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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

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Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-5.8 °F

flash_point_c

-21 °C

Certificates of Analysis (COA)

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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
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)
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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