CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE

Base Information

• Chemical Name: CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE
• CAS No.: 173603-23-1
• Molecular Formula: C20H30B2O4
• Molecular Weight: 356.078
• Mol file: 173603-23-1.mol

Synonyms:1,3,2-Dioxaborolane,2,2'-(1-phenyl-1,2-ethenediyl)bis[4,4,5,5-tetramethyl-, (E)-;2,2'-[(E)-1-phenylethene-1,2-diyl]bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane);(E)-Phenyl-1,2-ethylenediboronic acid bis(pinacol) ester;

Chemical Property of CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE

Chemical Property:

• Vapor Pressure: 3.65E-05mmHg at 25°C
• Melting Point: 69-73 °C(lit.)
• Refractive Index: 1.498
• Boiling Point: 363.9 °C at 760 mmHg
• Flash Point: 173.9 °C
• PSA: 36.92000
• Density: 1.03 g/cm³
• LogP: 4.33280

Purity/Quality:

99% ^*data from raw suppliers

(E)-Phenyl-1,2-ethylenediboronic acid bis(pinacol) ester 98% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE

There total 6 articles about CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE 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: 93.0%

phenylacetylene (536-74-3) + bis(pinacol)diborane (73183-34-3) → (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1)

Guidance literature:

With gold; In toluene; at 100 ℃; for 1.5h; Reagent/catalyst; Solvent; Time; Concentration; diastereoselective reaction; Catalytic behavior; Green chemistry;

DOI:10.1021/ol4028013

Reference yield:

phenylacetylene (536-74-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane (143825-84-7) + 4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane (78782-27-1) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; tert-butylisonitrile; carbon monoxide; at 50 ℃; under 760.051 Torr;

DOI:10.1016/j.jorganchem.2020.121614

Reference yield:

phenylacetylene (536-74-3) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane (83947-56-2) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1)

Guidance literature:

With triphenylphosphine; In toluene; at 160 ℃; for 1.5h; under 1125.11 Torr; stereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.201002777

upstream raw materials:

phenylacetylene

bis(pinacol)diborane

4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane

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

Downstream raw materials:

(E)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-phenylethene

Triphenylethylene

(E)-2-(2-bromo-1-phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(E)-2-(2-chloro-1-phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Refernces

• 1、 Han, Xiao,Chen, Zheng,Chen, Wenxing,Lv, Chunlin,Ji, Yongjun,Li, Jing,Cheong, Weng-Chon,Lei, Xiaojuan,Peng, Qing,Chen, Chen,Wang, Dingsheng,Lian, Chao,Li, Yadong. "A general strategy to prepare atomically dispersed biomimetic catalysts based on host-guest chemistry". supporting information. p. 1895 - 1898. Retrieved 2021/03/01.
• 2、 Kuang, Zhijie,Gao, Guoliang,Song, Qiuling. "Base-catalyzed diborylation of alkynes: synthesis and applications of cis-1,2-bis(boryl)alkenes". . p. 62 - 66. Retrieved 2018/09/27.