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

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane 97% ^*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
• General Description: Pinacolborane (HBpin) is a versatile hydroboration reagent that effectively reacts with imines in the presence of the catalyst tris[3,5-bis(trifluoromethyl)phenyl]borane (BArF₃), enabling metal-free imine hydroboration at room temperature without requiring an additional Lewis base. Its reactivity is attributed to the ability of BArF₃ to coordinate with the imine nitrogen, facilitating hydride transfer from HBpin. This highlights HBpin's utility in amine synthesis and underscores the role of steric effects in catalytic efficiency.

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

4-chlorophenylboronic acid pinacol ester

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene

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

Refernces

BAr^F₃-Catalyzed Imine Hydroboration with Pinacolborane Not Requiring the Assistance of an Additional Lewis Base

10.1021/acs.organomet.7b00381

The research explores the use of tris[3,5-bis(trifluoromethyl)phenyl]borane (BArF3) as a highly effective catalyst for the metal-free hydroboration of imines, a process that is crucial for the preparation of amines. The study demonstrates that BArF3 outperforms other Lewis acidic boranes, such as the commonly used tris(pentafluorophenyl)borane (B(C6F5)3), in facilitating the reaction of ketimines and aldimines with pinacolborane (HBpin) at room temperature without the need for an additional Lewis base. The researchers concluded that the steric hindrance caused by the six ortho fluorine atoms in B(C6F5)3 accounts for its lower reactivity compared to BArF3. The study provides a new protocol for imine hydroboration that does not require external Lewis bases and offers insights into the mechanism of the reaction, suggesting that BArF3 coordinates with the imine nitrogen atom, activating it for hydride transfer from HBpin. The work highlights the importance of steric effects in catalysis and contributes to the understanding of boron Lewis acid catalysis in organic synthesis.