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903965

Sigma-Aldrich

Trimethylboroxine

50% THF solution

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
MDL number:
MFCD00013354
UNSPSC Code:
12352103
NACRES:
NA.22

form

liquid

refractive index

n/D 1.3880

density

0.89962 g/mL

InChI

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

InChI key

GBBSAMQTQCPOBF-UHFFFAOYSA-N

Application

Trimethylboroxine (TMB) is a cyclic anhydride of methyl-boronic acid. It can be used as a:
  • Methylating agent for the methylation of various aromatic halides and C(sp3)−H bonds using palladium catalyst.
  • Reagent in the preparation of polymer supported CBS (Corey, Bakshi, and Shibata) catalysts.

Other Notes

Organoboranes. 39. Convenient procedures for the preparation of methylboronic acid and trimethylboroxin

related product

Product No.
Description
Pricing

Signal Word

Danger

Hazard Statements

H225,H314,H335,H351

Hazard Classifications

Carc. 2 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-5.8 °F

Flash Point(C)

-21 °C

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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Profound Methyl Effects in Drug Discovery and a Call for New C−H Methylation Reactions.
Schoenherr H and Cernak T
Angewandte Chemie (International ed. in English), 52(47), 12256-12267 (2013)
Oxazaborolidines as functional monomers: ketone reduction using polymer-supported Corey, Bakshi, and Shibata catalysts.
Price MD, et al.
The Journal of Organic Chemistry, 67(23), 8086-8089 (2002)
Jacob B Geri et al.
Journal of the American Chemical Society, 139(29), 9811-9814 (2017-07-14)
We present a strategy to rationally prepare CF3- transfer reagents at ambient temperature from HCF3. We demonstrate that a highly reactive CF3- adduct can be synthesized from alkali metal hydride, HCF3, and borazine Lewis acids in quantitative yield at room
Practical methylation of aryl halides by Suzuki-Miyaura coupling.
Gray M, et al.
Tetrahedron Letters, 41(32), 6237-6240 (2000)
Anne Rietz et al.
Journal of medicinal chemistry, 60(11), 4594-4610 (2017-05-10)
Spinal muscular atrophy (SMA) is the leading genetic cause of infant death. We previously developed a high-throughput assay that employs an SMN2-luciferase reporter allowing identification of compounds that act transcriptionally, enhance exon recognition, or stabilize the SMN protein. We describe

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