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Merck

452920

Sigma-Aldrich

Trimethyl borate

≥98%

Synonym(s):

Boric acid trimethyl ester, Methyl borate

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100 ML
MXP 2,831.00
1 L
MXP 3,934.00
2 L
MXP 5,391.00

MXP 2,831.00


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Estimated to ship on09 March 2025


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100 ML
MXP 2,831.00
1 L
MXP 3,934.00
2 L
MXP 5,391.00

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

MXP 2,831.00


Availability

Estimated to ship on09 March 2025


To order products, please contact your local dealer.

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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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.[1] The resultant boronic acids or esters are useful intermediates in various cross-coupling reactions such as Suzuki coupling[2][3] and Chan-Lam coupling.[4] It is also used in the preparation of sodium borohydride.[5]

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

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

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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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