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{{Chembox
{{Chembox
| ImageFile = NewFuchsineStructure.png
| ImageFile = Neofuchsin.svg
| ImageSize =
| ImageSize =
| ImageAlt =
| ImageAlt =
| IUPACName =
| IUPACName =
| OtherNames = new fuchsin, Magenta III, Basic Violet 2, C.I. 42520
| OtherNames = New fuchsin; Magenta III; Basic Violet 2; C.I. 42520
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 3248-91-7
| CASNo = 3248-91-7
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
| PubChem =
| SMILES = }}
| ChEBI = 87671
⚫
| PubChem = 18611
⚫
| Section2 = {{Chembox Properties
| ChemSpiderID = 17578
| Formula = C<sub>22</sub>H<sub>24</sub>{{nitrogen}}<sub>3</sub>{{chlorine}}
| MolarMass =
| EC_number = 221-831-7
| UNII = A051F48W36
⚫
| Appearance = dark red solid
| Density =
| UNII_Comment = base
| MeltingPt =
| ChEMBL = 1979779
| StdInChI=1S/C22H23N3.ClH/c1-13-10-16(4-7-19(13)23)22(17-5-8-20(24)14(2)11-17)18-6-9-21(25)15(3)12-18;/h4-12,23H,24-25H2,1-3H3;1H
⚫
| BoilingPt =
| StdInChIKey = IPSIPYMEZZPCPY-UHFFFAOYSA-N
⚫
| Solubility = }}
| SMILES = CC1=CC(=C(C2=CC(=C(C=C2)N)C)C3=CC(=C(C=C3)N)C)C=CC1=[NH2+].[Cl-]
⚫
| Section3 = {{Chembox Hazards
}}
⚫
| MainHazards =
⚫
|Section2={{Chembox Properties
⚫
| FlashPt =
| C=22 | H=24 | N=3 | Cl=1
| Autoignition = }}
⚫
| Appearance = violet powder
| Density =
| MeltingPt =
⚫
| BoilingPt =
⚫
| Solubility = }}
⚫
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|315|318|319|335|350|351|373|410}}
| PPhrases = {{P-phrases|201|202|260|261|264|271|273|280|281|302+352|304+340|305+351+338|308+313|310|312|314|321|332+313|337+313|362|391|403+233|405|501}}
⚫
| MainHazards =
⚫
| FlashPt =
| AutoignitionPt = }}
}}
}}


'''New fuchsine''', (from [[German (language)|German]] "fuchs", ''fox'') is an organic compound]] with the [[chemical formula|formula]] [(CH3N(H)CH3C<sub>C</sub>H<sub>3</sub>)<sub>3</sub>C]Cl. It is a [[magenta (color)|magenta]]-colored solid that is used as a [[dye]]. It is one of the four components of basic [[fuchsine]], and one of the two that are available as single dyes.<ref>Horobin RW, Kiernan JA (2002) Conn's Biological Stains, 10th ed. Oxford: BIOS.</ref> The other is [[pararosaniline]].
'''New fuchsine''' is an organic compound with the [[chemical formula|formula]] [(H<sub>2</sub>N(CH<sub>3</sub>)C<sub>6</sub>H<sub>3</sub>)<sub>3</sub>C]Cl. It is a green-colored solid that is used as a [[dye]] of the [[triarylmethane dye|triarylmethane]] class. It is one of the four components of basic [[fuchsine]], and one of the two that are available as single dyes.<ref>Horobin RW, Kiernan JA (2002) Conn's Biological Stains, 10th ed. Oxford: BIOS.</ref> The other is [[pararosaniline]]. It is prepared by condensation of [[ortho-toluidine]] with formaldehyde. This process initially gives the [[benzhydrol]] [[4,4'-Bis(dimethylamino)benzhydrol|4,4'-bis(dimethylamino)benzhydrol]], which is further condensed to give the leuco (colorless) [[tertiary alcohol]] [(H<sub>2</sub>N(CH<sub>3</sub>)C<sub>6</sub>H<sub>3</sub>)<sub>3</sub>COH, which is oxidized in acid to give the dye.<ref>{{cite book|doi=10.1002/0471238961.2018091620080520.a01.pub2|chapter=Triphenylmethane and Related Dyes|title=Kirk-Othmer Encyclopedia of Chemical Technology|year=2013|last1=Thetford|first1=Dean|last2=Updated By Staff|isbn=978-0471238966}}</ref>

It is prepared by condensation of N-methyl[[toluidine]] with xylidene in the presence of [[hydrochloric acid]].


