2-Imidazolidinethione

2-Imidazolidinethione
Names
	Preferred IUPAC name 1,5-Dihydro-2H-imidazole-2-thione
	Other names 2-Mercaptoimidazole
Identifiers
CAS Number	872-35-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3260774;
ChemSpider	1013196;
EC Number	212-823-4;
PubChem CID	1201386;
UNII	FD37BLD6L2;
CompTox Dashboard (EPA)	DTXSID6061236 ;
	InChI InChI=1S/C3H4N2S/c6-3-4-1-2-5-3/h1-2H,(H2,4,5,6) Key: OXFSTTJBVAAALW-UHFFFAOYSA-N;
	SMILES C1=CNC(=S)N1;
Properties
Chemical formula	C3H4N2S
Molar mass	100.14 g·mol−1
Appearance	white solid
Melting point	225–227 °C (437–441 °F; 498–500 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds	Ethylene thiourea, Aminothiazole, 1,3-Dihydroimidazol-2-one (2-hydroxyimidazole)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Imidazolidinethione is the organosulfur compound with the formula C₂H₂(NH)₂C=S. It is a cyclic unsaturated thiourea with a short C=S bond length of 169 pm.^[1] The compound is often referred to as 2-mercaptoimidazole, which is a tautomer that is not observed. The compound forms a variety of metal complexes.^[2] In terms of bonding and reactivity, 2-imidazolidinethione is similar to mercaptobenzimidazole.

References

^ Owczarzak, Agata; Dutkiewicz, Zbigniew; Kurczab, Rafał; Pietruś, Wojciech; Kubicki, Maciej; Grześkiewicz, Anita M. (2019). "Role of Staple Molecules in the Formation of S···S Contact in Thioamides: Experimental Charge Density and Theoretical Studies". Crystal Growth & Design. 19 (12): 7324–7335. doi:10.1021/acs.cgd.9b01204. S2CID 208708412.
^ Lobana, Tarlok S.; Sharma, Renu; Sharma, Rekha; Butcher, Ray J. (2008). "Metal Derivatives of Heterocyclic Thioamides: Synthesis and Crystal Structures of Copper Complexes with 1-Methyl-1,3-imidazoline-2-thione and 1,3-Imidazoline-2-thione". Zeitschrift für Anorganische und Allgemeine Chemie. 634 (10): 1785–1790. doi:10.1002/zaac.200800161.

[1] Owczarzak, Agata; Dutkiewicz, Zbigniew; Kurczab, Rafał; Pietruś, Wojciech; Kubicki, Maciej; Grześkiewicz, Anita M. (2019). "Role of Staple Molecules in the Formation of S···S Contact in Thioamides: Experimental Charge Density and Theoretical Studies". Crystal Growth & Design. 19 (12): 7324–7335. doi:10.1021/acs.cgd.9b01204. S2CID 208708412.

[2] Lobana, Tarlok S.; Sharma, Renu; Sharma, Rekha; Butcher, Ray J. (2008). "Metal Derivatives of Heterocyclic Thioamides: Synthesis and Crystal Structures of Copper Complexes with 1-Methyl-1,3-imidazoline-2-thione and 1,3-Imidazoline-2-thione". Zeitschrift für Anorganische und Allgemeine Chemie. 634 (10): 1785–1790. doi:10.1002/zaac.200800161.

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