4,4'-Thiodianiline

4,4′-Thioaniline
Names
	Preferred IUPAC name 4,4′-Sulfanediyldianiline
	Other names p,p′-Thiodianiline; Bis(4-aminophenyl) sulfide; 4,4′-Thioaniline; 4-(4-Aminophenyl)sulfanylaniline
Identifiers
CAS Number	139-65-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82374 ;
ChEMBL	ChEMBL348856 ;
ChemSpider	8435 ;
ECHA InfoCard	100.004.883
EC Number	205-370-9;
KEGG	C19303 ;
PubChem CID	8765;
UNII	6GGU990BQF ;
CompTox Dashboard (EPA)	DTXSID9021344 ;
	InChI InChI=1S/C12H12N2S/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2 Key: ICNFHJVPAJKPHW-UHFFFAOYSA-N ;
	SMILES C1=CC(=CC=C1N)SC2=CC=C(C=C2)N;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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

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

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

TDA is no longer produced in the USA.

Toxicity

TDA has caused mutations in some strains of Salmonella typhimurium and has caused tumors in laboratory mice and rats.

Related compounds

References

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.

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[Hodgson-1] 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.

[2] Nietzki, R; Bothof, Heinrich (1894). "The Understanding of Thioanilines". Reports of the German Chemical Society. 27 (3): 3261–3263. doi:10.1002/cber.189402703119.

[3] 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.