==Use as dye and stain==
==Use as dye and stain==
⚫
New fuchsine is used to dye [[polyacrylonitrile]], paper, and leather.{{cn|date=October 2019}} In biology, it can be used for [[staining (biology)|staining]] acid-fast organisms, e.g. by [[Ziehl–Neelsen stain]], and for making [[Schiff's reagent]]. As a primary amine, the dye can be diazotized in the laboratory, and the resulting diazonium salt used as a trapping agent in enzyme histochemistry.<ref>Lojda Z, Gossrau R, Schiebler TH (1979) Enzyme Histochemistry. A Laboratory Manual. Berlin: Springer-Verlag.</ref>
It is used to dye polyacrylonitrile, paper, and leather.<ref>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}}</ref>


==Etymology==
⚫
New fuchsine can be used for [[staining (biology)|staining]] acid fast organism, e.g. by [[Ziehl-Neelsen stain]], and for making Schiff's reagent. As a primary amine, the dye can be diazotized in the laboratory, and the resulting diazonium salt used as a trapping agent in enzyme histochemistry.<ref>Lojda Z, Gossrau R, Schiebler TH (1979) Enzyme Histochemistry. A Laboratory Manual. Berlin: Springer-Verlag.</ref>
The name fuchsine recognizes [[Leonhart Fuchs]].


== See also ==
== See also ==


* [[Fuchsine]]
* [[Fuchsine]]
* [[Pararosanilin]]
* [[Pararosaniline]]

⚫
==External links==
⚫
* [http://stainsfile.info/StainsFile/dyes/42520.htm New Fuchsin - '''StainsFile''']


==References==
==References==
<references/>
<references/>

⚫
==External links==
⚫
* [https://web.archive.org/web/20080128151521/http://stainsfile.info/StainsFile/dyes/42520.htm New Fuchsin - '''StainsFile''']


{{DEFAULTSORT:New Fuchsine}}
{{DEFAULTSORT:New Fuchsine}}
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[[Category:IARC Group 2B carcinogens]]
[[Category:IARC Group 2B carcinogens]]
[[Category:Anilines]]
[[Category:Anilines]]
[[Category:Carbocations]]


{{organic-compound-stub}}

Latest revision as of 22:40, 1 September 2024

New fuchsine
Names
Other names
New fuchsin; Magenta III; Basic Violet 2; C.I. 42520
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.019.847 Edit this at Wikidata
EC Number
  • 221-831-7
UNII
  • InChI=1S/C22H23N3.ClH/c1-13-10-16(4-7-19(13)23)22(17-5-8-20(24)14(2)11-17)18-6-9-21(25)15(3)12-18;/h4-12,23H,24-25H2,1-3H3;1H
    Key: IPSIPYMEZZPCPY-UHFFFAOYSA-N
  • CC1=CC(=C(C2=CC(=C(C=C2)N)C)C3=CC(=C(C=C3)N)C)C=CC1=[NH2+].[Cl-]
Properties
C22H24ClN3
Molar mass 365.91 g·mol−1
Appearance violet powder
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H315, H318, H319, H335, H350, H351, H373, H410
P201, P202, P260, P261, P264, P271, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

New fuchsine is an organic compound with the formula [(H2N(CH3)C6H3)3C]Cl. It is a green-colored solid that is used as a dye of the triarylmethane class. It is one of the four components of basic fuchsine, and one of the two that are available as single dyes.[1] The other is pararosaniline. It is prepared by condensation of ortho-toluidine with formaldehyde. This process initially gives the benzhydrol 4,4'-bis(dimethylamino)benzhydrol, which is further condensed to give the leuco (colorless) tertiary alcohol [(H2N(CH3)C6H3)3COH, which is oxidized in acid to give the dye.[2]

Use as dye and stain

[edit]

New fuchsine is used to dye polyacrylonitrile, paper, and leather.[citation needed] In biology, it can be used for staining acid-fast organisms, e.g. by Ziehl–Neelsen stain, and for making Schiff's reagent. As a primary amine, the dye can be diazotized in the laboratory, and the resulting diazonium salt used as a trapping agent in enzyme histochemistry.[3]

Etymology

[edit]

The name fuchsine recognizes Leonhart Fuchs.

See also

[edit]

References

[edit]
  1. ^ Horobin RW, Kiernan JA (2002) Conn's Biological Stains, 10th ed. Oxford: BIOS.
  2. ^ Thetford, Dean; Updated By Staff (2013). "Triphenylmethane and Related Dyes". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2018091620080520.a01.pub2. ISBN 978-0471238966.
  3. ^ Lojda Z, Gossrau R, Schiebler TH (1979) Enzyme Histochemistry. A Laboratory Manual. Berlin: Springer-Verlag.
[edit]
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