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[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.

[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.

[1]

[2]

[3]