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Trimethyl borate

Chemical compound From Wikipedia, the free encyclopedia

Trimethyl borate

Trimethyl borate is the organoboron compound with the formula B(OCH3)3. It is a colourless liquid that burns with a green flame.[1] 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).[2]

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This chemical is quite flammable and burns with a green flame
Quick Facts Names, Identifiers ...
Trimethyl borate
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Names
IUPAC name
Trimethyl borate
Other names
Trimethoxyborane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.063
EC Number
  • 204-468-9
UNII
  • InChI=1S/C3H9BO3/c1-5-4(6-2)7-3/h1-3H3 Y
    Key: WRECIMRULFAWHA-UHFFFAOYSA-N Y
  • InChI=1/C3H9BO3/c1-5-4(6-2)7-3/h1-3H3
    Key: WRECIMRULFAWHA-UHFFFAOYAY
  • O(B(OC)OC)C
Properties
C3H9BO3
Molar mass 103.91 g·mol−1
Appearance colourless liquid
Density 0.932 g/ml
Melting point −34 °C (−29 °F; 239 K)
Boiling point 68 to 69 °C (154 to 156 °F; 341 to 342 K)
decomposition
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 flammable
Related compounds
Other cations
 Trimethyl phosphite
Tetramethyl orthosilicate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Borate esters are prepared by heating boric acid or related boron oxides with alcohols under conditions where water is removed by azeotropic distillation. [1]

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.[1]

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:.[3][4]

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

References

External links

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