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Merck
CN

790184

Sodium 1-(trifluoromethyl)cyclopropanesulfinate

Synonym(s):

Baran TFCS-Na Reagent

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About This Item

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

Key Documents

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InChI

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

SMILES string

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

InChI key

IZLDENBRBYPDNY-UHFFFAOYSA-M

form

solid

reaction suitability

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

mp

287-292 °C

functional group

fluoro
sulfinic acid

Quality Level

100

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT8102
MKCB4125
MKBV7891V
MKBT1542V
MKBS4845V

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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

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