88545
1,1′-Thiocarbonyldiimidazole
≥95.0% (S)
Synonym(s):
TCDI
Sign In to View Organizational & Contract Pricing.
Select a Size
About This Item
Empirical Formula (Hill Notation):
C7H6N4S
CAS Number:
Molecular Weight:
178.21
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
228-183-4
Beilstein/REAXYS Number:
609349
MDL number:
Assay:
≥95.0% (S)
Form:
powder
InChI key
RAFNCPHFRHZCPS-UHFFFAOYSA-N
InChI
1S/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H
SMILES string
S=C(n1ccnc1)n2ccnc2
assay
≥95.0% (S)
form
powder
reaction suitability
reaction type: Carbonylations
Quality Level
mp
98-102 °C (lit.)
functional group
thiourea
storage temp.
2-8°C
Looking for similar products? Visit Product Comparison Guide
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
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
T.V. RajanBabu et al.
Journal of the American Chemical Society, 111, 1759-1759 (1989)
E. Vedejs et al.
Tetrahedron Letters, 3793-3793 (1973)
Selective one-pot synthesis of trithiocarbonates, xanthates, and dithiocarbamates for use in RAFT/MADIX living radical polymerizations.
Wood MR, et al.
Organic Letters, 8(4), 553-556 (2006)
S. Hanessian et al.
Canadian Journal of Chemistry, 65, 1859-1859 (1987)
1, 1?-Thiocarbonyldiimidazole.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service