3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)prop-2-EN-1-OL

Base Information

• Chemical Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)prop-2-EN-1-OL
• CAS No.: 167896-48-2
• Molecular Formula: C9H17BO3
• Molecular Weight: 202.05600
• Hs Code.: 2931900090
• European Community (EC) Number: 856-528-4
• Nikkaji Number: J2.681.678E
• Mol file: 167896-48-2.mol

Synonyms:167896-48-2;608534-39-0;(E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol;3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PROP-2-EN-1-OL;(E)-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-2-PROPEN-1-OL;TRANS-3-HYDROXY-1-PROPENYLBORONIC ACID PINACOL ESTER;(2E)-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PROP-2-EN-1-OL;SCHEMBL9999329;SCHEMBL9999332;2-Propen-1-ol, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, (2E)-;CS-0107771;D76735;EN300-7269993;Z1255446940;(2E)-3-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PROP-2-EN-1-OL

Chemical Property of 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)prop-2-EN-1-OL

Chemical Property:

• Boiling Point: 80-90 °C(Press: 0.1 Torr)
• PKA: 14.57±0.10(Predicted)
• PSA: 69.92000
• Density: 0.99±0.1 g/cm3(Predicted)
• LogP: 0.12070
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 184.1270746
• Heavy Atom Count: 13
• Complexity: 195

Purity/Quality:

97% ^*data from raw 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=CCO
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/CO

Technology Process of 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)prop-2-EN-1-OL

There total 8 articles about 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)prop-2-EN-1-OL 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: 84.0%

C15H31BO3Si (1092775-33-1) → (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol (167896-48-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 20 ℃; for 1h;

Reference yield: 82.0%

propargyl alcohol (107-19-7) + bis(pinacol)diborane (73183-34-3) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol + (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol (167896-48-2)

Guidance literature:

With NaOC(CH₃)3; HCl; (1,3-dimesitylimidazolidin-2-yl)copper(I) chloride; In tetrahydrofuran; 1.0 mol% Cu-complex, alkyne, diborane, NaOC(CH3)3, CH3OH-dioxane, HCl THF, -50°C, 21 h, N2 atm.; detected by NMR spectra 93:7 ratio of isomers;

DOI:10.1021/ja2007643

Reference yield: 69.0%

tert-butyl (dimethyl){[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy}silane (114653-19-9) → (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol (167896-48-2)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 0.5h;

DOI:10.1039/c7ob00211d

upstream raw materials:

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

1-trimethylsilyloxy-2-propyne

trimethyl([[(2E)-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy])silane

propargyl alcohol

Downstream raw materials:

1-(4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pent-4-en-1-one

(E)-(2S,3R)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pent-4-en-1-one