Xanthene: Difference between revisions

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			{{Short description\|Chemical compound used to make dyes}}
	{{Distinguish\|xanthine}}		{{Distinguish\|xanthine}}
	{{Unreferenced\|date=December 2009}}
	{{Chembox		{{Chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~406257091~~
			\| Watchedfields = changed
		⚫	\| verifiedrevid = 412200450
	\| ImageFile = Xanthen.svg		\| ImageFile = Xanthen.svg
	\| ImageSize = ~~200px~~		\| ImageSize =
			\| ImageAlt = Skeletal formula
	\| IUPACName = ''9H''-Xanthene
			\| ImageFile1 = Xanthene-3D-balls.png
⚫	\| OtherNames = Dibenzopyran<br>10''H''-9-~~oxaanthracene~~
			\| ImageSize1 = 220
⚫	\| Section1 = {{Chembox Identifiers
			\| ImageAlt1 = Ball-and-stick model
			\| PIN = 9''H''-Xanthene<ref>{{cite book \|author=] \|date=2014 \|title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 \|publisher=] \|pages=213 \|doi=10.1039/9781849733069 \|isbn=978-0-85404-182-4}}</ref>
		⚫	\| OtherNames = Dibenzopyran<br>10''H''-9-Oxaanthracene
		⚫	\|Section1={{Chembox Identifiers
	\| Abbreviations =		\| Abbreviations =
	\| CASNo = 92-83-1		\| CASNo = 92-83-1
	\| CASNo_Ref = {{cascite}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
			\| Beilstein = 133939
			\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
			\| ChEBI = 10057
			\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
			\| ChEMBL = 486760
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\| ChemSpiderID = 6840
	\| EINECS = 202-194-4		\| EINECS = 202-194-4
	\| ~~PubChem~~ =		\| Gmelin = 83576
			\| KEGG_Ref = {{keggcite\|changed\|kegg}}
	\| SMILES = c1(Oc2ccccc2C3)c3cccc1
	\| ~~InChI~~ =		\| KEGG = C01464
	\| ~~RTECS~~ =		\| PubChem = 7107
	\| ~~MeSHName~~ =		\| RTECS =
	\| ~~ChEBI~~ =		\| MeSHName =
	\| ~~KEGG_Ref~~ = {{~~keggcite~~\|correct\|~~kegg~~}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| ~~KEGG~~ =		\| UNII = A762Z8101Y
			\| InChI = 1/C13H10O/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2
	\| ATCCode_prefix =
			\| InChIKey = GJCOSYZMQJWQCA-UHFFFAOYAO
	\| ATCCode_suffix =
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
⚫	\| ATC_Supplemental =}}
			\| StdInChI = 1S/C13H10O/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2
⚫	\| Section2 = {{Chembox Properties
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
	\| Formula = {{Carbon}}<sub>13</sub>{{Hydrogen}}<sub>10</sub>{{Oxygen}}
			\| StdInChIKey = GJCOSYZMQJWQCA-UHFFFAOYSA-N
	\| MolarMass = 182.22 g/mol
			\| SMILES = O1c2ccccc2Cc3ccccc31
			}}
		⚫	\|Section2={{Chembox Properties
			\| C=13 \| H=10 \| O=1
	\| Appearance = Yellow solid		\| Appearance = Yellow solid
	\| Density =		\| Density =
	\| ~~MeltingPt~~ = 101~~-102~~ °C		\| MeltingPtC = 101 to 102
			\| MeltingPt_ref = <ref name=Aldrich> at ]</ref>
	\| Melting_notes =
	\| ~~BoilingPt~~ = 310~~-312~~ °C		\| BoilingPtC = 310 to 312
			\| BoilingPt_ref = <ref name=Aldrich/>
	\| Boiling_notes =
	\| Solubility =		\| Solubility =
	\| SolubleOther =		\| SolubleOther =
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	\| pKa =		\| pKa =
	\| pKb = }}		\| pKb = }}
	\| ~~Section7~~ = {{Chembox ~~Hazards~~		\|Section6={{Chembox Pharmacology
	\| ~~EUClass~~ =		\| ATCCode_prefix =
	\| ~~EUIndex~~ =		\| ATCCode_suffix =
		⚫	\| ATC_Supplemental =
			}}
			\|Section7={{Chembox Hazards
	\| MainHazards =		\| MainHazards =
	\| NFPA-H =		\| NFPA-H =
	\| NFPA-F =		\| NFPA-F =
	\| NFPA-R =		\| NFPA-R =
	\| NFPA-O =		\| NFPA-S =
			\| Hazards_ref=<ref>{{cite web \|title=Xanthene 99% \|url=https://www.sigmaaldrich.com/AU/en/product/aldrich/x201 \|publisher=Sigma Aldrich}}</ref>
	\| RPhrases = {{R42}} {{R43}}
			\| GHSPictograms = {{GHS07}}
	\| SPhrases = {{S22}} {{S36}} {{S37}} {{S45}}
			\| GHSSignalWord = Warning
	\| RSPhrases =
			\| HPhrases = {{H-phrases\|317}}
			\| PPhrases = {{P-phrases\|280}}
	\| FlashPt =		\| FlashPt =
	\| ~~Autoignition~~ =		\| AutoignitionPt =
	\| ExploLimits =		\| ExploLimits =
	\| PEL = }}		\| PEL =
			}}
	}}		}}
			'''Xanthene''' (9''H''-xanthene, 10''H''-9-oxaanthracene) is the ] with the formula CH<sub>2</sub><sub>2</sub>O. 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.<ref name=Ull>{{Ullmann's \| last1 = Gessner \| first1 = Thomas \| last2 = Mayer \| first2 = Udo \| title = Triarylmethane and Diarylmethane Dyes \| year = 2000 \| doi = 10.1002/14356007.a27_179}}</ref>

