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452920

Sigma-Aldrich

Trimethyl borate

≥98%

Synonym(s):

Boric acid trimethyl ester, Methyl borate

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About This Item

Linear Formula:
B(OCH3)3
CAS Number:
121-43-7
Molecular Weight:
103.91
Beilstein:
1697939
EC Number:
204-468-9
MDL number:
MFCD00008346
UNSPSC Code:
12352103
PubChem Substance ID:
24868738
NACRES:
NA.22

vapor density

3.59 (vs air)

Quality Level

200

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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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

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

WGK

WGK 1

Flash Point(F)

12.2 °F

Flash Point(C)

-11 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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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