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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
⚫ | IUPACName = -1-cyclohexa-2,5-dienylidene]dianiline
⚫ | Section1 = {{Chembox Identifiers
⚫ | OtherNames = Pararosaniline<br>''p''-rosaniline<br>C.I. 42500<br>Para magenta
⚫ | CASNo = 569-61-9
⚫ |Section1={{Chembox Identifiers
⚫ | PubChem = 11292
| 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}}
⚫ | UNII = 20N4C0M8NM
| ChEBI = 87663
| SMILES = C1=CC(=)C=CC1=C(C2=CC=C(C=C2)N)C3=CC=C(C=C3)N.
| 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 = 323.83&nbsp;g/mol
| 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''', '''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> '''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.

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.

==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 22:41, 1 September 2024

Pararosaniline
Names
IUPAC name -1-cyclohexa-2,5-dienylidene]dianiline
Other names Pararosaniline
p-rosaniline
C.I. 42500
Para magenta
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.106.992 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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 323.83 g/mol
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, Basic Red 9, or C.I. 42500 is an organic compound with the formula Cl. It is a magenta solid with a variety of uses as a dye. It is one of the four components of basic fuchsine. (The others are rosaniline, new fuchsine and magenta II.) It is structurally related to other triarylmethane dyes called methyl violets including crystal violet, which feature methyl groups on nitrogen.

It is prepared by the condensation of aniline and para-aminobenzaldehyde. 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

  1. 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
  2. Horobin RW, Kiernan JA (2002) Conn's Biological Stains, 10th ed. Oxford: BIOS.
  3. 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)
  4. 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.
  5. GB 908634, "Pharmaceutical compositions containing pararosaniline or derivatives thereof", published 1962-10-24, assigned to Parke, Davis & Co. 

Further reading

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