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

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

Uses

Used in Analytical Chemistry:
Trimethylboroxine is used as a derivatizing agent for gas chromatographic (GLC) analysis. It helps in the identification and quantification of various organic compounds by converting them into more volatile and thermally stable derivatives.
Used in Polymer Industry:
Trimethylboroxine is used as a polymerization additive. It enhances the properties of polymers, such as their stability, processability, and performance, making them suitable for various applications.
Used in Catalyst Preparation:
Trimethylboroxine is used in the preparation of CBS (Corey, Bakshi, and Shibata) catalysts for asymmetric reductions. These catalysts are essential in the synthesis of enantiomerically pure compounds, which are crucial in pharmaceutical and agrochemical industries.
Used in Organic Synthesis:
Trimethylboroxine serves as a methylating agent for the methylation of various aromatic halides and C(sp3)-H bonds using palladium catalysts. This reaction is widely used in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Olefin Polymerization:
Trimethylboroxine is used in the preparation of methylaluminoxane (MAO), which is an essential component in the polymerization of olefins. This process leads to the production of high-quality polymers with improved properties.
Used in Electrochemistry:
Trimethylboroxine acts as an electrolyte additive to enhance the interface stability of electrode/electrolyte systems. This improves the performance and longevity of batteries and fuel cells.
Used in Suzuki-Miyaura Coupling Reaction:
Trimethylboroxine is employed in the methylation of aryl halides by palladium-catalyzed Suzuki-Miyaura coupling reaction. This reaction is a crucial method for the formation of carbon-carbon bonds in organic synthesis, particularly in the production of biologically active compounds and advanced materials.

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

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

Downstream Products

• 1116-39-8 triisobutylborane 
• 373-64-8 (methyl)difluoroborane 
• 21623-78-9 1-methyl-1-vinylcyclohexane 
• 2129-93-3 n-propylidenecyclohexane 
• 18699-87-1 2-methyl-3-nitropyridine 
• 5028-23-9 N,N-dimethyl-3-nitropyridin-2-amine 
• 90-12-0 1-Methylnaphthalene 
• 134-84-9 4-Methylbenzophenone 
• 104-85-8 para-methylbenzonitrile 
• 89976-12-5 1-methyl-4-nitro-2-(trifluoromethyl) benzene 
• 261945-82-8 1,5-dimethyl-2-nitro-4-(trifluoromethyl)benzene 
• 122-00-9 para-methylacetophenone 
• 112022-83-0 (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole 
• 112022-81-8 (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole 

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

Indirect nuclear spin-spin coupling constants 1J( 17O,11B). First observation and calculation using density functional theory (DFT)

Coupling constants 1J(17O,11B) of borates, borane adducts and boranes with boron-oxygen bonds have been calculated on the basis of optimised molecular structures using the B3LYP/6-311+G(d,p) level of theory. This indicates that such coupling constants can be of either sign and that their magnitudes can be rather small. Since both 11B and 17O are quadrupole nuclei, it is therefore difficult to measure representative data. In the cases of trimethoxyborane and tetraethyldiboroxanes, it proved possible to obtain experimental data 1J( 17O,11B) (22 and 18 Hz) by measurement of 17O NMR spectra at high temperature (120 °C and 160 °C) respectively. The magnitude of these coupling constants is in reasonable agreement with calculated data. In the case of the diboroxane, this points towards a bond angle B-O-B more close to 180° than to 140°.

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.