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Xanthene

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(Redirected from Dibenzopyran) Chemical compound used to make dyes Not to be confused with xanthine.
Xanthene
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name 9H-Xanthene
Other names Dibenzopyran
10H-9-Oxaanthracene
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 133939
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.996 Edit this at Wikidata
EC Number
  • 202-194-4
Gmelin Reference 83576
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H10O/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2Key: GJCOSYZMQJWQCA-UHFFFAOYSA-N
  • InChI=1/C13H10O/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2Key: GJCOSYZMQJWQCA-UHFFFAOYAO
SMILES
  • O1c2ccccc2Cc3ccccc31
Properties
Chemical formula C13H10O
Molar mass 182.222 g·mol
Appearance Yellow solid
Melting point 101 to 102 °C (214 to 216 °F; 374 to 375 K)
Boiling point 310 to 312 °C (590 to 594 °F; 583 to 585 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H317
Precautionary statements P280
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Xanthene (9H-xanthene, 10H-9-oxaanthracene) is the organic compound with the formula CH22O. It is a yellow solid that is soluble in common organic solvents. Xanthene itself is an obscure compound, but many of its derivatives are useful dyes.

Xanthene dyes

Rhodamines are commercial dyes with xanthene cores.

Dyes that contain a xanthene core include bikaverin, fluorescein, eosins, and rhodamines. Xanthene dyes tend to be fluorescent, yellow to pink to bluish red, brilliant dyes. Many xanthene dyes can be prepared by condensation of derivates of phthalic anhydride with derivates of resorcinol or 3-aminophenol.




Further reading

See also

References

  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 213. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Xanthene at Sigma-Aldrich
  3. "Xanthene 99%". Sigma Aldrich.
  4. Gessner, Thomas; Mayer, Udo (2000). "Triarylmethane and Diarylmethane Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a27_179. ISBN 978-3527306732.
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