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.

References

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Category:Thioureas

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