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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 433355521 |
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| Watchedfields = changed |
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| Name = Pararosaniline |
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| verifiedrevid = 444040939 |
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| ImageFile = Pararosaniline.png |
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| Name = Pararosaniline |
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| IUPACName = -1-cyclohexa-2,5-dienylidene]azanium chloride |
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| ImageFile = Pararosaniline.png |
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| OtherNames = Pararosaniline hydrochloride</br>Pararosaniline chloride</br>C.I. 42500</br>C.I. Basic Red 9, monohydrochloride</br>Para magenta |
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| IUPACName = -1-cyclohexa-2,5-dienylidene]dianiline |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Pararosaniline<br>''p''-rosaniline<br>C.I. 42500<br>Para magenta |
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| CASNo = 569-61-9 |
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|Section1={{Chembox Identifiers |
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| PubChem = 11292 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 479-73-2 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 569-61-9 |
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| CASNo1_Comment =(]) |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C19210 |
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| KEGG = C19210 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| UNII = 20N4C0M8NM |
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| ChEBI = 87663 |
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| SMILES = C1=CC(=)C=CC1=C(C2=CC=C(C=C2)N)C3=CC=C(C=C3)N. |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 20N4C0M8NM |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = 444C2M8JKN |
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| UNII1_Comment = (]) |
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| PubChem = 11293 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 10819 |
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| SMILES = c1cc(ccc1C(=C2C=CC(=N)C=C2)c3ccc(cc3)N)N |
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| 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 |
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| InChIKey = AFAIELJLZYUNPW-UHFFFAOYAS |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = AFAIELJLZYUNPW-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>19</sub>H<sub>18</sub>ClN<sub>3</sub> |
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| Formula = C<sub>19</sub>H<sub>17</sub>N<sub>3</sub> |
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| MolarMass = 323.82 g/mol |
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| MolarMass = 323.83 g/mol |
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| Appearance = Green crystalline solid |
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| Appearance = Green crystalline solid |
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| Density = |
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| Density = |
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| Solubility = Slightly soluble |
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| Solubility = Slightly soluble |
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| MeltingPt = 268-270°C (541-543 K) dec. |
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| MeltingPtC = 268 to 270 |
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| MeltingPt_notes = decomposes |
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| Section3 = {{Chembox Structure |
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| CrystalStruct = |
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| Dipole = |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| Section8 = {{Chembox Related |
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| Function = |
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|Section8={{Chembox Related |
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'''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> |
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'''Pararosaniline''', '''Basic Red 9''', or '''] 42500''' is an ] with the ] Cl. It is 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> It is one of the four components of basic ]. (The others are ], ] and magenta II.)<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 including ], which feature methyl groups on nitrogen. |
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It is prepared by the condensation of ] and para-aminobenzaldehyde. Alternatively, it arises from the oxidation of 4,4'-bis(aminophenyl)methane in the presence of aniline. |
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==Uses== |
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*It is used to dye ] fibers. |
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*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> |
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*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> |
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*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> |
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==Related compounds== |
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* ] |
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* ] |
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* ] |
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* ] |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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==Further reading== |
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==Further reading== |
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*{{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 }}. |
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*{{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 }}. |
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*{{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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*{{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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