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452920

Sigma-Aldrich

Trimethyl borate

≥98%

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Synonym(s):
Boric acid trimethyl ester, Methyl borate
Linear Formula:
B(OCH3)3
CAS Number:
Molecular Weight:
103.91
Beilstein/REAXYS Number:
1697939
EC Number:
MDL number:
PubChem Substance ID:

vapor density

3.59 (vs air)

Quality Level

assay

≥98%

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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This Item
44399992330T59307
vibrant-m

452920

Trimethyl borate

vibrant-m

443999

Trimethyl borate

vibrant-m

92330

Trimethyl borate

vibrant-m

T59307

Triethyl borate

assay

≥98%

assay

≥99.5%

assay

≥99.0% (GC)

assay

99%

bp

68-69 °C (lit.)

bp

68-69 °C (lit.)

bp

68-69 °C (lit.)

bp

117-118 °C (lit.)

refractive index

n20/D 1.346 (lit.)

refractive index

n20/D 1.346 (lit.)

refractive index

n20/D 1.346 (lit.), n20/D 1.358

refractive index

n20/D 1.374 (lit.)

mp

−34 °C (lit.)

mp

−34 °C (lit.)

mp

−34 °C (lit.)

mp

-

density

0.932 g/mL at 20 °C (lit.)

density

0.932 g/mL at 20 °C (lit.)

density

0.932 g/mL at 20 °C (lit.)

density

0.858 g/mL at 25 °C (lit.)

Application

Trimethyl borate reacts with a Grignard reagent or organolithium compounds to yield dimethyl boronates, which upon subsequent aqueous acid treatment afford corresponding boronic acids. The resultant boronic acids or esters are useful intermediates in various cross-coupling reactions such as Suzuki coupling and Chan-Lam coupling. It is also used in the preparation of sodium borohydride.

Legal Information

ASCENSUS product

signalword

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

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

12.2 °F - (own results)

flash_point_c

-11 °C - (own results)

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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The Preparation of Sodium Borohydride by the High Temperature Reaction of Sodium Hydride with Borate Esters1.
Schlesinger H I, et al.
Journal of the American Chemical Society, 75(1), 205-209 (1953)
Cross?Coupling Reactions Of Organoboranes: An Easy Way To Construct C-C Bonds (Nobel Lecture)
Suzuki A
Angewandte Chemie (International Edition in English), 50(30), 6722-6737 (2011)
Boronic esters in stereodirected synthesis.
Matteson D S
Tetrahedron, 45(7), 1859-1885 (1989)
Palladium-catalyzed cross-coupling reactions of organoboron compounds.
Miyaura N and Suzuki A
Chemical Reviews, 95(7), 2457-2483 (1995)
New N-and O-arylations with phenylboronic acids and cupric acetate.
Chan D M, et al.
Tetrahedron Letters, 39(19), 2933-2936 (1998)

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