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Revision as of 11:59, 20 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'KEGG', 'CASNo').← Previous edit Latest revision as of 17:51, 26 February 2024 edit undoMarbletan (talk | contribs)Extended confirmed users5,256 edits no longer a stub 
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{{Chembox {{Chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 414639178 | verifiedrevid = 456502095
| Name = 4,4′-Thioaniline
| ImageFile = 4,4'-Thiodianiline.svg | ImageFile = 4,4'-Thiodianiline.svg
| ImageSize = 200px | ImageSize=
| ImageAlt = | ImageAlt =
| PIN = 4,4′-Sulfanediyldianiline
| IUPACName = 4-(4-Aminophenyl)sulfanylaniline
| OtherNames = ''p'',''p''′-Thiodianiline; Bis(4-aminophenyl) sulfide; 4,4'-Thioaniline | OtherNames = ''p'',''p''′-Thiodianiline; Bis(4-aminophenyl) sulfide; 4,4′-Thioaniline; 4-(4-Aminophenyl)sulfanylaniline
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 139-65-1 -->
| PubChem = 8765 | CASNo = 139-65-1
| UNII_Ref = {{fdacite|correct|FDA}}
| ChEMBL = <!-- blanked - oldvalue: 348856 -->
| UNII = 6GGU990BQF
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
| EINECS = 205-370-9
| KEGG = <!-- blanked - oldvalue: C19303 -->
| PubChem = 8765
⚫ | SMILES = C1=CC(=CC=C1N)SC2=CC=C(C=C2)N}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫ | Section2 = {{Chembox Properties
| ChEMBL = 348856
⚫ | Formula = C<sub>12</sub>H<sub>12</sub>N<sub>2</sub>S
| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫ | MolarMass = 216.3 g/mol
| ChEBI = 82374
⚫ | Appearance = Brown-brown violet powder or needles
| KEGG_Ref = {{keggcite|changed|kegg}}
⚫ | Density =1.26 g/cm<sup>3</sup>
| KEGG = C19303
| MeltingPt =105-107 °C
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| BoilingPt =464.8 °C @ 760mmHg
| Solubility = }} | ChemSpiderID = 8435
⚫ | SMILES = C1=CC(=CC=C1N)SC2=CC=C(C=C2)N
⚫ | Section3 = {{Chembox Hazards
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫ | MainHazards =
| StdInChI = 1S/C12H12N2S/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2
⚫ | FlashPt = 234.9 °C
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| Autoignition = }}
| StdInChIKey = ICNFHJVPAJKPHW-UHFFFAOYSA-N }}
⚫ |Section2={{Chembox Properties
⚫ | Formula = C<sub>12</sub>H<sub>12</sub>N<sub>2</sub>S
⚫ | MolarMass = 216.3 g/mol
⚫ | Appearance = Brown-brown violet powder or needles
⚫ | Density =1.26 g/cm<sup>3</sup>
| MeltingPtC = 105 to 107
| MeltingPt_notes =
| BoilingPtC = 464.8
| BoilingPt_notes = @ 760mmHg
| Solubility = }}
⚫ |Section3={{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPtC = 234.9
| AutoignitionPtC = }}
}} }}


'''4,4′-Thiodianiline''' (TDA) is the ] with the formula (H2NC6H4)2S. It is classified as a ] and a ]. It typically appears as an (off-)white solid powder. An ] of TDA is the drug ], for which the sulphur species is oxidised.
'''4,4'-Thiodianiline''' (TDA) is an ] which is presumed to be ]ic to humans.

== Chemical structure and properties ==
TDA is not combustible, but when heated it may decompose to form irritating and toxic fumes. An analogue of TDA is ].


== Synthesis == == Synthesis ==
] is boiled in excess ] over several hours to produce three isomers (1,1′; 1,4; 4,4′) of TDA.<ref name=Hodgson>{{cite journal |last=Hodgson |first=Herbert Henry|date= January 1924|title=Direct sulphuration of aniline |url=https://pubs.rsc.org/is/content/articlelanding/1924/ct/ct9242501855 |journal=J. Chem. Soc., Trans. |volume=1924 |issue=125 |pages=1855–1858|doi=10.1039/CT9242501855 |access-date=11 February 2016}}</ref> 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<ref>{{cite journal|last1=Nietzki|first1=R|last2=Bothof|first2=Heinrich|title=The Understanding of Thioanilines|journal=Reports of the German Chemical Society|volume=27|issue=3|pages=3261–3263|year=1894|doi=10.1002/cber.189402703119|url=https://zenodo.org/record/1425762}}</ref> shows indications that including an oxide of lead may maximize the yield of the 4,4′ variant that this page refers to.
] is reacted with ] to produce TDA.


== Uses == == Uses ==
TDA was used as a chemical intermediate in the production of three dyes: ], ] and ], as well as the medicine ]. TDA has also been used in the synthesis of polyimine ].<ref>{{Cite journal| last = Schoustra| first = Sybren K.| author2 = Dijksman, Joshua A.| author3= Zuilhof, Han| author4 = Smulders, Maarten M. J.| title = Molecular control over vitrimer-like mechanics – tuneable dynamic motifs based on the Hammett equation in polyimine materials | journal = Chemical Science |year=2021 | volume = 12 | issue = 1| pages = 293–302 | doi = 10.1039/d0sc05458e |issn=2041-6520 | pmid = 34163597| pmc = 8178953}}</ref>
TDA was used almost exclusively as a chemical intermediate in the production of three dyes: ], ] and ].


==Production== ==Production==
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==Toxicity== ==Toxicity==
TDA has caused mutations in some strains of '']'' and has caused tumors in laboratory mice and rats. TDA has caused mutations in some strains of '']'' and has caused tumors in laboratory mice and rats.

==Related compounds==
* ]
* ]
* ]


== References == == References ==
<references/>
{{No footnotes|date=February 2011}}
* lookchem{{Clarify|date=February 2011}}
* http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s173thio.pdf

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{{Organic-chem-stub}}


⚫ {{DEFAULTSORT:Thiodianiline, 4, 4-}}
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