- Trimethylboroxine
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2025-06-20
- CAS:823-96-1
- Min. Order: 1kg
- Purity: 0.99
- Supply Ability: 10 tons
- Trimethylboroxine
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- $6.00
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2025-05-26
- CAS:823-96-1
- Min. Order: 1kg
- Purity: 0.99
- Supply Ability: 100000
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| | Trimethylboroxine Basic information |
| Product Name: | Trimethylboroxine | | Synonyms: | 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;Trimethylboroxine, 3.5M (50 wt.%) solution in THF;Trimethylboroxine, 3.5M (50 wt.%) solution in THF, AcroSeal | | CAS: | 823-96-1 | | MF: | C3H9B3O3 | | MW: | 125.53 | | EINECS: | | | Product Categories: | API intermediates;Boronic Acids and Derivatives;Organometallic Reagents;Others | | Mol File: | 823-96-1.mol |  |
| | Trimethylboroxine Chemical Properties |
| Melting point | −38 °C(lit.) | | Boiling point | 78-80 °C(lit.) | | density | 0.898 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.362(lit.) | | Fp | 16 °F | | storage temp. | Flammables area | | solubility | Chloroform (Sparingly), Dichloromethane (Slightly), THF (Soluble) | | form | Solution | | color | Colorless to yellow | | Water Solubility | Not miscible in water. | | Sensitive | Moisture Sensitive & Hygroscopic | | BRN | 1757008 | | InChI | 1S/C3H9B3O3/c1-4-7-5(2)9-6(3)8-4/h1-3H3 | | InChIKey | GBBSAMQTQCPOBF-UHFFFAOYSA-N | | SMILES | Cb1ob(C)ob(C)o1 | | CAS DataBase Reference | 823-96-1(CAS DataBase Reference) |
| | Trimethylboroxine Usage And Synthesis |
| Chemical Properties | colorless to yellow solution | | Uses | 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.
| | 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. | | Uses | 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.
| | Preparation |
Trimethylboroxine is prepared by heating B(CH3)3 and B2O3 together in a sealed tube. The B2O3 powder is made by dehydrating H3BO3 under vacuum over P2O5 , at 220℃. The very hygro-scopic oxide is placed with strict exclusion of moisture in a 200-ml. thick-wall Pyrex tube provided with a ground joint, and a melting-point capillary is fastened to the tube just below the joint. The tube is connected to a vacuum pump and immersed in liquid nitrogen, and when a high vacuum has been established, a quantity of B(CH3)3 equivalent to 4.25 g. (0.061 mole) of B2O3 is condensed in the tube. The tube is sealed off, heated to 600℃ and kept at this temperature for six hours; in the process the contents turn into a clear, colorless liquid. When the tube has cooled down, the tip is broken under a nitrogen blanket and sealed to a tube leading to the vacuum pump. The tube is evacuated and the contents of the tube are transferred into a -78℃ trap. The crude product is purified by removing volatile contaminants at -45℃ and then distilling the product from a -10℃ trap into a receiver held at -78℃.
| | 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.] | | Structure and conformation | The B and O atoms in trimethylboroxine form a symmetrical six-membered ring.
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| | Trimethylboroxine Preparation Products And Raw materials |
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