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6160-65-2 molecular structure
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1-(1H-imidazole-1-carbothioyl)-1H-imidazole

ChemBase ID: 67483
Molecular Formular: C7H6N4S
Molecular Mass: 178.21434
Monoisotopic Mass: 178.03131721
SMILES and InChIs

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

Cite this record

CBID:67483 http://www.chembase.cn/molecule-67483.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
6160-65-2
EC Number
228-183-4
MDL Number
MFCD00005289
Beilstein Number
609349
PubChem SID
24849589
24889111
162033218
24889110
PubChem CID
80264

CALCULATED PROPERTIES

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 cm3
Polarizability 18.80097 Å3 Polar Surface Area 35.64 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
Apperance
Yellow Solid expand Show data source
Melting Point
101 - 103°C expand Show data source
80-82°C expand Show data source
98-102 °C expand Show data source
98-102 °C(lit.) expand Show data source
98-102°C expand Show data source
98-102°C expand Show data source
Hydrophobicity(logP)
0.978 expand Show data source
Storage Condition
Refrigerator, Under Inert Atmosphere expand Show data source
Storage Warning
Harmful/Moisture Sensitive/Keep Cold/Store under Argon expand Show data source
IRRITANT expand Show data source
Moisture Sensitive expand Show data source
European Hazard Symbols
X expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
Safety Statements
26-36/37 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Hazard statements
H301-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥90% (S) expand Show data source
≥95.0% (S) expand Show data source
90% expand Show data source
95% expand Show data source
95+% expand Show data source
97% expand Show data source
tech 90% expand Show data source
Grade
technical expand Show data source
technical grade expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C7H6N4S expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - 88545 external link
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 external link
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 external link
1,1’-Thiocarbonyldiimidazole can be used to deoxygenate carboxylic monosaccharide analogues.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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