Trimethylboroxine

Base Information

• Chemical Name: Trimethylboroxine
• CAS No.: 823-96-1
• Molecular Formula: C3H9B3O3
• Molecular Weight: 125.536
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID90341570
• Nikkaji Number: J375.125B
• Wikidata: Q15829729
• Mol file: 823-96-1.mol

Synonyms:Trimethylboroxine;823-96-1;Trimethylboroxin;2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane;2,4,6-Trimethylboroxin;Boroxin, trimethyl-;Trimethylboroxine 50% w/w soln. in THF;MFCD00013354;trimethyl-1,3,5,2,4,6-trioxatriborinane;2,4,6-Trimethyl-1,3,5,2,4,6-trioxatriborinane;2,4,6-Trimethylboroxine;Methaneboronic anhydride;trimethyboroxine;trimethyl boroxin;trimethylboroxaine;trimethyl boroxine;trimethyl-boroxine;Trimethylboroxine, 99%;2,4,6-trimethylboroxine;2,4,6-Trimethyl-boroxin;2,4,6-Trimethylboroxin #;SCHEMBL28307;C3H9B3O3;DTXSID90341570;2,4,6-trimethyl-cyclotriboroxane;AMY14910;BCP12493;AKOS015840980;AS-47572;FT-0632990;T3810;EN300-137197;F14364;Trimethylboroxine (ca. 50% in Tetrahydrofuran);Q-101084;Q15829729;Carbamicacid,[(1R)-1-(hydroxymethyl)-2-propynyl]-,1,1-dimethylethylester;2114129-19-8

Chemical Property of Trimethylboroxine

Chemical Property:

• Appearance/Colour: colorless to yellow solution
• Vapor Pressure: 100mmHg at 25°C
• Melting Point: -38 °C(lit.)
• Refractive Index: n20/D 1.362(lit.)
• Boiling Point: 79 °C at 760 mmHg
• Flash Point: 16°F
• PSA: 27.69000
• Density: 0.86 g/cm³
• LogP: 0.40380
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive & Hygroscopic
• Water Solubility.: Not miscible in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 126.0830846
• Heavy Atom Count: 9
• Complexity: 69.3

Purity/Quality:

99% ^*data from raw suppliers

Trimethylboroxin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C,Xi
• Hazard Codes: F,C,Xi
• Statements: 11-34-41-37/38-19
• Safety Statements: 9-16-26-33-36/37/39-45-46-37/39-3

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OB(OB(O1)C)C)C
• Uses: Trimethylboroxine is used as a derivatizing agent for GLC analysis. It is used in a diverse array of areas, including as a polymerization additive. It is also used in the preparation of CBS catalysts for asymmetric reductions. Trimethylboroxine (TMB) is a cyclic anhydride of methyl-boronic acid. It can be used as a:Methylating agent for the methylation of various aromatic halides and C(sp3)?H bonds using palladium catalyst.Reagent in the preparation of polymer supported CBS (Corey, Bakshi, and Shibata) catalysts. Trimethylboroxine (TMB) is a cyclic anhydride of methyl-boronic acid. It can be been used:As a derivatizing agent for gas chromatographic/mass spectrometric analysis.In the preparation of methylaluminoxane (MAO) which is used in the polymerization of olefins.As an electrolyte additive to enhance the interface stability of electrode/electrolyte.In methylation of aryl halides by palladium-catalyzed Suzuki-Miyaura coupling reaction.In the preparation of CBS (Corey, Bakshi and Shibata) catalysts for asymmetric reductions of ketones to alcohols.

Technology Process of Trimethylboroxine

There total 5 articles about Trimethylboroxine 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: 15.0%

dibromomethylborane (17933-16-3) + Hexamethyldisiloxane (107-46-0) + 1,1,1-trimethyl-N-phenyl-N-(trimethylsilyl)-silanamine (4147-89-1) → 5-phenyl-cyclo-1,3-dioxa-5-aza-2,4,6-trimethyl-2,4,6-triborane (81720-64-1) + Trimethylboroxine (823-96-1)

Guidance literature:

In dichloromethane; byproducts: C6H5NH2; under N2, to CH2Cl2 simultaneously added dropwise MeBBr2 (0.1 mole) and0.1 mole of mixt. of O(SiMe3)2 (0.066 mole) and PhN(SiMe3)2 (0.033 mole) at room temp., refluxed for 6 h; evapd., sepd. by distn.;

DOI:10.1016/0022-328X(85)80026-7

Reference yield:

Dimethylborinsaeure-anhydrid (19163-04-3) → trimethylborane (593-90-8) + Trimethylboroxine (823-96-1)

Guidance literature:

In not given; heating at high temp.; monitored by (11)B NMR;

DOI:10.1515/znb-2006-0804

Reference yield:

trimethylborane (593-90-8) + water (7732-18-5) → dihydroxy-methyl-borane (13061-96-6) + Trimethylboroxine (823-96-1) + Dimethylborinsaeure-anhydrid (19163-04-3)

Guidance literature:

at 320 ℃;

upstream raw materials:

trimethylborane

water

Dimethylborinsaeure-anhydrid

dibromomethylborane

Downstream raw materials:

triisobutylborane

(methyl)difluoroborane

1-methyl-1-vinylcyclohexane

n-propylidenecyclohexane

Refernces

• 1、 Wrackmeyer, Bernd,Tok, Oleg L.. "Indirect nuclear spin-spin coupling constants 1J( 17O,11B). First observation and calculation using density functional theory (DFT)". . p. 949 - 955. Retrieved 2008/09/16.