Pararosaniline: Difference between revisions

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Revision as of 12:32, 31 July 2011 editCheMoBot (talk \| contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref') per Chem/Drugbox validation (report [[Wik← Previous edit		Latest revision as of 04:16, 12 January 2025 edit undoPreimage (talk \| contribs)Extended confirmed users1,364 edits →Lede: leuco -> free base: although leuco technically applies (I think), too easy to confuse with the reduced leuco-form of triarylmethane dyes
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	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~433355521~~
			\| Watchedfields = changed
⚫	\| Name = Pararosaniline
		⚫	\| verifiedrevid = 444040939
⚫	\| ImageFile = Pararosaniline.png
		⚫	\| Name = Pararosaniline
⚫	\| IUPACName = -1-cyclohexa-2,5-dienylidene]~~azanium~~ ~~chloride~~
		⚫	\| ImageFile = Pararosaniline.png
⚫	\| OtherNames = Pararosaniline ~~hydrochloride~~</br>~~Pararosaniline chloride~~</br>C.I. 42500<~~/br>C.I. Basic Red 9, monohydrochloride</~~br>Para magenta
			\| ImageAlt = A resonance structure for pararosaniline hydrochloride
⚫	\| Section1 = {{Chembox Identifiers
		⚫	\| IUPACName = -1-cyclohexa-2,5-dienylidene]dianiline
⚫	\| ~~CASNo~~ = 569-61-9
		⚫	\| OtherNames = Pararosaniline<br>''p''-rosaniline<br>C.I. 42500<br>Para magenta
⚫	\| PubChem = ~~11292~~
		⚫	\|Section1={{Chembox Identifiers
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
			\| CASNo = 479-73-2
			\| CASNo1_Ref = {{cascite\|correct\|CAS}}
		⚫	\| CASNo1 = 569-61-9
			\| CASNo1_Comment =(])
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = C19210		\| KEGG = C19210
			\| ChEBI_Ref = {{ebicite\|changed\|EBI}}
	\| SMILES = C1=CC(=)C=CC1=C(C2=CC=C(C=C2)N)C3=CC=C(C=C3)N.
			\| ChEBI = 87663
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = 20N4C0M8NM
			\| UNII1_Ref = {{fdacite\|correct\|FDA}}
			\| UNII1 = 444C2M8JKN
			\| UNII1_Comment = (])

		⚫	\| PubChem = 11293
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
			\| ChemSpiderID = 10819
			\| SMILES = c1cc(ccc1C(=C2C=CC(=N)C=C2)c3ccc(cc3)N)N
			\| InChI = 1/C19H17N3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20H,21-22H2
			\| InChIKey = AFAIELJLZYUNPW-UHFFFAOYAS
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 1S/C19H17N3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20H,21-22H2
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = AFAIELJLZYUNPW-UHFFFAOYSA-N

	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
	\| Formula = C<sub>19</sub>H<sub>18</sub>~~ClN~~<sub>3</sub>		\| Formula = C<sub>19</sub>H<sub>17</sub>N<sub>3</sub>
	\| MolarMass = 323.82 g/mol		\| MolarMass = {{ubl\|287.36 g/mol\|323.83 g/mol (HCl)}}
	\| Appearance = Green crystalline solid		\| Appearance = Green crystalline solid
	\| Density =		\| Density =
	\| Solubility = Slightly soluble		\| Solubility = Slightly soluble
	\| ~~MeltingPt~~ = 268~~-270°C~~ ~~(541-543~~ ~~K) dec.~~		\| MeltingPtC = 268 to 270
			\| MeltingPt_notes = decomposes
	\| BoilingPt =
	\| ~~pKa~~ =		\| BoilingPt =
			\| pKa =
	}}		}}
	\| Section3 = {{Chembox Structure		\|Section3={{Chembox Structure
	\| CrystalStruct =		\| CrystalStruct =
	\| Dipole =		\| Dipole =
	}}		}}
	\| Section7 = {{Chembox Hazards		\|Section7={{Chembox Hazards
	\| ~~ExternalMSDS~~ =		\| ExternalSDS =
	\| MainHazards =		\| MainHazards =
⚫	}}
⚫	\| Section8 = {{Chembox Related
⚫	\| OtherAnions =
	\| Function =
	\| OtherFunctn =
	\| OtherCpds =
	}}		}}
		⚫	\|Section8={{Chembox Related
		⚫	\| OtherAnions =
			\| OtherFunction_label =
			\| OtherFunction =
			\| OtherCompounds =
		⚫	}}
	}}		}}

