trimethoxyborane, boron trimethoxide
|Molar mass||103.91 g·mol−1|
|Melting point||−34 °C (−29 °F; 239 K)|
|Boiling point||68 °C (154 °F; 341 K)|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
Trimethyl borate is the organoboron compound with the formula B(OCH3)3. It is a colourless liquid that burns with a green flame. It is an intermediate in the preparation of sodium borohydride and is a popular reagent in organic chemistry.
- 4 NaH + B(OCH3)3 → NaBH4 + 3 NaOCH3
It is a gaseous anti-oxidant in brazing and solder flux. Otherwise, trimethyl borate has no announced commercial applications. It has been explored as a fire retardant, as well as being examined as an additive to some polymers. It is a useful reagent in organic synthesis, as a precursor to boronic acids, which are used in Suzuki couplings. These boronic acids are prepared via reaction of the trimethyl borate with Grignard reagents followed by hydrolysis:.
- ArMgBr + B(OCH3)3 → MgBrOCH3 + ArB(OCH3)2
- ArB(OCH3)2 + 2 H2O → ArB(OH)2 + 2 HOCH3
- Robert J. Brotherton, C. Joseph Weber, Clarence R. Guibert, John L. Little "Boron Compounds" in Ullmann's Encyclopedia of Industrial Chemistry 2000, Wiley-VCH. doi:10.1002/14356007.a04_309
- Kazuaki Ishihara, Suguru Ohara, Hisashi Yamamoto (2002). "3,4,5-Trifluorophenylboronic Acid". Org. Synth. 79: 176.; Coll. Vol. 10, p. 80
- R. L. Kidwell, M. Murphy, and S. D. Darling (1969). "Phenols: 6-Methoxy-2-naphthol". Org. Synth. 49: 90.; Coll. Vol. 10, p. 80