3,4-Toluenedithiol

3,4-Toluenedithiol
Names
	Other names 1-toluene-3,4-dithiol, dithiol
Identifiers
CAS Number	496-74-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	9910;
ECHA InfoCard	100.007.118
EC Number	207-828-3;
PubChem CID	10334;
UNII	U89B11P7SC;
CompTox Dashboard (EPA)	DTXSID7060093 ;
	InChI InChI=1S/C7H8S2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3 Key: NIAAGQAEVGMHPM-UHFFFAOYSA-N;
	SMILES CC1=CC(=C(C=C1)S)S;
Properties
Chemical formula	C7H8S2
Molar mass	156.26 g·mol−1
Appearance	colorless solid
Melting point	29 °C (84 °F; 302 K)
Boiling point	185–187 °C (365–369 °F; 458–460 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H318, H335
Precautionary statements	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+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-Toluenedithiol is an organosulfur compound with the formula CH₃C₆H₃(SH)₂. It is encountered as a colorless wax or oil. The compound is classified as an aromatic dithiol. It forms brightly colored derivatives with many metal ions.^[2] The compound is closely related to 1,2-benzenedithiol but is often more widely used because it is less expensive. 3,4-Toluenedithiol is prepared by reduction of the bis(sulfonyl chloride) CH₃C₆H₃(SO₂Cl)₂ with tin.^[3]

It has been investigated as a probe of thiol-disulfide reactions.^[4]

"Dithiol"

Under the name "dithiol", 3,4-toluenedithiol was popularized as a reagent in qualitative inorganic analysis. It was promoted as an alternative to hydrogen sulfide since it also forms colorful solid precipitates with a variety of metal ions.^[5]

References

^ "Toluene-3,4-dithiol". pubchem.ncbi.nlm.nih.gov. Retrieved 12 March 2024.
^ Paw, Witold; Cummings, Scott D.; Adnan Mansour, M.; Connick, Williams B.; Geiger, David K.; Eisenberg, Richard (1998). "Luminescent platinum complexes: Tuning and using the excited state". Coordination Chemistry Reviews. 171: 125–150. doi:10.1016/s0010-8545(98)90023-6.
^ Mills, William H.; Clark, Robert E. D. (1936). "35. Stereochemistry of some new complex thio-salts of mercury, cadmium, and zinc". Journal of the Chemical Society (Resumed): 175. doi:10.1039/jr9360000175.
^ Dietz, Karl-Josef; Pfannschmidt, Thomas (2011). "Novel Regulators in Photosynthetic Redox Control of Plant Metabolism and Gene Expression". Plant Physiology. 155 (4): 1477–1485. doi:10.1104/pp.110.170043. PMC 3091116. PMID 21205617.
^ Clark, R. E. D.; Neville, R. C. (1959). "Toluene-3,4-dithiol and Its Derivatives as Analytical Reagents: A New Approach to Qualitative Inorganic Analysis". Journal of Chemical Education. 36 (8): 390. Bibcode:1959JChEd..36..390C. doi:10.1021/ed036p390.

[1] "Toluene-3,4-dithiol". pubchem.ncbi.nlm.nih.gov. Retrieved 12 March 2024.

[2] Paw, Witold; Cummings, Scott D.; Adnan Mansour, M.; Connick, Williams B.; Geiger, David K.; Eisenberg, Richard (1998). "Luminescent platinum complexes: Tuning and using the excited state". Coordination Chemistry Reviews. 171: 125–150. doi:10.1016/s0010-8545(98)90023-6.

[3] Mills, William H.; Clark, Robert E. D. (1936). "35. Stereochemistry of some new complex thio-salts of mercury, cadmium, and zinc". Journal of the Chemical Society (Resumed): 175. doi:10.1039/jr9360000175.

[4] Dietz, Karl-Josef; Pfannschmidt, Thomas (2011). "Novel Regulators in Photosynthetic Redox Control of Plant Metabolism and Gene Expression". Plant Physiology. 155 (4): 1477–1485. doi:10.1104/pp.110.170043. PMC 3091116. PMID 21205617.

[5] Clark, R. E. D.; Neville, R. C. (1959). "Toluene-3,4-dithiol and Its Derivatives as Analytical Reagents: A New Approach to Qualitative Inorganic Analysis". Journal of Chemical Education. 36 (8): 390. Bibcode:1959JChEd..36..390C. doi:10.1021/ed036p390.

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