CAS 6160-65-2|1-(1H-imidazole-1-carbothioyl)-1H-imidazole|1,1'-Thiocarbonyldiimidazole|1-(imidazole-1-carbothioyl)imidazole|1,1'-Thiocarbonyldi(1H-imidazole) 90%|Di(1H-imidazol-1-yl)methanethione|N,N...

General Information

Structure

Molecular Formula

C₇H₆N₄S

Molecular Mass

178.21434

Exact Mass

178.03131721

Charge

InChI

InChI=1S/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H

InChIKey

RAFNCPHFRHZCPS-UHFFFAOYSA-N

Canonic Smiles

S=C(n1cncc1)n1cncc1

Isomeric Smiles

C(=S)(n1cncc1)n1cncc1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-0.0659748

LogD (pH = 7.4)

-0.06423997

Log P

-0.06421781

Molar Refractivity

48.7679

Polarizability

18.80097

Polar Surface Area

35.64

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

1-(1H-imidazole-1-carbothioyl)-1H-imidazole

Synonyms

1,1'-Thiocarbonyldiimidazole1,1'-Thiocarbonyldi(1H-imidazole) 90%Di(1H-imidazol-1-yl)methanethioneN,N′-硫羰基二咪唑1,1′-ThiocarbonyldiimidazoleN,N'-Thiocarbonyldiimidazole1,1'-(Thiocarbonyl)bis[imidazole]di-1H-Imidazol-1-ylmethanethione1,1'-Carbonothioylbis-1H-imidazole1-[(1H-imidazol-1-yl)carbothioyl]-1H-imidazoleThiocarbonylbisimidazoleThiocarbonyldiimidazole1-(1H-Imidazol-1-ylcarbothioyl)-1H-imidazoleDiimidazol-1-ylmethanthione1,1'-(Thiocarbonyl)diimidazole, 1,1'-(Thiocarbonyl)diimidazoleNSC 1416921,1'-Thiocarbonyldiimidazole1,1'-硫代碳酰基二咪唑

IUPAC Traditional name

1-(imidazole-1-carbothioyl)imidazole

Names and Identifiers

Registration numbers

CAS Number

6160-65-2

MDL Number

MFCD00005289

PubChem SID

248891112484958916203321824889110

Beilstein Number

609349

EC Number

228-183-4

PubChem CID

80264

Registration numbers

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Sigma Aldrich

156051

Application
A useful reagent in biochemical synthesis.
Reagent used for the deoxygenation of alcohols with tributyltin hydride and diols with lithium aluminum hydride.
Packaging
5, 10 g in glass bottle

88545

Other Notes
Reagent for the synthesis of thioamides1; Used in a modified Corey-Winter olefin synthesis2; Preparation of thiocarbamates from alcohols which undergo radical reactions with Bu3SnH-AIBN3,4
Packaging
1, 5, 25 g in glass bottle

TRC

T344410

1,1’-Thiocarbonyldiimidazole can be used to deoxygenate carboxylic monosaccharide analogues.

Molecule Details

References

PubChem Literature

From Data Sources

• Loke, I., et al.: Tetrahedron, 68, 697 (2012)

• Reacts with diols to give cyclic thionocarbonates which are desulfurized by trialkyl phosphites to give alkenes by cis-elimination of CO₂ from the intermediate carbene (Corey-Winter olefination): J. Am. Chem. Soc., 85, 2677 (1963); Angew. Chem. Int. Ed., 14, 753 (1975). For a modified procedure involving ring-opening of the thionocarbonate intermediate with an alkyl iodide, followed by Zn reduction of the resulting iodo ester, see: Tetrahedron Lett., 3793 (1973). Alternatively, the thionocarbonate of a 1,2-diol can be selectively reduced to the methylenedioxy group with Triphenyltin hydride, L00163, under free-radical conditions: J. Org. Chem., 62, 4159 (1997).

• Can be used to deoxygenate carbocyclic monosaccharide analogues: Tetrahedron., 48, 2349 (1992).

References

Bioactivity

PubChem BioAssay

Bioactivity