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1,3-Diphenylurea

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1,3-Diphenylurea
Names
Preferred IUPAC name N,N′-Diphenylurea
Other names 1,3-Diphenylurea; Diphenylurea; carbanilide
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 782650
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.731 Edit this at Wikidata
EC Number
  • 203-003-7
Gmelin Reference 143821
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H12N2O/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: GWEHVDNNLFDJLR-UHFFFAOYSA-N
SMILES
  • c1ccc(cc1)N/C(=N\c2ccccc2)/O
Properties
Chemical formula C13H12N2O
Molar mass 212.252 g·mol
Melting point 239–241 °C (462–466 °F; 512–514 K)
Boiling point 262 °C (504 °F; 535 K)
Magnetic susceptibility (χ) -127.5·10 cm/mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H312, H332
Precautionary statements P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

1,3-Diphenylurea is a phenylurea-type compound with the formula (PhNH)2CO (Ph = C6H5). It is a colorless solid that is prepared by transamidation of urea with aniline.

DPU is a cytokinin, a type of plant hormone that induces flower development. The cytokinin effect of DPU is relatively low, but other more potent phenylurea-type cytokinins have been reported.

It was detected in coconut milk.

References

  1. Effect of cytokinin-active phenylurea derivatives on shoot multiplication. T. Genkov and I. Ivanova, Bulg. J. Plant Physiol., 1995, 21(1), pages 73–83 (link to article at researchgate)
  2. Shantz, E. M.; Steward, F. C. (1955). "The Identification of Compound A from Coconut Milk as 1,3-Diphenylurea". Journal of the American Chemical Society. 77 (23): 6351. doi:10.1021/ja01628a079.

External links


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