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679712

Sigma-Aldrich

S-Methyl N-(2,2,2-trichloroethoxysulfonyl)carbonchloroimidothioate

97%

Synonym(s):

N-(2,2,2-Trichloroethoxysulfonyl)carbonchlorothioic acid S methyl ester

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About This Item

Empirical Formula (Hill Notation):
C4H5Cl4NO3S2
CAS Number:
882739-48-2
Molecular Weight:
321.03
MDL number:
MFCD20730839
UNSPSC Code:
12352101
PubChem Substance ID:
24885510
NACRES:
NA.22

assay

97%

form

solid

mp

75-79 °C

functional group

chloro
thioether

SMILES string

CS\C(Cl)=N\S(=O)(=O)OCC(Cl)(Cl)Cl

InChI

1S/C4H5Cl4NO3S2/c1-13-3(5)9-14(10,11)12-2-4(6,7)8/h2H2,1H3/b9-3+

InChI key

NGCLYHLLOXVGSU-YCRREMRBSA-N

Application

Reactant for preparation of:
  • Muramycin analogs as antibacterial agents against drug-resistant bacteria
  • L-epicapreomycidine using rhodium-catalyzed stereoselective oxidative cyclization
  • (+)-gonyautoxin 3 via Rh-catalyzed amination
  • (+)-monobromophakellin and (+)-phakellin via a strategy applicable to synthesis of more complex members of this family of marine sponge-derived alkaloids including palau′amine
  • 2-imidazolidinones and 2-imino-1,3-imidazolidines
Reagent for preparation of protected guanidine derivatives.[1]

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC1187V
07029AH

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Mihyong Kim et al.
Organic letters, 8(6), 1073-1076 (2006-03-10)
[reaction: see text] Oxidative C-H amination of N-trichloroethoxysulfonyl-protected ureas and guanidines is demonstrated to proceed in high yield for tertiary and benzylic-derived substrates. The success of these reactions is predicated on the choice of the electron-withdrawn 2,2,2-trichloroethoxysulfonyl (Tces) protecting group

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