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

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(4-methylpent-3-en-1-yl)-1,3,2-dioxaborolane
• CAS No.: 1073354-67-2
• Molecular Formula: C12H25BO3
• Molecular Weight: 228.1361
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID30592362
• Mol file: 1073354-67-2.mol

Synonyms:1073354-67-2;4,4,5,5-tetramethyl-2-(4-methylpent-3-en-1-yl)-1,3,2-dioxaborolane;4-Methyl-3-pentenylboronic acid pinacol ester;2-METHYLPENT-2-ENE-5-BORONIC ACID PINACOL ESTER;4,4,5,5-tetramethyl-2-(4-methylpent-3-enyl)-1,3,2-dioxaborolane;MFCD08741439;2-Methyl(pent-2-en-5-yl)boronic acid, pinacol ester;DTXSID30592362;AKOS005254986;DB-338629;G63945;EN300-4324251;2-Methylpent-2-ene-5-boronic acid, pinacol ester;2-METHYLPENT-2-ENE-5-BORONICACIDPINACOLESTER;4-Methyl-3-pentenylboronic acid pinacol ester, 97%;J-001847;4,4,5,5-Tetramethyl-2-(4-methyl-3-penten-1-yl)-1,3,2-dioxaborolane

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

Chemical Property:

• Refractive Index: n20/D 1.441
• Boiling Point: 219-223 °C/760 mmHg
• Flash Point: 85 °C
• PSA: 18.46000
• Density: 0.881 g/mL at 25 °C
• LogP: 3.43490
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 210.1791101
• Heavy Atom Count: 15
• Complexity: 236

Purity/Quality:

97% ^*data from raw suppliers

2-METHYLPENT-2-ENE-5-BORONIC ACID PINACOL ESTER 95.00% ^*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)CCC=C(C)C
• Uses: 4,4,5,5-Tetramethyl-2-(4-methyl-3-penten-1-yl)-1,3,2-dioxaborolane helps in developing enantiospecific coupling of secondary and tertiary Boronic esters with aromatic compounds.

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

There total 8 articles about 4,4,5,5-Tetramethyl-2-(4-methylpent-3-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: 72.0%

diethyl (3-methylbut-2-en-1-yl) phosphate (64135-15-5) + 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9) → 4,4,5,5-tetramethyl-2-(4-methylpent-3-en-1-yl)-1,3,2-dioxaborolane (1073354-67-2) + 2-(2,2-dimethylbut-3-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Guidance literature:

4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane; With lithium methanolate; copper(l) chloride; 1-((1S)-2-hydroxy-1-methyl-ethyl)-3-(2,4,6-trimethyl-phenyl)-4,5-dihydro-3H-imidazol-1-ium hexafluorophosphate; In 1,4-dioxane; at 60 ℃; for 0.166667h; Schlenk technique; Inert atmosphere;

diethyl (3-methylbut-2-en-1-yl) phosphate; In 1,4-dioxane; at 60 ℃; for 24h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03692

Reference yield: 60.0%

1-bromo-4-methylpent-3-ene (2270-59-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-(4-methylpent-3-en-1-yl)-1,3,2-dioxaborolane (1073354-67-2)

Guidance literature:

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; With bis(cyclopentadienyl)titanium dichloride; lithium methanolate; In tert-butyl methyl ether; for 0.5h; Inert atmosphere; Glovebox;

1-bromo-4-methylpent-3-ene; In tert-butyl methyl ether; at 60 ℃; for 24h; Sealed tube;

DOI:10.1002/anie.202100569

Reference yield: 60.0%

1-bromo-4-methylpent-3-ene (2270-59-9) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 4,4,5,5-tetramethyl-2-(4-methylpent-3-en-1-yl)-1,3,2-dioxaborolane (1073354-67-2)

Guidance literature:

1-bromo-4-methylpent-3-ene; With magnesium; In tetrahydrofuran; for 4h; Inert atmosphere; Reflux;

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

DOI:10.1039/c2cc32176a

upstream raw materials:

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

4-methyl-3-pentenylmagnesium bromide

1-bromo-4-methylpent-3-ene

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

[(1R)-1,5-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-4-en-1-yl](dimethyl)phenylsilane

(S)-4-(3,7-dimethylocta-1,6-dien-3-yl)phenol

(S)-curcumene