4,4'-Thiodianiline
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Preferred IUPAC name
4,4′-Sulfanediyldianiline | |
Other names
p,p′-Thiodianiline; Bis(4-aminophenyl) sulfide; 4,4′-Thioaniline; 4-(4-Aminophenyl)sulfanylaniline
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.883 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C12H12N2S | |
Molar mass | 216.3 g/mol |
Appearance | Brown-brown violet powder or needles |
Density | 1.26 g/cm3 |
Melting point | 105 to 107 °C (221 to 225 °F; 378 to 380 K) |
Boiling point | 464.8 °C (868.6 °F; 738.0 K) @ 760mmHg |
Hazards | |
Flash point | 234.9 °C (454.8 °F; 508.0 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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4,4′-Thiodianiline (TDA) is the organosulfur compound with the formula (H2NC6H4)2S. It is classified as a diamine and a thioether. It typically appears as an (off-)white solid powder. An analogue of TDA is the drug dapsone, for which the sulphur species is oxidised.
Synthesis
[edit]Sulfur is boiled in excess aniline over several hours to produce three isomers (1,1′; 1,4; 4,4′) of TDA.[1] The same journal documents syntheses of similar and overlapping compounds by Merz and Weith in 1871, and K. A. Hoffman in 1894. A study by Nietzki and Bothof[2] shows indications that including an oxide of lead may maximize the yield of the 4,4′ variant that this page refers to.
Uses
[edit]TDA was used as a chemical intermediate in the production of three dyes: CI mordant yellow 16, milling red G and milling red FR, as well as the medicine Dapsone. TDA has also been used in the synthesis of polyimine vitrimers.[3]
Production
[edit]TDA is no longer produced in the USA.
Toxicity
[edit]TDA has caused mutations in some strains of Salmonella typhimurium and has caused tumors in laboratory mice and rats.
Related compounds
[edit]References
[edit]- ^ Hodgson, Herbert Henry (January 1924). "Direct sulphuration of aniline". J. Chem. Soc., Trans. 1924 (125): 1855–1858. doi:10.1039/CT9242501855. Retrieved 11 February 2016.
- ^ Nietzki, R; Bothof, Heinrich (1894). "The Understanding of Thioanilines". Reports of the German Chemical Society. 27 (3): 3261–3263. doi:10.1002/cber.189402703119.
- ^ Schoustra, Sybren K.; Dijksman, Joshua A.; Zuilhof, Han; Smulders, Maarten M. J. (2021). "Molecular control over vitrimer-like mechanics – tuneable dynamic motifs based on the Hammett equation in polyimine materials". Chemical Science. 12 (1): 293–302. doi:10.1039/d0sc05458e. ISSN 2041-6520. PMC 8178953. PMID 34163597.