4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane
• CAS No.: 75927-49-0
• Molecular Formula: C8H15BO2
• Molecular Weight: 154.017
• Hs Code.: 29319090
• European Community (EC) Number: 629-384-3
• DSSTox Substance ID: DTXSID60997301
• Nikkaji Number: J396.320I
• Wikidata: Q72499875
• Mol file: 75927-49-0.mol

Synonyms:75927-49-0;Vinylboronic acid pinacol ester;4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane;2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-VINYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-Vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaoborolane;MFCD00192492;4,4,5,5-tetramethyl-2-vinyl-[1,3,2]dioxaborolane;2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,3,2-Dioxaborolane, 2-ethenyl-4,4,5,5-tetramethyl-;vinyl boronic acid pinacol ester;Pinacolvinylboronate;Vinylboronic acid pinacol cyclic ester;Pinacol vinylboronate, stabilized with 0.1% BHT;SCHEMBL13544;vinylboronic acid pinacolester;ethenylboronic acid pinacol ester;vinyl-boronic acid pinacol ester;DTXSID60997301;DPGSPRJLAZGUBQ-UHFFFAOYSA-N;ethenyl boronic acid pinacol ester;AKOS004119257;AB04655;CS-W000965;AS-11407;FT-0656065;T2297;EN300-92920;4,4,5,5-tetramethyl-2-vinyl-1,3,2dioxaborolan;vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolan;4,4,5,5-tetramethyl-2-vinyl-1,3,2 dioxaborolane;2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolan;4,4,5,5-tetramethyl-2-vinyl-[1.3.2]dioxaborolane;4,4,5,5-tetramethyl-2-vinyl-1,3,2- dioxaborolane;2-ethenyl-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane;Z1255383363;Vinylboronic acid pinacol ester, stabilized with Phenothiazine;Vinylboronic acid pinacol ester, contains phenothiazine as stabilizer, 95%

Chemical Property of 4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane

Chemical Property:

• Appearance/Colour: Clear colorless to amber liquid
• Refractive Index: n20/D 1.4300(lit.)
• Boiling Point: 131.598 °C at 760 mmHg
• Flash Point: 33.39 °C
• PSA: 18.46000
• Density: 0.89 g/cm³
• LogP: 1.80380
• Storage Temp.: Refrigerator
• Sensitive.: Air Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 154.1165099
• Heavy Atom Count: 11
• Complexity: 159

Purity/Quality:

99%min ^*data from raw suppliers

Pinacol vinylboronate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: Xi
• Statements: 10-43
• Safety Statements: 16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C=C
• Uses: suzuki reaction Reagent used forSuzuki-Miyaura coupling reactionsMizoroki-Heck reactions (cascade reaction)Intramolecular Nozaki-Hiyama-Kishi reactionsStereoselective Cu-catalyzed γ-selective and stereospecific couplingControl of stereoselectivity and mechanistic portrait on intramolecular (4+1)-cycloaddition of dialkoxycarbenesRegio- and stereoselective synthesis of trisubstituted alkenes via gold(I)-catalyzed hydrophosphoryloxylation of haloalkynes followed by Pd-catalyzed consecutive cross-coupling reactionsAsymmetric Birch reductive alkylationReagent used in Preparation of Molecular tubes for lipid sensingEnzymatic inhibitors, antibiotics, receptor analogs, and other biologically significant compounds (including total syntheses)

Technology Process of 4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane

There total 5 articles about 4,4,5,5-Tetramethyl-2-vinyl-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: 23.0%

ethene (74-85-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → ethylboronic acid pinacol ester (82954-89-0) + pinacol vinylboronate (75927-49-0)

Guidance literature:

RuH₂(H₂)2(tricyclohexylphosphine)2; In toluene;

DOI:10.1021/ja017429q

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) + vinylbis(diisopropylamino)borane (151293-63-9) → pinacol vinylboronate (75927-49-0)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; at 85 - 90 ℃; Reagent/catalyst; Inert atmosphere;

Reference yield:

C14H27B2O4(1-)*BrMg(1+) → 2,2',2''-(ethane-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (1361598-50-6) + pinacol vinylboronate (75927-49-0)

Guidance literature:

With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; tetrabutylammomium bromide; potassium iodide; In acetonitrile; at 20 ℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1002/anie.201903721

upstream raw materials:

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

vinylboronic acid

ethene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Downstream raw materials:

(3E,5E)-1,3,5-undecatriene

4,4,5,5-tetramethyl-2-[(E)-2-(4-nitrophenyl)ethenyl]-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-2-[(E)-2-p-tolylethenyl]-1,3,2-dioxaborolane

2-(4-fluorophenyl)-8-vinylimidazo[1,2-a]pyrazine