4,4'-Thiodianiline

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4,4'-Thiodianiline
4,4'-Thiodianiline.svg
Names
IUPAC name
4-(4-Aminophenyl)sulfanylaniline
Other names
p,p′-Thiodianiline; Bis(4-aminophenyl) sulfide; 4,4'-Thioaniline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.883
EC Number 205-370-9
KEGG
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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Infobox references

4,4'-Thiodianiline (TDA) is an aromatic amine which is presumed to be carcinogenic to humans.

Chemical structure and properties[edit]

TDA is not combustible, but when heated it may decompose to form irritating and toxic fumes. An analogue of TDA is dapsone.

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.

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.

References[edit]

  1. ^ Hodgson, Herbert Henry. "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. Wiley-VCH. 27 (3): 3261–3263. doi:10.1002/cber.189402703119. Retrieved 11 February 2016.