trimethyl borate
{{chembox
|Watchedfields = changed
|verifiedrevid = 470615177
|ImageFile_Ref = {{chemboximage|correct|??}}
|ImageFile = Structural formula of trimethyl borate.svg
|ImageSize = 200px
|ImageFile1 = Trimethyl-borate-3D-vdW.png
|IUPACName = Trimethyl borate
|OtherNames = Trimethoxyborane
|Section1 = {{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 8157
|InChI = 1/C3H9BO3/c1-5-4(6-2)7-3/h1-3H3
|InChIKey = WRECIMRULFAWHA-UHFFFAOYAY
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C3H9BO3/c1-5-4(6-2)7-3/h1-3H3
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = WRECIMRULFAWHA-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 121-43-7
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 82U64J6F5N
|PubChem = 8470
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 38913
|SMILES = O(B(OC)OC)C
|EINECS = 204-468-9
}}
|Section2 = {{Chembox Properties
|C = 3 | H = 9 | O = 3 | B = 1
|Appearance = colourless liquid
|Density = 0.932 g/ml
|MeltingPtC = −34
|BoilingPtC = 68 to 69
|Solubility = decomposition
}}
|Section3 = {{Chembox Hazards
|MainHazards = flammable
}}
|Section4 = {{Chembox Related
|OtherCations = Trimethyl phosphite
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.{{Ullmann|author=Robert J. Brotherton |author2=C. Joseph Weber |author3=Clarence R. Guibert |author4=John L. Little |title=Boron Compounds|year=2000|doi-10.1002/14356007.a04_309}} 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).{{cite journal |journal=Polymer |date=September 1996 |volume=37 |issue=20 |pages=4629-4631 |last1=Beckett |first1=M. A. |last2=Strickland |first2=G. C. |last3=Holland |first3=J. R. |last4=Varma |first4=K. S. |title=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 |doi=10.1016/0032-3861(96)00323-0 }}
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:.{{OrgSynth|last1=Ishihara |first1=Kazuaki |last2=Ohara |first2=Suguru |last3=Yamamoto |first3=Hisashi |year=2002 |title=3,4,5-Trifluorophenylboronic Acid |volume=79 |pages=176 |collvol=10 |collvolpages=80 |prep=V79P0176}}{{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
- [https://web.archive.org/web/20060209040519/http://www.npi.gov.au/database/substance-info/profiles/15.html National Pollutant Inventory - Boron and compounds]
- [https://archive.today/20130204204224/http://www.trimethylborate.com/wcm/products/product_detail.page?display-mode=msds&product=1120456&application=1120208 MSDS for Trimethyl Borate]
- [http://webbook.nist.gov/cgi/cbook.cgi?ID=C121437 WebBook page for BC3H9O3]