823-96-1

Basic information

• Product Name: Trimethylboroxine
• Synonyms: Trimethylboroxin, in tetrahydrofuran;Trimethylboroxine, 50 wt% solution in THF;2,4,6-Trimethyl-cyclotriboroxane;Boroxin, 2,4,6-trimethyl-;2,4,6-Trimethyl-1,3,5-trioxa-2,4,6-triboracyclohexane;2,4,6-Trimethylboroxin;Methaneboronic anhydride;Methylboric anhydride
• CAS NO: 823-96-1
• Molecular Formula: C₃H₉B₃O₃
• Molecular Weight: 125.53
• Product Categories: API intermediates;Boronic Acids and Derivatives;Organometallic Reagents;Others
• Mol File: 823-96-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: −38 °C(lit.)
• Boiling Point: 78-80 °C(lit.)
• Flash Point: 16 °F
• Appearance: Colorless to yellow/Solution
• Density: 0.898 g/mL at 25 °C(lit.)
• Vapor Pressure: 100mmHg at 25°C
• Refractive Index: n20/D 1.362(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Not miscible in water.
• Sensitive: Moisture Sensitive & Hygroscopic
• BRN: 1757008
• CAS DataBase Reference: Trimethylboroxine(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethylboroxine(823-96-1)
• EPA Substance Registry System: Trimethylboroxine(823-96-1)

Safety Data

• 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
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 3
• F: 2-10-21
• TSCA: Yes
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 823-96-1(Hazardous Substances Data)

Usage

Chemical Properties

colorless to yellow solution

Uses

Different sources of media describe the Uses of 823-96-1 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.

Application

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.

Purification Methods

Possible impurity is methylboronic acid. If present, then add a few drops of conc H2SO4 and distil it immediately, then fractionate it through an efficient column. [McCusker et al. J Am Chem Soc 79 5179 1957, IR: Goubeau & Keller Z Anorg Allgem Chem 272 303 1953, Beilstein 4 IV 4378.]

InChI:InChI=1/C3H9B3O3/c1-4-7-5(2)9-6(3)8-4/h1-3H3

Upstream product

• 201230-82-2 carbon monoxide 
• 944069-56-1 ((C₂H₅)3NBH₂)2H⁽¹⁺⁾*B(C₆F₅)4^(1-)=(((C₂H₅)3NBH₂)2H)B(C₆F₅)4 
• 17933-16-3 dibromomethylborane 
• 107-46-0 Hexamethyldisiloxane 
• 4147-89-1 1,1,1-trimethyl-N-phenyl-N-(trimethylsilyl)-silanamine 
• 19163-04-3 Dimethylborinsaeure-anhydrid 
• 593-90-8 trimethylborane 
• 7732-18-5 water 

Downstream Products

• 1009334-37-5 3-(2-fluoro-4-trimethylsilanylphenylamino)-7-methylfuro[3,2-c]pyridine-2-carboxylic acid ethyl ester 
• 1009334-77-3 3-(2-fluoro-4-trimethylsilanyl-phenylamino)-4-methyl-furo[3,2-c]pyridine-2-carboxylic acid ethyl ester 
• 939812-63-2 tert-butyl {(1S,2S)-2-[(5-chloro-2-cyano-4-methylphenyl)amino]cyclohexyl}carbamate 
• 849546-52-7 4-(3-fluorophenyl)-6-methoxy-1-methylisoquinoline-3-carbonitrile 
• 26286-51-1 2-methyl-1-(2-nitrophenyl)-1H-imidazole 
• 7318-81-2 bis(methoxy)methylborane 
• 107-31-3 Methyl formate 
• 1065114-20-6 2,7-dibenzyl-4-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine 
• 121-43-7 Trimethyl borate 
• 4887-24-5 triacetoxyborane 
• 688-71-1 tri-n-propyl borate 
• 17933-10-7 ethyl-dibromo-borane 
• 13703-95-2 fluoroboroxine 
• 373-64-8 (methyl)difluoroborane 

Relevant articles and documents

Complete reductive cleavage of CO facilitated by highly electrophilic borocations

The addition of CO to [((R3N)BH2)2(μ-H)][B(C6F5)4] leads to formation of trimethylboroxine ((MeBO)3) and [(R3N)2BH2][B(C6F5

GEZIELTE SYNTHESEN FUER BOROXAZINE

Cyclo-1-oxa-3,5-diaza-2,4,6-triboranes (A) and cyclo-1,3-dioxa-5-aza-2,4,6-triboranes (B) have been prepared by four different methods: (1) from mixtures of hexamethyldisilazanes and hexamethyldisiloxane with CH3BBr2 (A and B); (2) from (CH3)3SiN2 and CH3BBr2 (B); (3) from cyclo-1-oxa-3,5-diaza-2,4,6-trisilanes and CH3BBr2 (A); and (4) from CH3B2 and hexamethyldisiloxane (A).The products and some by-products were characterized by mass and NMR (1H, 11B, 29Si) spectra.Substances which were separated from the by-products were also analysed.