			'''Pararosaniline''', '''pararosaniline free base''', '''Basic Red 9''', or '''] 42500''' is an ] with the ] {{chem2\|(H2NC6H4)2C\d(C6H4NH)}}.<ref name=ChebiFreeBase>{{Cite web \|title=pararosaniline free base (CHEBI:75372) \|work=] \|access-date=11 January 2025 \|url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:75372}}</ref> It is the ] form of '''pararosaniline hydrochloride''', {{chem2\|+Cl-}}, a ] solid with a variety of uses as a ].<ref>Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in '']'' 2002, ], Weinheim.{{doi\|10.1002/14356007.a27_179}}</ref><ref name=ChEBIHydrochloride>{{Cite web \|title=pararosaniline (CHEBI:87663) \|work=] \|access-date=11 January 2025 \|url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:87663}}</ref> It is one of the four components of ].<ref>Horobin RW, Kiernan JA (2002) ''Conn's Biological Stains'', 10th ed. Oxford: BIOS.</ref> It is structurally related to other triarylmethane dyes called ]s (e.g. ]) which feature methyl groups on nitrogen.
	'''Pararosaniline''', '''Basic Red 9''', or '''] 42500''' is a ] ] having ] {{carbon}}<sub>19</sub>{{hydrogen}}<sub>18</sub>{{nitrogen}}<sub>3</sub>{{chlorine}}. It is one of the four components of basic ]. (The others are rosaniline, ] and magenta II.)<ref>Horobin RW, Kiernan JA (2002) Conn's Biological Stains, 10th ed. Oxford: BIOS.</ref> Pararosaniline, which is sold as a single dye, may make the best ]. It is the only basic fuchsine component suitable for making the aldehyde-fuchsine stain for pancreatic islet beta cells<ref>Mowry RW, Emmel VM (1978) Aldehyde fuchsin staining, direct or after oxidation: problems and remedies, with special reference to pancreatic B cells, pituitaries and elastic fibers. Stain Technology 53: 141-154.</ref>

			It is prepared by the condensation of ] and {{ill\|4-Aminobenzaldehyde\|lt=''p''-aminobenzaldehyde\|pt\|4-Aminobenzaldeído}}. Alternatively, it arises from the oxidation of ] in the presence of aniline.

			==Uses==
			*It is used to dye ] fibers.
			*It is used to detect ].<ref>{{cite journal\|journal=Analytical Chemistry\|volume=34\|issue=12\|issn=0003-2700\|date=1962\|pages=1660–1662\|doi=10.1021/ac60192a001\|url=https://pubs.acs.org/doi/abs/10.1021/ac60192a001\|title=Effect of Pararosaniline in the Trace Determination of Sulfur Dioxide.\|accessdate=2023-03-03\|author=J. B. Pate, J. P. Lodge, A. F. Wartburg}}</ref>
			*Pararosaniline is used as a colorimetric test for aldehydes, in the ]. It is the only basic fuchsine component suitable for making the aldehyde-fuchsine stain for pancreatic islet beta cells.<ref>{{cite journal \| last1 = Mowry \| first1 = RW \| last2 = Emmel \| first2 = VM \| year = 1978 \| title = Aldehyde fuchsin staining, direct or after oxidation: problems and remedies, with special reference to pancreatic B cells, pituitaries and elastic fibers \| journal = Stain Technology \| volume = 53 \| issue = 3 \| pages = 141–154 \| doi=10.3109/10520297809111457\| pmid = 83035 }}</ref>
			*It has use as an ]. <ref>{{Cite patent\|country=GB\|number=908634\|title=Pharmaceutical compositions containing pararosaniline or derivatives thereof\|pubdate=1962-10-24\|assign=]}}</ref>

			==Related compounds==
			* ]
			* ]
			* ]
			* ]

