4,4,5,5-Tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane
• CAS No.: 143825-84-7
• Molecular Formula: C14H19BO2
• Molecular Weight: 230.115
• Hs Code.: 2934999090
• European Community (EC) Number: 811-909-4
• DSSTox Substance ID: DTXSID20452643
• Nikkaji Number: J672.986J
• Wikidata: Q82273400
• Mol file: 143825-84-7.mol

Synonyms:143825-84-7;4,4,5,5-Tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane;1-Phenylvinylboronic acid, pinacol ester;4,4,5,5-tetramethyl-2-(1-phenylethenyl)-1,3,2-dioxaborolane;1-Phenylvinylboronic acid pinacol ester;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(1-phenylethenyl)-;2-(1-Phenylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;SCHEMBL3555946;DTXSID20452643;RMGBWPMWUZSIMH-UHFFFAOYSA-N;MFCD06659923;AKOS016844869;1-Phenylvinylboronic acid,pinacol ester;AB26646;AS-55246;CS-0099710;FT-0688878;1-Phenylvinylboronic acid pinacol ester, 96%;EN300-213139;H11770;Z2044805724;2-(1-Phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,3,2-Dioxaborolane,4,4,5,5-tetramethyl-2-(1-phenylethenyl)-

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

Chemical Property:

• Vapor Pressure: 0.008mmHg at 25°C
• Melting Point: 42-49 °C
• Refractive Index: 1.497
• Boiling Point: 277.336 °C at 760 mmHg
• Flash Point: 121.529 °C
• PSA: 18.46000
• Density: 0.987 g/cm³
• LogP: 3.33120
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 230.1478100
• Heavy Atom Count: 17
• Complexity: 287

Purity/Quality:

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

1-Phenylvinylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C(=C)C2=CC=CC=C2

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

There total 34 articles about 4,4,5,5-Tetramethyl-2-(1-phenylvinyl)-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: 99.0%

1-phenyl vinyl triflate (28143-79-5) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane (143825-84-7)

Guidance literature:

With triphenylphosphine; bis(triphenylphosphine)palladium(II) chloride; In toluene; mixt. in toluene stirred at 50°C for 4 h; treated (H2O) at room temp.; extd. (benzene); washed with brine; dried (MgSO4); purified by chromy. on silica gel or by distn. (vac.);

DOI:10.1021/ja0202255

Reference yield: 98.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + phenylvinylboronic acid (14900-39-1) → 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane (143825-84-7)

Guidance literature:

With magnesium sulfate; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.6b01446

Reference yield: 96.0%

phenylacetylene (536-74-3) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane (143825-84-7)

Guidance literature:

bis(pinacol)diborane; With C₂₉H₃₉ClCuN; sodium t-butanolate; In tetrahydrofuran; at 22 ℃; for 0.0833333h; Inert atmosphere;

phenylacetylene; In tetrahydrofuran; methanol; at 22 ℃; for 12h; Reagent/catalyst; Inert atmosphere;

DOI:10.1002/anie.202106107

upstream raw materials:

1-bromovinylbenzene

bis(pinacol)diborane

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

phenylacetylene

Downstream raw materials:

2-(2,2-difluoro-1-phenylcyclopropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-chloro-5,7-difluoro-3-methyl-2-(1-phenylvinyl)quinoline

acetophenone

phenol

Refernces

• 1、 Braconi, Elena,Cramer, Nicolai. "A Chiral Naphthyridine Diimine Ligand Enables Nickel-Catalyzed Asymmetric Alkylidenecyclopropanations". . p. 16425 - 16429. Retrieved 2020.
• 2、 Chen, Jieping,Shen, Xuzhong,Lu, Zhan. "Cobalt-Catalyzed Markovnikov-Type Selective Hydroboration of Terminal Alkynes". supporting information. p. 690 - 694. Retrieved 2020/11/30.
• 3、 Lai, Qingheng,Ozerov, Oleg V.. "Dehydrogenative Diboration of Alkynes Catalyzed by Ir/CO/tBuNC System". . . Retrieved 2020/11/30.