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88545

Sigma-Aldrich

1,1′-Thiocarbonyldiimidazole

≥95.0% (S)

Synonym(s):

TCDI

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About This Item

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

Quality Level

200

Assay

≥95.0% (S)

form

powder

reaction suitability

reaction type: Carbonylations

mp

98-102 °C (lit.)

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Direct coupling of indoles with carbonyl compounds: short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families.
Baran PS and Richter JM
Journal of the American Chemical Society, 126(24), 7450-7451 (2004)
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)
1, 1?-Thiocarbonyldiimidazole.
e-EROS Encyclopedia of Reagents for Organic Synthesis (2001)
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)
E. Vedejs et al.
Tetrahedron Letters, 3793-3793 (1973)
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