3,4-Dichloro-1,2,5-thiadiazole

3,4-Dichloro-1,2,5-thiadiazole
Identifiers
CAS Number	5728-20-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	72097;
ECHA InfoCard	100.024.757
EC Number	227-232-7;
PubChem CID	79804;
UNII	PE8RVW5SWM;
CompTox Dashboard (EPA)	DTXSID00205896 ;
	InChI InChI=1S/C2Cl2N2S/c3-1-2(4)6-7-5-1 Key: YNZQOVYRCBAMEU-UHFFFAOYSA-N;
	SMILES C1(=NSN=C1Cl)Cl;
Properties
Chemical formula	C2Cl2N2S
Molar mass	155.00 g·mol−1
Density	1.648 g/cm3
Boiling point	158 °C (316 °F; 431 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H335, H412
Precautionary statements	P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3,4-Dichloro-1,2,5-thiadiazole is the heterocycle with the formula Cl₂C₂N₂S. It is a colorless liquid. The compound is produced by treating cyanogen with disulfur dichloride.^[1] The compound can also be prepared from aminoacetonitrile.^[2]

It is a planar molecule consisting of a thiadiazole core with two chlorine atoms as substituents. The chloride groups are displaced readily by ammonia to give the diamine:^[3]

Cl₂C₂N₂S + 4 NH₃ → (H₂N)₂C₂N₂S + 2 NH₄Cl

Related compounds

2,1,3-Benzothiadiazole, C₆H₄N₂S, derived from 1,2-diaminobenzene

References

^ Gail, Ernst; Gos, Stephen; Kulzer, Rupprecht; Lorösch, Jürgen; Rubo, Andreas; Sauer, Manfred; Kellens, Raf; Reddy, Jay; Steier, Norbert; Hasenpusch, Wolfgang (2011). "Cyano Compounds, Inorganic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_159.pub3. ISBN 978-3-527-30385-4.
^ Weinstock, Leonard M.; Davis, Paul; Handelsman, Barry; Tull, Roger J. (1967). "General Synthetic System for 1,2,5-Thiadiazoles". The Journal of Organic Chemistry. 32 (9): 2823–2829. doi:10.1021/jo01284a040.
^ Komin, Andrew P.; Carmack, Marvin (1976). "The chemistry of 1,2,5-thiadiazoles V. Synthesis of 3,4-Diamino-1,2,5-thiadiazole and [1,2,5] Thiadiazolo[3,4-b ]pyrazines". Journal of Heterocyclic Chemistry. 13: 13–22. doi:10.1002/jhet.5570130102.

[1] Gail, Ernst; Gos, Stephen; Kulzer, Rupprecht; Lorösch, Jürgen; Rubo, Andreas; Sauer, Manfred; Kellens, Raf; Reddy, Jay; Steier, Norbert; Hasenpusch, Wolfgang (2011). "Cyano Compounds, Inorganic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_159.pub3. ISBN 978-3-527-30385-4.

[2] Weinstock, Leonard M.; Davis, Paul; Handelsman, Barry; Tull, Roger J. (1967). "General Synthetic System for 1,2,5-Thiadiazoles". The Journal of Organic Chemistry. 32 (9): 2823–2829. doi:10.1021/jo01284a040.

[3] Komin, Andrew P.; Carmack, Marvin (1976). "The chemistry of 1,2,5-thiadiazoles V. Synthesis of 3,4-Diamino-1,2,5-thiadiazole and [1,2,5] Thiadiazolo[3,4-b ]pyrazines". Journal of Heterocyclic Chemistry. 13: 13–22. doi:10.1002/jhet.5570130102.

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