235113

Sigma-Aldrich

Trimethylsilyl bromoacetate

98%

Linear Formula:
BrCH2CO2Si(CH3)3
CAS Number:
Molecular Weight:
211.13
Beilstein/REAXYS Number:
1927560
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

vapor density

>1 (vs air)

assay

98%

refractive index

n20/D 1.442 (lit.)

bp

57-58 °C/9 mmHg (lit.)

density

1.284 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)OC(=O)CBr

InChI

1S/C5H11BrO2Si/c1-9(2,3)8-5(7)4-6/h4H2,1-3H3

InChI key

ZCHHFMWUDHXPFN-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

Trimethylsilyl bromoacetate has been used:
  • in the preparation of new imidazolium salts functionalized with the trimethylsilyl ester group
  • as alkylating agent in the synthesis of succinate fragment of pantocin B (antibiotic natural product)
  • in the synthesis of taxol derivatives tethered at C2′ and C-7 to glutamate and folate

Packaging

25 g in glass bottle

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2920 3(8) / PGII

WGK Germany

WGK 3

Flash Point(F)

116.6 °F - closed cup

Flash Point(C)

47 °C - closed cup

The [1, 2]-thio-Wittig rearrangement: evidence for a radical mechanism and its suppression.
Bertolli P, et al.
Tetrahedron Letters, 47(45), 7939-7942 (2006)
Jae Wook Lee et al.
Bioorganic & medicinal chemistry, 10(7), 2397-2414 (2002-05-02)
A series of Taxol derivatives tethered at C2' and C-7 to glutamate and folate have been synthesized for evaluation as prodrugs which release Taxol via hydrolytic lability of their alpha-alkoxy and alpha-amino esters. The half-time for hydrolysis of these materials...
Copper and palladium complexes with N-heterocyclic carbene ligands functionalised with carboxylate groups.
Danopoulos AA, et al.
Journal of Organometallic Chemistry, 693(21), 3369-3374 (2008)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.