Xanthene

Xanthene
Names
	Preferred IUPAC name 9H-Xanthene
	Other names Dibenzo[a,e]pyran; 10H-9-Oxaanthracene
Identifiers
CAS Number	92-83-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	133939
ChEBI	CHEBI:10057 ;
ChEMBL	ChEMBL486760 ;
ChemSpider	6840 ;
ECHA InfoCard	100.001.996
EC Number	202-194-4;
Gmelin Reference	83576
KEGG	C01464 ;
PubChem CID	7107;
UNII	A762Z8101Y ;
CompTox Dashboard (EPA)	DTXSID1059070 ;
	InChI InChI=1S/C13H10O/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2 Key: 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,9H2 Key: GJCOSYZMQJWQCA-UHFFFAOYAO;
	SMILES O1c2ccccc2Cc3ccccc31;
Properties
Chemical formula	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)
Boiling point	310 to 312 °C (590 to 594 °F; 583 to 585 K)
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

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.

References

^ 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.
^ ^a ^b Xanthene at Sigma-Aldrich
^ "Xanthene 99%". Sigma Aldrich.
^ 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.

[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.

[Aldrich-2] Xanthene at Sigma-Aldrich

[3] "Xanthene 99%". Sigma Aldrich.

[Ull-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.

[4]

[1]

[2]

[3]

Xanthene

Contents

Xanthene dyes

Further reading

See also

References

Names


Preferred IUPAC name 9H-Xanthene^[1]
Other names Dibenzo[a,e]pyran 10H-9-Oxaanthracene
Identifiers
CAS Number	92-83-1^Y
3D model (JSmol)	Interactive image
Beilstein Reference	133939
ChEBI	CHEBI:10057^Y
ChEMBL	ChEMBL486760^Y
ChemSpider	6840^Y
ECHA InfoCard	100.001.996
EC Number	202-194-4
Gmelin Reference	83576
KEGG	C01464^N
PubChem CID	7107
UNII	A762Z8101Y^Y
CompTox Dashboard (EPA)	DTXSID1059070
InChI 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
SMILES O1c2ccccc2Cc3ccccc31
Properties
Chemical formula	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:
Pictograms
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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references