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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:82374 ☒N
ChEMBL
  • ChEMBL348856 ☒N
ChemSpider
  • 8435 ☒N
ECHA InfoCard 100.004.883 Edit this at Wikidata
EC Number
  • 205-370-9
KEGG
  • C19303 ☒N
PubChem CID
  • 8765
UNII
  • 6GGU990BQF checkY
CompTox Dashboard (EPA)
  • DTXSID9021344 Edit this at Wikidata
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 ☒N
    Key: ICNFHJVPAJKPHW-UHFFFAOYSA-N ☒N
  • 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).
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Infobox references
Chemical compound

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

  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.