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235113

Sigma-Aldrich

Trimethylsilyl bromoacetate

98%

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Linear Formula:
BrCH2CO2Si(CH3)3
CAS Number:
Molecular Weight:
211.13
Beilstein:
1927560
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

>1 (vs air)

Quality Level

Assay

98%

form

liquid

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

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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

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

116.6 °F

Flash Point(C)

47 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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)
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
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)

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