4,5-Dichloro-1,2,3-dithiazolium chloride

4,5-Dichloro-1,2,3-dithiazolium chloride
Names
	Other names Appel's salt
Identifiers
CAS Number	75318-43-3;
3D model (JSmol)	Interactive image;
ChemSpider	9270989;
PubChem CID	11095847;
UNII	156NP9484D;
CompTox Dashboard (EPA)	DTXSID30455049 ;
	InChI InChI=1S/C2Cl2NS2.ClH/c3-1-2(4)6-7-5-1;/h;1H/q+1;/p-1 Key: NIZMCFUMSHISLW-UHFFFAOYSA-M;
	SMILES C1(=NS[S+]=C1Cl)Cl.[Cl-];
Properties
Chemical formula	C2Cl3NS2
Molar mass	208.50 g·mol−1
Appearance	green solid
Melting point	172 °C (342 °F; 445 K) decomposition
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4,5-Dichloro-1,2,3-dithiazolium chloride (Appel's salt) is an organosulfur compound. It is the chloride salt of the 4,5-dichloro-1,2,3-dithiazolium cation. It is a green solid that is poorly soluble in organic solvents.^[1]

Synthesis

The compound is obtained by the reaction of acetonitrile with sulfur monochloride. The initial phases of this reaction entail chlorination of the acetonitrile. The resulting dichloroacetonitrile undergoes cycloaddition with sulfur monochloride:^[1]

Cl₂CHCN + S₂Cl₂ → [S₂NC₂Cl₂]Cl + HCl

The cation is highly electrophilic. It hydrolyzes readily. Protic nucleophiles displace one chloride:^[2]^[3]

[S₂NC₂Cl₂]Cl + 2 RNH₂ → S₂NC₂Cl(=NR) + [RNH₃]Cl

The compound was discovered by Appel et al.^[4]

References

^ ^a ^b Rees, Charles W. (1992). "Polysulfur-Nitrogen Heterocyclic Chemistry". Journal of Heterocyclic Chemistry. 29 (3): 639–651. doi:10.1002/jhet.5570290306.
^ Foucourt, Alicia; Chosson, Elizabeth; Besson, Thierry (2009). "4,5-Dichloro-1,2,3-dithiazol-1-ium Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01113. ISBN 978-0471936237.
^ Cuadro, Ana M.; Alvarez-Buila, Julio (1994). "4,5-Dichloro-1,2,3-dithiazolium chloride (Appel's Salt): Reactions with N-Nucleophiles". Tetrahedron. 50 (33): 10037–10046. doi:10.1016/S0040-4020(01)89619-8. hdl:10017/3581.
^ Appel, Rolf; Janssen, Heinrich; Siray, Mustafa; Knoch, Falk (1985). "Synthese und Reaktionen des 4,5-Dichlor-1,2,3-dithiazolium-chlorids". Chemische Berichte. 118 (4): 1632–1643. doi:10.1002/cber.19851180430.

[Rees-1] Rees, Charles W. (1992). "Polysulfur-Nitrogen Heterocyclic Chemistry". Journal of Heterocyclic Chemistry. 29 (3): 639–651. doi:10.1002/jhet.5570290306.

[2] Foucourt, Alicia; Chosson, Elizabeth; Besson, Thierry (2009). "4,5-Dichloro-1,2,3-dithiazol-1-ium Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01113. ISBN 978-0471936237.

[3] Cuadro, Ana M.; Alvarez-Buila, Julio (1994). "4,5-Dichloro-1,2,3-dithiazolium chloride (Appel's Salt): Reactions with N-Nucleophiles". Tetrahedron. 50 (33): 10037–10046. doi:10.1016/S0040-4020(01)89619-8. hdl:10017/3581.

[4] Appel, Rolf; Janssen, Heinrich; Siray, Mustafa; Knoch, Falk (1985). "Synthese und Reaktionen des 4,5-Dichlor-1,2,3-dithiazolium-chlorids". Chemische Berichte. 118 (4): 1632–1643. doi:10.1002/cber.19851180430.

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