4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROVINYLOXY-PHENYL)-[1,3,2]DIOXABOROLANE

Base Information

• Chemical Name: 4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROVINYLOXY-PHENYL)-[1,3,2]DIOXABOROLANE
• CAS No.: 865485-85-4
• Molecular Formula: C₁₄H₁₆BF₃O₃
• Molecular Weight: 300.085
• Mol file: 865485-85-4.mol

Synonyms:4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROVINYLOXY-PHENYL)-[1,3,2]DIOXABOROLANE;1,3,2-DIOXABOROLANE,4,4,5,5-TETRAMETHYL-2-[4-[(1,2,2-TRIFLUOROETHENYL)OXY]PHENYL]-

Chemical Property of 4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROVINYLOXY-PHENYL)-[1,3,2]DIOXABOROLANE

Chemical Property:

• Boiling Point: 304.3±42.0 °C(Predicted)
• PSA: 27.69000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 3.39970

Purity/Quality:

4,4,5,5-Tetramethyl-2-(4-trifluorovinyloxy-phenyl)-[1,3,2]dioxaborolane 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROVINYLOXY-PHENYL)-[1,3,2]DIOXABOROLANE

There total 3 articles about 4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROVINYLOXY-PHENYL)-[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: 55.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 1-bromo-4-(trifluorovinyloxy)benzene (134151-77-2) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-phenyl trifluorovinyl ether (865485-85-4)

Guidance literature:

1-bromo-4-(trifluorovinyloxy)benzene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 1h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In diethyl ether; pentane; at 20 ℃; for 1h;

DOI:10.1021/ol061642f

Reference yield:

4-bromo-phenol (106-41-2) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-phenyl trifluorovinyl ether (865485-85-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium hydroxide / dimethyl sulfoxide / 24 h / 30 - 150 °C

2.1: zinc / acetonitrile / 18 h / 80 °C

3.1: tert.-butyl lithium / diethyl ether / -80 °C

3.2: 20 °C

With tert.-butyl lithium; potassium hydroxide; zinc; In diethyl ether; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/cm203539m

Reference yield:

1-bromo-4-(2-bromo-1,1,2,2-tetrafluoroethoxy)benzene (113939-45-0) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-phenyl trifluorovinyl ether (865485-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: zinc / acetonitrile / 18 h / 80 °C

2.1: tert.-butyl lithium / diethyl ether / -80 °C

2.2: 20 °C

With tert.-butyl lithium; zinc; In diethyl ether; acetonitrile;

DOI:10.1021/cm203539m

upstream raw materials:

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

1-bromo-4-(trifluorovinyloxy)benzene

4-bromo-phenol

1-bromo-4-(2-bromo-1,1,2,2-tetrafluoroethoxy)benzene

Refernces

• 1、 Lim, Bogyu,Hwang, Jin-Taek,Jin, Young Kim,Ghim, Jieun,Vak, Doojin,Noh, Yong-Young,Lee, Soo-Hyoung,Lee, Kwanghee,Heeger, Alan J.,Kim, Dong-Yu. "Synthesis of a new cross-linkable perfluorocyclobutane-based hole-transport material". . p. 4703 - 4706. Retrieved 2007/10/03.