88545

1,1′-Thiocarbonyldiimidazole

≥95.0% (S)

• Synonym(s): TCDI
• Empirical Formula (Hill Notation): C₇H₆N₄S
• CAS Number: 6160-65-2
• Molecular Weight: 178.21
• Beilstein: 609349
• EC Number: 228-183-4
• MDL number: MFCD00005289
• UNSPSC Code: 12352005
• PubChem Substance ID: 57653315
• NACRES: NA.22

Properties

• Quality Level: 200
• Assay: ≥95.0% (S)
• form: powder
• reaction suitability: reaction type: Carbonylations
• mp: 98-102 °C (lit.)
• functional group: thiourea
• storage temp.: 2-8°C
• SMILES string: S=C(n1ccnc1)n2ccnc2
• InChI: 1S/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H
• InChI key: RAFNCPHFRHZCPS-UHFFFAOYSA-N

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.

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 Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302,H315,H319
• Precautionary Statements: P264 - P270 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves