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Merck
CN

452920

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
EC Number:
204-468-9
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24868738
Beilstein/REAXYS Number:
1697939
MDL number:
MFCD00008346

Key Documents

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Product Name

Trimethyl borate, ≥98%

InChI key

WRECIMRULFAWHA-UHFFFAOYSA-N

InChI

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

SMILES string

COB(OC)OC

vapor density

3.59 (vs air)

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.)

Quality Level

200

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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

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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

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBT2670
SHBS8105
SHBS4897
SHBR1475
SHBP0957

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New N-and O-arylations with phenylboronic acids and cupric acetate.
Chan D M, et al.
Tetrahedron Letters, 39(19), 2933-2936 (1998)
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)
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