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Merck

323136

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:
823-96-1
Molecular Weight:
125.53
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24859217
MDL number:
MFCD00013354
Beilstein/REAXYS Number:
1757008

Key Documents

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InChI

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

SMILES string

Cb1ob(C)ob(C)o1

InChI key

GBBSAMQTQCPOBF-UHFFFAOYSA-N

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.)

Quality Level

100

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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.

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

hcodes

H225,H314

Hazard Classifications

Flam. Liq. 2 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

15.8 °F - closed cup

flash_point_c

-9 °C - closed cup

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Class I Designated Chemical Substances

prtr

Group 4: Flammable liquids + Type 1 petroleums + Hazardous rank II + Water insoluble liquid

fsl

323136-250G: + 323136-VAR: + 323136-BULK: + 323136-25G: + 323136-1G: + 323136-5G:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM7888
SHBL8912
SHBL5639
SHBK1263
SHBK1262

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Tetrahedron Asymmetry, 14, 2115-2118 (2003)
Reactivity of metallocene catalysts for olefin polymerization: influence of activator nature and structure
Pedeutour JN
Macromolecular Rapid Communications, 22(14), 1095-1123 (2001)
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)
Zoltán Dalicsek et al.
Organic letters, 7(15), 3243-3246 (2005-07-16)
[reaction: see text]. An operationally simple and recoverable fluorous CBS methodology was developed. The in situ-generated fluorous oxazaborolidine efficiently catalyzed the reduction of ketones with high enantioselectivity and reactivity. The subsequent recycling of the fluorous prolinol precatalyst was achieved by
Practical methylation of aryl halides by Suzuki-Miyaura coupling.
Gray M, et al.
Tetrahedron Letters, 41(32), 6237-6240 (2000)
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