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

• ChemBase ID: 67483
• Molecular Formular: C7H6N4S
• Molecular Mass: 178.21434
• Monoisotopic Mass: 178.03131721
• SMILES: C(=S)(n1cncc1)n1cncc1
• Canonical SMILES: S=C(n1cncc1)n1cncc1
• InChI: InChI=1S/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H
• InChIKey: RAFNCPHFRHZCPS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(1H-imidazole-1-carbothioyl)-1H-imidazole
• IUPAC Traditional name: 1-(imidazole-1-carbothioyl)imidazole
• Synonyms: 1,1'-Thiocarbonyldiimidazole; di-1H-Imidazol-1-ylmethanethione; 1,1'-Carbonothioylbis-1H-imidazole; , 1,1'-(Thiocarbonyl)diimidazole; 1,1'-(Thiocarbonyl)bis[imidazole]; 1,1'-(Thiocarbonyl)diimidazole; 1-(1H-Imidazol-1-ylcarbothioyl)-1H-imidazole; Diimidazol-1-ylmethanthione; N,N'-Thiocarbonyldiimidazole; NSC 141692; Thiocarbonylbisimidazole; Thiocarbonyldiimidazole; 1-[(1H-imidazol-1-yl)carbothioyl]-1H-imidazole; 1,1′-Thiocarbonyldiimidazole; Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldi(1H-imidazole) 90%; 1,1'-Thiocarbonyldiimidazole; N,N′-硫羰基二咪唑; 1,1'-硫代碳酰基二咪唑

Database IDs

• CAS Number: 6160-65-2
• EC Number: 228-183-4
• MDL Number: MFCD00005289
• Beilstein Number: 609349
• PubChem SID: 162033218; 24889110; 24849589; 24889111
• PubChem CID: 80264

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.0659748
• LogD (pH = 7.4): -0.06423997
• Log P: -0.06421781
• Molar Refractivity: 48.7679 cm^3
• Polarizability: 18.80097 Å^3
• Polar Surface Area: 35.64 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Yellow Solid
• Melting Point: 101 - 103°C; 80-82°C; 98-102 °C; 98-102 °C(lit.); 98-102°C; 98-102°C
• Hydrophobicity(logP): 0.978

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: Harmful/Moisture Sensitive/Keep Cold/Store under Argon; IRRITANT; Moisture Sensitive
• European Hazard Symbols: X
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS06
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (S); ≥95.0% (S); 90%; 95%; 95+%; 97%; tech 90%
• Grade: technical; technical grade
• Empirical Formula (Hill Notation): C7H6N4S

DETAILS

Sigma Aldrich - 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

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

Toronto Research Chemicals - T344410

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

REFERENCES

• Loke, I., et al.: Tetrahedron, 68, 697 (2012)
• Can be used to deoxygenate carbocyclic monosaccharide analogues: Tetrahedron., 48, 2349 (1992).
• 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).