Chemistry:3,4-Toluenedithiol

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3,4-Toluenedithiol is an organosulfur compound with the formula CH
3
C
6
H
3
(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.[1] 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) CH
3
C
6
H
3
(SO
2
Cl)
2
with tin.[2]

It has been investigated as a probe of thiol-disulfide reactions.[3]

"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.[4]

References

  1. 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. 
  2. 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. 
  3. 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. PMID 21205617. 
  4. 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. doi:10.1021/ed036p390. Bibcode1959JChEd..36..390C.