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374636

Sigma-Aldrich

Ethyl (S)-2-(trifluoromethylsulfonyloxy)propionate

≥96%

Synonym(s):

Ethyl O-trifluoromethanesulfonyl-L-lactate, Ethyl L-lactate 2-O-triflate

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About This Item

Linear Formula:
CH3CH(OSO2CF3)CO2C2H5
CAS Number:
84028-88-6
Molecular Weight:
250.19
Beilstein:
3549394
MDL number:
MFCD00134396
UNSPSC Code:
12352108
PubChem Substance ID:
24863321
NACRES:
NA.22

Assay

≥96%

optical activity

[α]20/D −44°, neat

contains

~1% MgO as stabilizer

refractive index

n20/D 1.374 (lit.)

bp

34 °C/0.005 mmHg (lit.)

density

1.342 g/mL at 25 °C (lit.)

functional group

ester
fluoro
triflate

storage temp.

−20°C

SMILES string

CCOC(=O)[C@H](C)OS(=O)(=O)C(F)(F)F

InChI

1S/C6H9F3O5S/c1-3-13-5(10)4(2)14-15(11,12)6(7,8)9/h4H,3H2,1-2H3/t4-/m0/s1

InChI key

RYSBPHXTNVWICH-BYPYZUCNSA-N

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Application

Ethyl (S)-2-(trifluoromethylsulfonyloxy)propionate can be used:
  • In the synthesis of tetra-methylated analog of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTMA) based chelates for imaging applications.
  • As a substrate in the synthesis of α-silylated carboxyl compounds via Cu-catalyzed stereoinvertive nucleophilic silylation of α-triflyloxy esters.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

174.2 °F - closed cup

Flash Point(C)

79 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBM0952V
BCBM0963V
1371350V
1381717
1371350

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Properties, solution state behavior, and crystal structures of chelates of DOTMA
Aime S, et al.
Inorganic Chemistry, 50(17), 7955-7965 (2011)
Copper-Catalyzed Substitution of α-Triflyloxy Nitriles and Esters with Silicon Nucleophiles under Inversion of the Configuration
Scharfbier J, et al.
Organic Letters, 19(24), 6562-6565 (2017)

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