Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

790184

Sigma-Aldrich

Sodium 1-(trifluoromethyl)cyclopropanesulfinate

Synonym(s):

Baran TFCS-Na Reagent

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C4H4F3NaO2S
Molecular Weight:
196.12
MDL number:
MFCD28124332
UNSPSC Code:
12352101
PubChem Substance ID:
329768203
NACRES:
NA.22

form

solid

Quality Level

100

reaction suitability

reaction type: C-C Bond Formation
reagent type: catalyst
reaction type: C-H Activation

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

Related Categories

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCB4125
MKBV7891V
MKBT1542V
MKBS4845V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Baran Diversinates™

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.

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