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443999

Sigma-Aldrich

Trimethyl borate

purified by redistillation, ≥99.5%

Synonym(s):

Boric acid trimethyl ester, Methyl borate

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About This Item

Linear Formula:
B(OCH3)3
CAS Number:
Molecular Weight:
103.91
Beilstein:
1697939
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

vapor density

3.59 (vs air)

Assay

≥99.5%

form

liquid

purified by

redistillation

refractive index

n20/D 1.346 (lit.)

bp

68-69 °C (lit.)

mp

−34 °C (lit.)

density

0.932 g/mL at 20 °C (lit.)

SMILES string

COB(OC)OC

InChI

1S/C3H9BO3/c1-5-4(6-2)7-3/h1-3H3

InChI key

WRECIMRULFAWHA-UHFFFAOYSA-N

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Application

Trimethyl borate can be used as:
  • A reagent in the preparation of various trialkylamine−boranes from corresponding trialkylamines using lithium hydride/aluminum chloride catalyst.
  • A source of boron in the synthesis of boron nitride (BN) nanotubes by thermal-heating chemical vapor deposition (TH-CVD) method.
  • An electrolytic additive for electrochemical applications.
  • A reagent along with lithium di-tert-butyl(2,2,6,6-tetramethylpiperidino)zincate (TMP-zincate) for the synthesis of 1-tert-butyl-3,4-dihydroisoquinoline from isoquinoline via ortho metalation reaction.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Flam. Liq. 2 - Repr. 1B - STOT SE 1

Target Organs

Eyes

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

12.2 °F - (own results)

Flash Point(C)

-11 °C - (own results)

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Trimethyl borate-induced one-pot homologation reactions of isoquinoline with di-tert-butyl-TMP zincate
Seo HJ, et al.
Tetrahedron Letters, 52(29), 3747-3750 (2011)
Trimethyl borate as an electrolyte additive for high potential layered cathode with concurrent improvement of rate capability and cyclic stability
Wang Z, et al.
Electrochimica Acta, 184(1), 40-46 (2015)
Thermal-heating CVD synthesis of BN nanotubes from trimethyl borate and nitrogen gas.
Lin FH, et al.
Materials Chemistry and Physics, 107(1), 115-121 (2008)
One-Pot Synthesis of Ammonia-Borane and Trialkylamine-Boranes from Trimethyl Borate.
Veeraraghavan RP, et al.
Organic Letters, 14(24), 6119-6121 (2012)
Scott Gronert et al.
Journal of the American Society for Mass Spectrometry, 13(9), 1088-1098 (2002-09-27)
Using a quadrupole ion trap mass spectrometer, trimethyl borate was allowed to react with dihydrogen phosphate, deprotonated O-phosphoserine, and a set of hydrogen bonded complexes involving dihydrogen phosphate and neutral acids (phosphoric acid, acetic acid, serine, and O-phosphoserine). The reactions

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