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Thiocarbanilide

Summary

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
Thiocarbanilide
Names
Preferred IUPAC name
N,N′-Diphenylthiourea
Other names
1,3-Diphenylthiourea
sym-Diphenylthiourea
Diphenylthiourea
1,3-Diphenyl-2-thiourea
DPTU
Sulfocarbanilide
Identifiers
  • 102-08-9 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL275260 checkY
ChemSpider
  • 610932 checkY
ECHA InfoCard 100.002.732 Edit this at Wikidata
  • 700999
UNII
  • 9YCB5VR86Z checkY
  • DTXSID4026139 Edit this at Wikidata
  • 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) checkY
    Key: FCSHMCFRCYZTRQ-UHFFFAOYSA-N checkY
  • 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
  • S=C(Nc1ccccc1)Nc2ccccc2
Properties
C13H12N2S
Molar mass 228.312 g/mol
Appearance White powder
Density 1.32 g/cm3
Melting point 154.5 °C (310.1 °F; 427.6 K)
Boiling point decomposes
slightly soluble in water
Solubility very soluble in ethanol, diethyl ether, chloroform[1]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
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).
checkY verify (what is checkY☒N ?)
Infobox references

Uses edit

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 edit

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

Toxicology edit

Oral, rat: LD50 = 50 mg/kg.

References edit

  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.