4,4,5,5-Tetramethyl-2-(1-propyn-1-YL)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(1-propyn-1-YL)-1,3,2-dioxaborolane
• CAS No.: 347389-75-7
• Molecular Formula: C9H15BO2
• Molecular Weight: 166.028
• Hs Code.: 2931900090
• European Community (EC) Number: 865-614-0
• Nikkaji Number: J1.534.831C
• Mol file: 347389-75-7.mol

Synonyms:347389-75-7;PROP-1-YNYLBORONIC ACID PINACOL ESTER;4,4,5,5-TETRAMETHYL-2-(1-PROPYN-1-YL)-1,3,2-DIOXABOROLANE;4,4,5,5-TETRAMETHYL-2-(PROP-1-YN-1-YL)-1,3,2-DIOXABOROLANE;1-PROPYNEBORONIC ACID PINACOL ESTER;4,4,5,5-tetramethyl-2-prop-1-ynyl-1,3,2-dioxaborolane;MFCD13182123;SCHEMBL14819095;XNA38975;ZB0257;1-Propyn-1-boronic acid pinacol ester;MB12869;BS-28200;SY032333;CS-0175345;A50060;EN300-220354;Z1235967821

Chemical Property of 4,4,5,5-Tetramethyl-2-(1-propyn-1-YL)-1,3,2-dioxaborolane

Chemical Property:

• Boiling Point: 160.656 °C at 760 mmHg
• Flash Point: 50.963 °C
• PSA: 18.46000
• Density: 0.935 g/cm³
• LogP: 1.64110
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 166.1165099
• Heavy Atom Count: 12
• Complexity: 228

Purity/Quality:

98%Min ^*data from raw suppliers

1-PropyneboronicAcidPinacolEster ^*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#CC

Technology Process of 4,4,5,5-Tetramethyl-2-(1-propyn-1-YL)-1,3,2-dioxaborolane

There total 2 articles about 4,4,5,5-Tetramethyl-2-(1-propyn-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: 89.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + prop-1-yne (74-99-7) → 4,4,5,5-tetramethyl-2-(prop-1-yn-1-yl)-1,3,2-dioxaborolane (347389-75-7)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; (N2); addn. dropwise of soln. of n-BuLi/hexanes at -75°C for 0.5 h to stirred soln. of propyne in Et2O; stirring for 1.5 h at -75°C; addn. dropwise soln. of (i-Pr)OBO2C2Me4 in Et2O for 1 h; warming to 20°C for 4 h; stirring for 16 h; addn. of HCl soln. in Et2O at 0°C for 45 min; stirring for 0.5h at 0°C and for 1.5h at 20°C; pptn., filtration, washing with hexane; combining of org. solns., removal of solvent under reduced pressure, fractional distn., elem. anal.;

DOI:10.1021/om700570f

Reference yield:

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 1-propynyl lithium (4529-04-8) → 4,4,5,5-tetramethyl-2-(prop-1-yn-1-yl)-1,3,2-dioxaborolane (347389-75-7)

Guidance literature:

DOI:10.1021/ol050542r

Reference yield: 90.0%

mesitylenecarbonitrile oxide (2904-57-6) + 4,4,5,5-tetramethyl-2-(prop-1-yn-1-yl)-1,3,2-dioxaborolane (347389-75-7) → 5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(2,4,6-trimethylphenyl)isoxazole (374715-18-1)

Guidance literature:

In diethyl ether; for 64h; Heating;

DOI:10.1039/b103319k DOI:10.1016/j.tet.2005.05.015

upstream raw materials:

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

1-propynyl lithium

prop-1-yne

Downstream raw materials:

5-methyl-3-phenyl-4-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)-isoxazole

5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(2,4,6-trimethylphenyl)isoxazole

3-bromo-5-methyl-4-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)-isoxazole

4'-methyl-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-[1,1';2',1'']terphenyl-3',6'-dicarboxylic acid dimethyl ester