4,4,5,5-Tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane
• CAS No.: 865350-17-0
• Molecular Formula: C9H15 B O2
• Molecular Weight: 166.028
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID30470474
• Nikkaji Number: J1.793.255A
• Mol file: 865350-17-0.mol

Synonyms:865350-17-0;Allenylboronic acid pinacol ester;4,4,5,5-Tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane;2-Allenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD09265121;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(1,2-propadienyl)-;2-Allenyl-4,4,5,5-tetramethyl(1,3,2)-dioxaborolane;SCHEMBL14725364;AMY1622;DTXSID30470474;4,4,5,5-Tetramethyl-2-(1,2-propadienyl)-1,3,2-dioxaborolane;AKOS015893166;FS-5745;Allenylboronic acid pinacol ester, 97%;1,2-Propadieneboronic Acid Pinacol Ester;SY057276;CS-0109519;S10937

Chemical Property of 4,4,5,5-Tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 2.759mmHg at 25°C
• Refractive Index: n20/D 1.459
• Boiling Point: 81 °C / 18.6mmHg
• Flash Point: 66 °C
• PSA: 18.46000
• Density: 0.94
• LogP: 1.95890
• Storage Temp.: Refrigerator
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 166.1165099
• Heavy Atom Count: 12
• Complexity: 211

Purity/Quality:

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

Allenylboronic acid pinacol ester ^*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

Technology Process of 4,4,5,5-Tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane

There total 5 articles about 4,4,5,5-Tetramethyl-2-(propa-1,2-dien-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: 60.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + potassium trifluoro(propa-1,2-dien-1-yl)borate → 4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane (865350-17-0)

Guidance literature:

With montmorillonite K₁₀; In tetrahydrofuran; at 25 ℃; Molecular sieve;

DOI:10.21577/0103-5053.20180126

Reference yield: 60.0%

2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (70557-99-2) + acetylenemagnesium bromide (4301-14-8) → 4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane (865350-17-0) + 4,4,5,5-tetramethyl-2-(prop-2-yn-1-yl)-1,3,2-dioxaborolane (1337935-39-3)

Guidance literature:

In tetrahydrofuran; at -78 - -65 ℃; Inert atmosphere;

DOI:10.1021/ol202343c

Reference yield: 54.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + propargyl bromide (106-96-7) → 4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane (865350-17-0)

Guidance literature:

propargyl bromide; With magnesium; mercury dichloride; In diethyl ether; toluene; at 5 ℃; Inert atmosphere;

With Trimethyl borate; In diethyl ether; toluene; at -78 - 0 ℃; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; Further stages;

DOI:10.1016/j.tet.2009.10.002

upstream raw materials:

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

allenyl boronic acid

propargyl bromide

2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

4-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-p-tolyl-allyl]-morpholine