1,1'-Thiocarbonyldiimidazole
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Basic information
- CAS
6160-65-2- Standard SMILES
S=C(n1ccnc1)n1ccnc1- InChIKey
RAFNCPHFRHZCPS-UHFFFAOYSA-N- Molecular formula
- C7H6N4S
- Average molar mass
- 178.22 g/mol
- Monoisotopic mass
- 178.03131719
Names & identifiers
- Preferred name
- 1,1'-Thiocarbonyldiimidazole
- IUPAC
- di(imidazol-1-yl)methanethione
- English name
- 1,1'-Thiocarbonyldiimidazole
- Molecular formula
- C7H6N4S
- Molecular weight
- 178.21
Names & synonyms
1,1'-ThiocarbonyldiimidazoleRefChem:8977676160-65-2ThiocarbonyldiimidazoleN,N'-Thiocarbonyldiimidazoledi(imidazol-1-yl)methanethionedi(1H-imidazol-1-yl)methanethione1,1-ThiocarbonyldiimidazoleMFCD000052891H-Imidazole, 1,1'-carbonothioylbis-N,N-ThiocarbonyldiimidazoleTCDI
Show more names
Thiocarbonyl diimidazolebis(1H-imidazol-2-yl)methanethioneDiiMidazdiimidazoL1,1'-THIOCARBONYL1,1'-Thiocarbonyldii
Thiocarbonylbisimidazole1,1'-Thiocarbonylbis(imidazole)Di-1H-imidazol-1-ylmethanethione1,1'-Carbonothioylbis-1H-imidazoleH8A75XB5AY1,1'-(Thiocarbonyl)diimidazole1-(1H-imidazole-1-carbothioyl)-1H-imidazoledi-1H-imidazol-1-ylmethanethion
Database identifiers
- CAS
6160-65-2- PubChem CID
- 80264
- DTXSID
DTXSID70210614- UNII
- H8A75XB5AY
- EC Number
- 228-183-4
- Nikkaji
- J5.204C
Properties
Computed structural propertiesFilling in
- XLogP
- 0.7
- Topological polar surface area
- 67.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 166
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Imidazoles
Physical DescriptionYellow powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 98 · 98-102 °C(lit.)
- Boiling point
- 342 °C · 342°C (rough estimate)
- Density
- 1.3046 · 1.3046 (rough estimate)
- refractive index
- 1.55 · 1.5500 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in terahydrofuran, toluene and dichloromethane.
- pka
- 1.96 · 1.96±0.10(Predicted)
- form
- Powder
- color
- Bright yellow
- Water Solubility
- decomposes
- Sensitive
- Moisture Sensitive
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 6.7% (1 of 15) of reports.
Warning
H302 (53.3%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 15 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1H-Imidazole, 1,1'-carbonothioylbis-
Status: No longer Valid Update: 03-12-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/32005
1H-Imidazole, 1,1'-carbonothioylbis-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazards SummaryAn irritant; Harmful by ingestion; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (53.3%)
Safety data
- F
- 9-21
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29332900
- risk_code
- 22-34
Chemistry & industry
Applications
Description1,1'-Thiocarbonyldiimidazole (TCDI) is an imidazole compound that can be prepared by reacting thiophosphoryl chloride with two corresponding imidazoles. Its structure has two imidazole rings, and the imidazole groups can be rapidly displaced, making it a safer alternative to thiophosphoryl chloride. TCDI is used as an organic synthesis or chemical reaction reagent for the synthesis of thiosemicarbazones and thioamides. It is also used in the Corey-Winter olefin synthesis and in the Barton-McCombie deoxygenation reaction. In addition, it is the sulfur analogue of the peptide addition reagent carbodiimidazole (CDI), which is used to couple peptides.
Uses1,1'-Thiocarbonyldiimidazole is used as a reagent for the deoxygenation of alcohols with tributyltin hydride and diols with lithium aluminum hydride. It is also used to deoxygenate carboxylic monosaccharide analogues. Further, it is a useful reagent involved in biochemical synthesis. In addition to this, it is used to prepare 1-[bis-(4-methoxy-phenyl)-methyl]-1H-imidazole by reacting with 4,4'-dimethoxy-benzhydrol.
Uses1,1’Thiocarbonyldiimidazole can be used to deoxygenate carboxylic monosaccharide analogues.
Upstream & downstream products
Downstream products
Related reactions
568 records
Compound notes
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