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323136

Sigma-Aldrich

Trimethylboroxine

99%

Synonym(s):

2,4,6-Trimethyl-1,3,5,2,4,6-trioxatriborinane, 2,4,6-Trimethylboroxine, Methaneboronic anhydride, Trimethyl-1,3,5,2,4,6-trioxatriborinane

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About This Item

Empirical Formula (Hill Notation):
C3H9B3O3
CAS Number:
Molecular Weight:
125.53
Beilstein:
1757008
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

liquid

refractive index

n20/D 1.362 (lit.)

bp

78-80 °C (lit.)

mp

−38 °C (lit.)

density

0.898 g/mL at 25 °C (lit.)

SMILES string

Cb1ob(C)ob(C)o1

InChI

1S/C3H9B3O3/c1-4-7-5(2)9-6(3)8-4/h1-3H3

InChI key

GBBSAMQTQCPOBF-UHFFFAOYSA-N

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Application

Trimethylboroxine (TMB) is a cyclic anhydride of methyl-boronic acid. It can be been used:
  • As a derivatizing agent for gas chromatographic/mass spectrometric analysis.
  • In the preparation of methylaluminoxane (MAO) which is used in the polymerization of olefins.
  • As an electrolyte additive to enhance the interface stability of electrode/electrolyte.
  • In methylation of aryl halides by palladium-catalyzed Suzuki-Miyaura coupling reaction.
  • In the preparation of CBS (Corey, Bakshi and Shibata) catalysts for asymmetric reductions of ketones to alcohols.

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Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Flam. Liq. 2 - Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

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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Enhanced high voltage performances of layered lithium nickel cobalt manganese oxide cathode by using trimethylboroxine as electrolyte additive
Yu Q, et al.
Electrochimica Acta, 176(14), 919-925 (2015)
Polymer, 37, 4629-4629 (1996)
Reactivity of metallocene catalysts for olefin polymerization: influence of activator nature and structure
Pedeutour JN
Macromolecular Rapid Communications, 22(14), 1095-1123 (2001)
Tetrahedron Asymmetry, 14, 2115-2118 (2003)
Practical methylation of aryl halides by Suzuki-Miyaura coupling.
Gray M, et al.
Tetrahedron Letters, 41(32), 6237-6240 (2000)

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