4,4′-Thiodianiline (TDA) is the

organosulfur compound Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...

with the formula (H2NC6H4)2S. It is classified as a diamine and a

thioether In organic chemistry, a sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity as shown on right. Like many other sulfur-containing compounds, Volatile organic compound, volatile sulfides have ...

. 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 Sulfur ( American spelling and the preferred IUPAC name) or sulphur ( Commonwealth spelling) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms ...

is boiled in excess

aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...

over several hours to produce three isomers (1,1′; 1,4; 4,4′) of TDA. 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 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.

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

4,4'-Oxydianiline 4,4′-Oxydianiline (ODA) is an organic compound with the chemical formula, formula Oxygen, O(Carbon, C6Hydrogen, H4Nitrogen, NH2)2. It is an ether derivative of aniline. This colourless solid is a useful monomer and Cross-link, cross-linking agent ...

4,4'-Methylenedianiline 4,4′-Methylenedianiline (MDA) is an organic compound with the formula . It is a colorless solid, although commercial samples can appear yellow or brown. It is produced on an industrial scale, mainly as a precursor to polyurethanes. Synthesi ...

* Dapsone

References

{{DEFAULTSORT:Thiodianiline, 4, 4- Anilines Carcinogens Thioethers