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790184

Sodium 1-(trifluoromethyl)cyclopropanesulfinate

Name: Sodium 1-(trifluoromethyl)cyclopropanesulfinate
Brand: ALDRICH

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

Form:

solid

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Properties

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

functional group

fluoro, sulfinic acid

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

Description

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

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

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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Articles

Baran Diversinates™

Rapidly diversify (hetero)aromatic scaffolds for chemical industry needs amid resource and time constraints, ensuring efficiency.

Metabolically Stable tert-Butyl Replacement.

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

Global Trade Item Number

SKU	GTIN
790184-500MG	04061833231951
790184-5G	04061833332702