	==References==		==References==
	{{reflist}}		{{reflist}}

	==Further reading==		==Further reading==
	*{{citation\| year=1971 \| title= Colour Index 3rd Edition Volume 4 \| pages=4388 \| publisher=Society of Dyers and Colourists \| place=Bradford \| url=http://www.colour-index.org/help/3121_Triarylmethane.pdf }}.		*{{citation \| year=1971 \| title=Colour Index 3rd Edition Volume 4 \| pages=4388 \| publisher=Society of Dyers and Colourists \| place=Bradford \| url=http://www.colour-index.org/help/3121_Triarylmethane.pdf \| archive-url=https://web.archive.org/web/20110719160728/http://www.colour-index.org/help/3121_Triarylmethane.pdf \| url-status=dead \| archive-date=2011-07-19 }}.
	*{{citation \| last1=Gessner \| first1=T. \| last2=Mayer \| first2=U. \| year=2002 \| contribution= Triarylmethane and Diarylmethane Dyes \| title= Ullmann's Encyclopedia of Industrial Chemistry 6th Edition \| publisher=Wiley-VCH \| place=Weinheim \| doi=10.1002/14356007.a27_179 }}.		*{{citation \| last1=Gessner \| first1=T. \| last2=Mayer \| first2=U. \| year=2002 \| contribution= Triarylmethane and Diarylmethane Dyes \| title= Ullmann's Encyclopedia of Industrial Chemistry 6th Edition \| publisher=Wiley-VCH \| place=Weinheim \| doi=10.1002/14356007.a27_179 }}.

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	{{organic-compound-stub}}

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Latest revision as of 04:16, 12 January 2025

Pararosaniline
Names

IUPAC name -1-cyclohexa-2,5-dienylidene]dianiline
Other names Pararosaniline p-rosaniline C.I. 42500 Para magenta
Identifiers
CAS Number	479-73-2 569-61-9 (HCl)
3D model (JSmol)	Interactive image
ChEBI	CHEBI:87663
ChemSpider	10819
ECHA InfoCard	100.106.992
KEGG	C19210
PubChem CID	11293
UNII	20N4C0M8NM 444C2M8JKN (HCl)
CompTox Dashboard (EPA)	DTXSID5043845
InChI InChI=1S/C19H17N3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20H,21-22H2Key: AFAIELJLZYUNPW-UHFFFAOYSA-N InChI=1/C19H17N3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20H,21-22H2Key: AFAIELJLZYUNPW-UHFFFAOYAS
SMILES c1cc(ccc1C(=C2C=CC(=N)C=C2)c3ccc(cc3)N)N
Properties
Chemical formula	C₁₉H₁₇N₃
Molar mass	287.36 g/mol 323.83 g/mol (HCl)
Appearance	Green crystalline solid
Melting point	268 to 270 °C (514 to 518 °F; 541 to 543 K) decomposes
Solubility in water	Slightly soluble
Hazards
Safety data sheet (SDS)	External MSDS
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

Pararosaniline, pararosaniline free base, Basic Red 9, or C.I. 42500 is an organic compound with the formula (H₂NC₆H₄)₂C=(C₆H₄NH). It is the free base form of pararosaniline hydrochloride, [(H₂NC₆H₄)₃C]Cl, a magenta solid with a variety of uses as a dye. It is one of the four components of basic fuchsine. It is structurally related to other triarylmethane dyes called methyl violets (e.g. crystal violet) which feature methyl groups on nitrogen.

It is prepared by the condensation of aniline and p-aminobenzaldehyde [pt]. Alternatively, it arises from the oxidation of 4,4'-bis(aminophenyl)methane in the presence of aniline.

Uses

It is used to dye polyacrylonitrile fibers.
It is used to detect sulfur dioxide.
Pararosaniline is used as a colorimetric test for aldehydes, in the Schiff test. It is the only basic fuchsine component suitable for making the aldehyde-fuchsine stain for pancreatic islet beta cells.
It has use as an antischistosomal.

Related compounds

References

"pararosaniline free base (CHEBI:75372)". ChEBI. Retrieved 11 January 2025.
Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a27_179
"pararosaniline (CHEBI:87663)". ChEBI. Retrieved 11 January 2025.
Horobin RW, Kiernan JA (2002) Conn's Biological Stains, 10th ed. Oxford: BIOS.
J. B. Pate, J. P. Lodge, A. F. Wartburg (1962). "Effect of Pararosaniline in the Trace Determination of Sulfur Dioxide". Analytical Chemistry. 34 (12): 1660–1662. doi:10.1021/ac60192a001. ISSN 0003-2700. Retrieved 2023-03-03.{{cite journal}}: CS1 maint: multiple names: authors list (link)
Mowry, RW; Emmel, VM (1978). "Aldehyde fuchsin staining, direct or after oxidation: problems and remedies, with special reference to pancreatic B cells, pituitaries and elastic fibers". Stain Technology. 53 (3): 141–154. doi:10.3109/10520297809111457. PMID 83035.
GB 908634, "Pharmaceutical compositions containing pararosaniline or derivatives thereof", published 1962-10-24, assigned to Parke, Davis & Co.

Latest revision as of 04:16, 12 January 2025

Uses

Related compounds

References

Further reading