1,1'-Thiocarbonyldiimidazole

HCID 80264CAS 6160-65-2
Substructure searchFind similar structures

Basic information

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 properties

XLogP
0.7
Topological polar surface area
67.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
12

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.

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 3 items

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
Signal word
Warning

Chemistry & industry

Applications · 3 items

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

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Related reactions

568 records
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Linked notes

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