88545
1,1′-Thiocarbonyldiimidazole
≥95.0% (S)
Synonym(s):
TCDI
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About This Item
Empirical Formula (Hill Notation):
C7H6N4S
CAS Number:
Molecular Weight:
178.21
Beilstein:
609349
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
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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
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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Direct coupling of indoles with carbonyl compounds: short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families.
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Journal of the American Chemical Society, 126(24), 7450-7451 (2004)
1, 1?-Thiocarbonyldiimidazole.
e-EROS Encyclopedia of Reagents for Organic Synthesis (2001)
Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach.
Richter JM, et al.
Journal of the American Chemical Society, 130(52), 17938-17954 (2008)
S. Hanessian et al.
Canadian Journal of Chemistry, 65, 1859-1859 (1987)
E. Vedejs et al.
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