Thiocarbanilide

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.

Thiocarbanilide

Names
Preferred IUPAC name N,N'-Diphenylthiourea
Other names 1,3-Diphenylthiourea sym-Diphenylthiourea Diphenylthiourea 1,3-Diphenyl-2-thiourea DPTU Sulfocarbanilide
Identifiers
CAS Number	102-08-9
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL275260
ChemSpider	610932
ECHA InfoCard	100.002.732
PubChem CID	700999
UNII	9YCB5VR86Z
CompTox Dashboard (EPA)	DTXSID4026139
InChI InChI=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) Key: FCSHMCFRCYZTRQ-UHFFFAOYSA-N 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) Key: FCSHMCFRCYZTRQ-UHFFFAOYAC
SMILES S=C(Nc1ccccc1)Nc2ccccc2
Properties
Chemical formula	C13H12N2S
Molar mass	228.312 g/mol
Appearance	White powder
Density	1.32 g/cm^3
Melting point	154.5 °C (310.1 °F; 427.6 K)
Boiling point	decomposes
Solubility in water	slightly soluble in water
Solubility	very soluble in ethanol, diethyl ether, chloroform[1]
Hazards
NFPA 704 (fire diamond)	1 2 0
Flash point	164.7 °C (328.5 °F; 437.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Uses

Thiocarbanilide is commonly used as a vulcanization accelerator for rubber,[2] and as a stabilizer for PVC and PVDC. Its use as a vulcanization accelerator was discovered by BF Goodrich chemist George Oenslager.[3]

Reactions

Thiocarbanilide reacts with phosphorus pentachloride or hydrochloric acid, dilute sulfuric acid, acetic anhydride or iodine to produce phenyl isothiocyanate.

Toxicology

Oral, rat: LD₅₀ = 50 mg/kg.

References

1. Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–242, ISBN 0-8493-0594-2
2. 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
3. Trumbull, H. L. (1933). "Accomplishments of the Medalist". Ind. Eng. Chem. 25 (2): 230–232. doi:10.1021/ie50278a030.