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88545 Sigma-Aldrich

1,1′-Thiocarbonyldiimidazole

≥95.0% (S)

Synonym: TCDI

  • CAS Number 6160-65-2

  • Empirical Formula (Hill Notation) C7H6N4S

  • Molecular Weight 178.21

  •  Beilstein/REAXYS Number 609349

  •  EC Number 228-183-4

  •  MDL number MFCD00005289

  •  PubChem Substance ID 57653315

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Properties

Related Categories Carbonyldiimidazole Derivatives, Chemical Synthesis, Coupling, Synthetic Reagents
InChI Key   RAFNCPHFRHZCPS-UHFFFAOYSA-N
assay   ≥95.0% (S)
mp   98-102 °C (lit.)
storage temp.   2-8°C

Description

Application

• 1,1′-Thiocarbonyldiimidazole (TCDI) is generally used as a reagent to carry out the deoxygenation of vicinal diols by forming cyclic thionocarbonate in Corey-Winter alkene synthesis.
• It is used as a reagent in the enantioselective total synthesis of (+)-hapalindole Q, 12-epi-fischerindole U and welwitindolinone A.
• It is also used in the preparation of trithiocarbonates, xanthates, and dithiocarbamates as chain transfer agents for the reversible addition fragmentation chain transfer and macromolecular design (RAFT/ MADIX) polymerization.

Packaging

1, 5, 25 g in glass bottle

Other Notes

Reagent for the synthesis of thioamides; Used in a modified Corey-Winter olefin synthesis; Preparation of thiocarbamates from alcohols which undergo radical reactions with Bu3SnH-AIBN

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis

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Protocols & Articles
Peer-Reviewed Papers
15

References

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