4,4'-THIODIANILINE

4,4'-THIODIANILINE Basic information
Product Name:4,4'-THIODIANILINE
Synonyms:4,4-diaminodiphenylsulphide;4,4'-Thioaniline;4,4'-Thiobis(aniline);4,4'-Thiobisbenzenamine;4-[(4-Aminophenyl)sulfanyl]phenylamine;Aniline, 4,4'-thiodi-;Bis(4-aminophenyl)sulphide;Bis(p-aminophenyl)sulphide
CAS:139-65-1
MF:C12H12N2S
MW:216.3
EINECS:205-370-9
Product Categories:Diphenyl Sulfides (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Amines
Mol File:139-65-1.mol
4,4'-THIODIANILINE Structure
4,4'-THIODIANILINE Chemical Properties
Melting point 105-107 °C(lit.)
Boiling point 361 °C
density 1.1391 (rough estimate)
refractive index 1.5700 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility DMSO (Slightly), Methanol (Slightly)
form neat
pka4.55±0.10(Predicted)
color Pale Brown
BRN 1875513
InChIKeyICNFHJVPAJKPHW-UHFFFAOYSA-N
CAS DataBase Reference139-65-1(CAS DataBase Reference)
NIST Chemistry ReferenceBenzenamine, 4,4'-thiobis-(139-65-1)
IARC2B (Vol. 27, Sup 7) 1987
EPA Substance Registry System4,4'-Thiodianiline (139-65-1)
Safety Information
Hazard Codes T,N
Risk Statements 45-22-51/53
Safety Statements 53-45-61
RIDADR UN 3077 9/PG 3
WGK Germany 3
RTECS BY9625000
8-10-21
HazardClass IRRITANT
PackingGroup III
HS Code 29309090
Hazardous Substances Data139-65-1(Hazardous Substances Data)
Toxicitymouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01564,
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
4,4'-THIODIANILINE Usage And Synthesis
Chemical PropertiesA brown-purple powder or needles.
Uses4,4'-Thiodianiline is a carcinogenic aromatic amine used in the textile industry. It can also be used to modify electrodes in solar cells. Dyes and metabolites, Environmental Testing.
Uses4,4′-Diaminodiphenyl sulfide may be employed for the fabrication of quantum wires and quantum dots by chemical vapor deposition.
It may be used for the preparation of the following:
  • polypyromellitimides
  • sulfur-containing copolyimides
  • polyamides
Uses4,4′-Thiodianiline was used almost exclusively as a chemical intermediate in the production of three dyes: C.I. mordant yellow 16, milling red G, and milling red FR. However, only mordant yellow 16 had any commercial significance in the United States (IARC 1982, HSDB 2009); it was used to dye wool and for printing on wool, silk, and cotton (SDC 1971). Mordant yellow 16 has been used as an indicator in the U.S. government’s nerve gas detector program (SOCMA 2002). However, no uses of either 4,4′-thiodianiline or mordant yellow 16 since the early 1990s have been reported.
DefinitionChEBI: 4,4'-Thiodianiline is a substituted aniline.
General Description4,4'-Thiodianiline is a substituted aniline. It is a brown to violet colored solid aromatic amine that emits toxic fumes of nitrogen oxides, carbon monoxide, carbon dioxide, nitrogen and sulfur oxides when heated to decomposition. 4,4'-Thiodianiline is primarily used as a chemical intermediate in the production of certain dyes. 
Air & Water ReactionsInsoluble in water.
Reactivity Profile4,4'-THIODIANILINE is incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. May generate heat with these materials and hydrogen gas or hydrogen sulfide gas. May liberate hydrogen sulfide if heated to decomposition or mixed with an acid. Also incompatible with peroxides, phenols (acidic), epoxides, anhydrides, and acid halides.
Health HazardACUTE/CHRONIC HAZARDS: When heated to decomposition 4,4'-THIODIANILINE emits very toxic fumes.
Fire HazardFlash point data for 4,4'-THIODIANILINE are not available, however 4,4'-THIODIANILINE is probably combustible.
Safety ProfileConfirmed carcinogen with experimental carcinogenic and tumorigenic data. Poison by intravenous route. Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also SULFIDES.
Potential Exposure4,40-Thiodianiline is used as a dye intermediate; in organic sythesis; as a lab reagent. Antiplatyhelmintic agents; Carcinogens
Carcinogenicity4,4′-Thiodianiline is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
ShippingUN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9Miscellaneous hazardous material, Technical Name Required. UN3143 dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
Purification MethodsThe free base is used for the detection of NO3 ions. The diacetate crystallises from aqueous AcOH with m 182o and the sulfoxide, m 184o, forms prisms from EtOH or H2O. [Fuson & Melamed J Org Chem 13 690 I1948, Beilstein 1 3 III 1246, 13, IV 1246.]
IncompatibilitiesThis material may be combustible. 4,40-Thiodianiline is incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. May generate heat with these materials and hydrogen gas or hydrogen sulfide gas. May liberate hydrogen sulfide if heated to decomposition or mixed with an acid. Also incompatible with peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Light and moisture sensitive
Waste DisposalIt is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
BIS(4-HYDROXY-3-METHYLPHENYL) SULFIDE 4,4'-THIODIANILINE 2,2'-THIODIANILINE 4-NITRO-4'-AMINODIPHENYL SULFONE sulfoxone 4-ISOTHIOCYANATO-4'-NITRODIPHENYL SULFIDE SDDS BIS(4-NITROPHENYL) SULFIDE VITAS-BB TBB000179 ACID YELLOW 38 2,2'-THIOBIS(5-AMINOBENZENESULFONIC ACID) 4-AMINO-4'-NITRODIPHENYL SULFIDE ISOTHIOCYANATOPHENYL SULFONE solasulfone 4-ACETAMINO-4'-NITRODIPHENYL SULFONE 4,4-DIAMINO-2,2'-DICHLORODIPHENYL DISULFIDE 1-[(2,4-DINITROPHENYL)THIO]-2,4-DINITROBENZENE P-AZIDOPHENYL SULFONE

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