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). Boratflamme

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 Solder (; North American English, NA: ) is a fusible alloy, fusible metal alloy used to create a permanent bond between metal workpieces. Solder is melted in order to wet the parts of the joint, where it adheres to and connects the pieces aft ...

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:.{{OrgSynth, last1=Kidwell , first1=R. L. , last2=Murphy , first2=M. , last3=Darling , first3=S. D. , year=1969 , title=Phenols: 6-Methoxy-2-naphthol , volume=49 , pages=90 , collvol=10 , collvolpages=80 , prep=CV5P0918 : ArMgBr + B(OCH₃)₃ → MgBrOCH₃ + ArB(OCH₃)₂ :ArB(OCH₃)₂ + 2 H₂O → ArB(OH)₂ + 2 HOCH₃

References

External links

National Pollutant Inventory - Boron and compoundsMSDS for Trimethyl BorateWebBook page for BC₃H₉O₃
Methyl esters Borate esters Solvents