			==Xanthene dyes==
	'''Xanthene''' (9''H''-xanthene, 10''H''-9-oxaanthracene) is a yellow ] ]. Its chemical formula is {{Carbon}}<sub>13</sub>{{Hydrogen}}<sub>10</sub>{{Oxygen}}. It is soluble in ]. Its melting point is 101-102 °C and its boiling point is 310-312 °C. Xanthene is used as a ] and it is also a useful intermediate in ].
			]s are commercial dyes with xanthene cores.]]
		⚫	]s that contain a xanthene core include ], ], ]s, and ]s. Xanthene dyes tend to be ], yellow to pink to bluish red, brilliant dyes. Many xanthene dyes can be prepared by condensation of derivates of ] with derivates of ] or ].
			{{Break\|5}}

			==Further reading==
⚫	~~Derivatives~~ of ~~xanthene~~ ~~are~~ ~~commonly~~ ~~referred~~ ~~to collectively as xanthenes, and among other uses are the basis of a class of~~ ]~~s which includes~~ ], ]s, and ]s. Xanthene dyes tend to be ], yellow to pink to bluish red, brilliant dyes. Many xanthene dyes can be prepared by condensation of derivates of ] with derivates of ] or ].
			*{{cite book\|chapter=Photochemistry of the Xanthene Dyes\|author1=Neckers, Douglas C. \|author2=Valdes-Aguilera Oscar M. \|title=Advances in Photochemistry\|series=<!--Advances in Photochemistry-->\|year=1993\|volume=18\|pages=315–94\|doi=10.1002/9780470133491.ch4\|isbn=9780470133491}}

	==See also==		==See also==
	* ]		* ]
	* Xanthene
	* ]		* ]

			==References==
			{{Reflist}}

			]
	]		]
	]		]


	{{Organic-compound-stub}}

	]
	]
	]
	]
	]
	]

Latest revision as of 02:54, 29 November 2024

Chemical compound used to make dyes Not to be confused with xanthine.

Xanthene
Names


Preferred IUPAC name 9H-Xanthene
Other names Dibenzopyran 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,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
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

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.
^ 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.

Categories:

Latest revision as of 02:54, 29 November 2024

Xanthene dyes

Further reading

See also

References