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Trimethyl borate

Trimethyl borate

Tetramethyl orthosilicate

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).

This chemical is quite flammable and burns with a green flame

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

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.

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

References

References

  1. Robert J. Brotherton. (2000). "Boron Compounds".
  2. (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.
  3. (2002). "3,4,5-Trifluorophenylboronic Acid".
  4. (1969). "Phenols: 6-Methoxy-2-naphthol".
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methyl-esters borate-esters ester-solvents
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