Xanthene

Xanthene (9H-xanthene, 10H-9-oxaanthracene) is the organic compound with the formula CH2[C6H4]2O. 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.[4]

Not to be confused with xanthine.
Xanthene
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
9H-Xanthene[1]
Other names
Dibenzo[a,e]pyran
10H-9-Oxaanthracene
Identifiers
3D model (JSmol)
133939
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.996
EC Number
  • 202-194-4
83576
KEGG
UNII
  • InChI=1S/C13H10O/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2 ☒N
    Key: GJCOSYZMQJWQCA-UHFFFAOYSA-N ☒N
  • InChI=1/C13H10O/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2
    Key: GJCOSYZMQJWQCA-UHFFFAOYAO
  • O1c2ccccc2Cc3ccccc31
Properties
C13H10O
Molar mass 182.222 g·mol−1
Appearance Yellow solid
Melting point 101 to 102 °C (214 to 216 °F; 374 to 375 K)[2]
Boiling point 310 to 312 °C (590 to 594 °F; 583 to 585 K)[2]
Hazards[3]
GHS labelling:
GHS07: Exclamation mark
Warning
H317
P280
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

Xanthene dyes
Rhodamines are commercial dyes with xanthene cores.

Dyes that contain a xanthene core include 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
  • Neckers, Douglas C.; Valdes-Aguilera Oscar M. (1993). "Photochemistry of the Xanthene Dyes". Advances in Photochemistry. 18: 315–94. doi:10.1002/9780470133491.ch4. ISBN 9780470133491.

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.
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