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901415

Sigma-Aldrich

N-(tert-Butyl)-N-((ethoxycarbonothioyl)thio)-3,5-bis(trifluoromethyl)benzamide

Synonym(s):

Alexanian xanthylation reagent

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About This Item

Empirical Formula (Hill Notation):
C16H17F6NO2S2
CAS Number:
2022988-45-8
Molecular Weight:
433.43
UNSPSC Code:
12352111
NACRES:
NA.22

form

solid

Quality Level

100

mp

40-46 °C

functional group

amine
fluoro

storage temp.

−20°C

Application

As reported by the Alexanian. laboratory, this reagent is used for site-selective, intermolecular C-H xanthylation of alkanes, leading to the rapid diversification of otherwise inert C-H bonds. Once installed, the xanthate group provides direct access to diverse product analogues via several aliphatic C-H transformations, including halogenation, deuteration, vinylation, and hydroxylation. Product is best stored in foil-wrapped vials in the freezer when not in use; however, it can be weighed out on the bench without risk of decomposition. This product is offered collaboratively with UNC-Chapel Hill and Erik Alexanian.

Other Notes

C–H Xanthylation: A Synthetic Platform for Alkane Functionalization.

Storage Class Code

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
MKCS9893
MKCL8234
MKCG4174

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William L Czaplyski et al.
Journal of the American Chemical Society (2016-10-16)
Intermolecular functionalizations of aliphatic C-H bonds offer unique strategies for the synthesis and late-stage derivatization of complex molecules, but the chemical space accessible remains limited. Herein, we report a transformation significantly expanding the chemotypes accessible via C-H functionalization. The C-H

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