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Trimethyl borate
Chemical compound

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. It is a weak Lewis acid (AN = 23, Gutmann-Beckett method).

Borate esters are prepared by heating boric acid or related boron oxides with alcohols under conditions where water is removed by azeotropic distillation.

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Applications

Trimethyl borate is the main precursor to sodium borohydride by its reaction with sodium hydride in the Brown-Schlesinger process:

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.4

Organic synthesis

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:.56

ArMgBr + B(OCH3)3 → MgBrOCH3 + ArB(OCH3)2 ArB(OCH3)2 + 2 H2O → ArB(OH)2 + 2 HOCH3

References

  1. Robert J. Brotherton; C. Joseph Weber; Clarence R. Guibert; John L. Little (2000). "Boron Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3-527-30673-2. 978-3-527-30673-2 ↩

  2. Beckett, M. A.; Strickland, G. C.; Holland, J. R.; Varma, K. S. (September 1996). "A convenient n.m.r. method for the measurement of Lewis acidity at boron centres: correlation of reaction rates of Lewis acid initiated epoxide polymerizations with Lewis acidity". Polymer. 37 (20): 4629–4631. doi:10.1016/0032-3861(96)00323-0. /wiki/Doi_(identifier) ↩

  3. Robert J. Brotherton; C. Joseph Weber; Clarence R. Guibert; John L. Little (2000). "Boron Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3-527-30673-2. 978-3-527-30673-2 ↩

  4. Robert J. Brotherton; C. Joseph Weber; Clarence R. Guibert; John L. Little (2000). "Boron Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3-527-30673-2. 978-3-527-30673-2 ↩

  5. Ishihara, Kazuaki; Ohara, Suguru; Yamamoto, Hisashi (2002). "3,4,5-Trifluorophenylboronic Acid". Organic Syntheses. 79: 176; Collected Volumes, vol. 10, p. 80. http://www.orgsyn.org/demo.aspx?prep=V79P0176 ↩

  6. Kidwell, R. L.; Murphy, M.; Darling, S. D. (1969). "Phenols: 6-Methoxy-2-naphthol". Organic Syntheses. 49: 90; Collected Volumes, vol. 10, p. 80. http://www.orgsyn.org/demo.aspx?prep=CV5P0918 ↩