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

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane
• CAS No.: 25015-63-8
• Molecular Formula: C6H13BO2
• Molecular Weight: 127.979
• Hs Code.: 29209090
• European Community (EC) Number: 607-485-3
• DSSTox Substance ID: DTXSID30422852
• Nikkaji Number: J2.868.080E
• Wikipedia: Pinacolborane
• Wikidata: Q72499869
• Mol file: 25015-63-8.mol

Synonyms:4,4,5,5-tetramethyl(1,3,2)dioxaborolane;pinacolborane

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

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 28.6mmHg at 25°C
• Refractive Index: n20/D 1.396(lit.)
• Boiling Point: 109.9 °C at 760 mmHg
• Flash Point: 20.2 °C
• PSA: 18.46000
• Density: 0.882 g/cm³
• LogP: 0.85690
• Storage Temp.: Keep Cold
• Sensitive.: Air Sensitive
• Solubility.: Miscible with ether, dichloromethane, tetrahydrofuran and organi
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 127.0930348
• Heavy Atom Count: 9
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

Pinacolborane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi,Xn
• Statements: 11-15-36/37/38-36/37-19-40
• Safety Statements: 16-43-8-37/39-26-33-29-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [B]1OC(C(O1)(C)C)(C)C
• Uses: Pinacolborane is used for synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence. Pinacolborane is used as a precursor of boronic esters by hydroboration or coupling reactions. It acts as a monofunctional hydroborating agent. It is used in the synthesis of unsymmetrical biaryls through aromatic C-H borylation-cross-coupling sequence. It is involved in the preparation of 4,4,5,5-tetramethyl-2-thiophen-2-yl-[1,3,2]dioxaborolane by reacting with 2-iodo-thiophene. Further, it is used to prepare vinylboronates by palladium-catalyzed coupling with alkenyl triflates and iodides.

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

There total 55 articles about 4,4,5,5-Tetramethyl-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: 95.0%

(pentamethylcyclopentadienyl)Rh(H)(pinacolboryl)3 + benzene-d6 (1076-43-3) → deutero-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (680192-98-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + 4,4,5,5-tetramethyl-2-d5-phenyl[1,3,2]dioxaborolane

Guidance literature:

In benzene-d6; (N2); heated at 55°C for 90 min; not isolated, detected by NMR;

DOI:10.1021/ja045090c

Reference yield: 91.0%

Ethyl tert-butyl ether (637-92-3) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + 2-(2-tert-butoxyethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (255041-56-6)

Guidance literature:

(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I); In neat (no solvent); for 24 h at 150°C;

DOI:10.1021/ja044933x

Reference yield: 91.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + dichloroborane (10325-39-0) → 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8)

Guidance literature:

With triethylamine; In 1,4-dioxane; at 0 - 20 ℃; for 12h; pH=12; Solvent; pH-value; Reagent/catalyst; Concentration; Inert atmosphere;

upstream raw materials:

methylbutane

bis(pinacol)diborane

Ethyl tert-butyl ether

dibutyl ether

Downstream raw materials:

2-thiopheneboronic acid pinacol ester

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

methoxybenzene

2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Refernces

• 1、 Braunschweig, Holger,Guethlein, Frank,Mailaender, Lisa,Marder, Todd B.. "Synthesis of catechol-, pinacol-, and neopentylglycolborane through the heterogeneous catalytic B-B hydrogenolysis of diboranes(4)". . p. 14831 - 14835. Retrieved 2013.
• 2、 Benn, Kieran,Nicholson, Kieran,Langer, Thomas,Thomas, Stephen P.. "A boron-nitrogen transborylation enabled, borane-catalysed reductive cyanation of enones". supporting information. p. 9406 - 9409. Retrieved 2021/09/22.
• 3、 Lee, Hyune-Jea,Yonekura, Yuya,Kim, Nayoung,Yoshida, Jun-Ichi,Kim, Heejin. "Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis- trans Isomerization in Flow". supporting information. p. 2904 - 2910. Retrieved 2021/05/05.