790184

Sigma-Aldrich

Sodium 1-(trifluoromethyl)cyclopropanesulfinate

Synonym(s):
Baran TFCS-Na Reagent
Empirical Formula (Hill Notation):
C4H4F3NaO2S
Molecular Weight:
196.12
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

reaction suitability

reagent type: catalyst
reaction type: C-H Activation

Quality Level

mp

287-292 °C

SMILES string

[O-]S(C1(CC1)C(F)(F)F)=O.[Na+]

InChI

1S/C4H5F3O2S.Na/c5-4(6,7)3(1-2-3)10(8)9;/h1-2H2,(H,8,9);/q;+1/p-1

InChI key

IZLDENBRBYPDNY-UHFFFAOYSA-M

Application

TFCS-Na is a diversification reagent for the C-H Functionalization of several classes of heterocycles. This reagent installs the trifluoromethylcyclopropyl group, which was recently reported to increase metabolic stability compared to compounds containing the tert-butyl group.

Simple Sulfinate Synthesis Enables C-H Trifluoromethylcyclopropanation

Packaging

5 g in glass bottle
500 mg in amber glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26-36/39

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
David Barnes-Seeman et al.
ACS medicinal chemistry letters, 4(6), 514-516 (2014-06-06)
Susceptibility to metabolism is a common issue with the tert-butyl group on compounds of medicinal interest. We demonstrate an approach of removing all the fully sp(3) C-Hs from a tert-butyl group: replacing some C-Hs with C-Fs and increasing the s-character...
Articles
The synthesis of heteroaromatic and aromatic compounds is at the heart of the chemical industry. The ever-growing demand for new chemical entities, coupled with dwindling resources and time constraints allotted to any given research project, a rapid way to diversify (hetero)aromatic scaffolds is needed.
Read More

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