)-;SCHEMBL115787;DTXSID50569071;(2-METHYLPROP-1-EN-1-YL)BORONIC ACID PINACOL ESTER;4,4,5,5-tetramethyl-2-(2-methyl-propenyl)-[1,3,2]dioxaborolane;AKOS016000184;AB53739;CS-W003667;AM803126;AS-18690;SY026551;T3469;2-methyl-1-propenyl boronic acid pinacol ester;EN300-260121;(2-Methyl-1-propenyl)boronic Acid Pinacol Ester;A889384;2-Methyl-1-propenylboronic acid pinacol ester, 97%;J-005421;Z1255403604

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

Chemical Property:

• Refractive Index: n20/D 1.4422
• Boiling Point: 71°C/19mmHg(lit.)
• Flash Point: 66oC
• PSA: 18.46000
• Density: 0.8879 g/mL at 25oC
• LogP: 2.58400
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 182.1478100
• Heavy Atom Count: 13
• Complexity: 211

Purity/Quality:

98% ^*data from raw suppliers

2,2-Dimethylethenylboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C=C(C)C
• Uses: 2,2-Dimethylethenylboronic acid pinacol ester

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

There total 4 articles about 4,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-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: 81.0%

(2-Methyl-1-propenyl)-nonafluorbutansulfonat (84224-48-6) + bis(pinacol)diborane (73183-34-3) → 2-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-propene (126689-00-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine; In toluene; at 70 ℃; for 72h; Inert atmosphere; Sealed vessel;

DOI:10.3762/bjoc.6.141

Reference yield: 73.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 2-methylpropen-1-ylmagnesium bromide (38614-36-7) → 2-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-propene (126689-00-7)

Guidance literature:

In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/jacs.7b01774

Reference yield: 57.0%

2-methyl-1-propenylbromide (3017-69-4) + bis(pinacol)diborane (73183-34-3) → 2-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-propene (126689-00-7)

Guidance literature:

With triphenylphosphine; bis(triphenylphosphine)palladium(II) chloride; In toluene; mixt. in toluene stirred at 50°C for 5 h; treated (H2O) at room temp.; extd. (benzene); washed with brine; dried (MgSO4); purified by chromy. on silica gel or by distn. (vac.);

DOI:10.1021/ja0202255

upstream raw materials:

2-methyl-1-propenylbromide

bis(pinacol)diborane

(2-Methyl-1-propenyl)-nonafluorbutansulfonat

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

Downstream raw materials:

methyl 2-[2-(2-methylpropen-1-yl)benzyl]-4-oxopentanoate

methyl 4-amino-3-(2-methylprop-1-enyl) benzoate

(±)-1-(4-chlorophenyl)-3-methylbut-3-en-1-ol

methyl 5-chloro-3-methoxy-2-(2-methylprop-1-en-1-yl)benzoate