Thiocarbanilide
{{chembox
| Watchedfields = changed
| verifiedrevid = 470606959
| Name = Thiocarbanilide
| ImageFile = Thiocarbanilide.svg
| ImageSize =
| ImageName = Thiocarbanilide
| PIN = N,N′-Diphenylthiourea
| OtherNames=1,3-Diphenylthiourea
sym-Diphenylthiourea
Diphenylthiourea
1,3-Diphenyl-2-thiourea
DPTU
Sulfocarbanilide
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 610932
| PubChem = 700999
| InChI = 1/C13H12N2S/c16-13(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H,(H2,14,15,16)
| InChIKey = FCSHMCFRCYZTRQ-UHFFFAOYAC
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 275260
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H12N2S/c16-13(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H,(H2,14,15,16)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FCSHMCFRCYZTRQ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 102-08-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9YCB5VR86Z
| SMILES = S=C(Nc1ccccc1)Nc2ccccc2
}}
| Section2 = {{Chembox Properties
| Formula = C13H12N2S
| Appearance = White powder
| MolarMass = 228.312 g/mol
| Density = 1.32 g/cm3
| MeltingPtC = 154.5
| BoilingPt = decomposes
| Solubility = slightly soluble in water
| SolubleOther = very soluble in ethanol, diethyl ether, chloroform
{{Citation
| last = Lide
| first = David R.
| author-link =
| year = 1998
| title = Handbook of Chemistry and Physics
| edition = 87
| volume =
| series =
| publication-place = Boca Raton, Florida
| publisher = CRC Press
| id =
| isbn = 0-8493-0594-2
| doi =
| oclc =
| pages = 3–242
| url =
}}
}}
| Section7 = {{Chembox Hazards
| NFPA-H = 2
| NFPA-R = 0
| NFPA-F = 1
| FlashPtC = 164.7
}}
}}
Thiocarbanilide is an organic chemical compound with the formula (C6H5NH)2CS. This white solid is a derivative of thiourea. It is prepared by the reaction of aniline and carbon disulfide.
Uses
Thiocarbanilide is commonly used as a vulcanization accelerator for rubber,Hans-Wilhelm Engels, Herrmann-Josef Weidenhaupt, Manfred Pieroth, Werner Hofmann, Karl-Hans Menting, Thomas Mergenhagen, Ralf Schmoll, Stefan Uhrlandt "Rubber, 4. Chemicals and Additives" in Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a23_365.pub2}} and as a stabilizer for PVC and PVDC. Its use as a vulcanization accelerator was discovered by BF Goodrich chemist George Oenslager.{{cite journal | title = Accomplishments of the Medalist | first =H. L. | last = Trumbull| journal = Ind. Eng. Chem. | year = 1933| volume = 25| issue = 2| pages = 230–232 | doi = 10.1021/ie50278a030}}
Reactions
Thiocarbanilide reacts with phosphorus pentachloride, phosphorus pentoxide, acetic anhydride, and other reagent to produce phenyl isothiocyanate.{{OrgSynth |year=1926| author = F. B. Dains, R. Q. Brewster, and C. P. Olander | title = Phenyl isothiocyanate | volume = 6 | page = 72 | doi = 10.15227/orgsyn.006.0072}}
Toxicology
Oral, rat: {{LD50}} = 50 mg/kg.