New fuchsine

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New fuchsine
Names
Other names
New fuchsin; Magenta III; Basic Violet 2; C.I. 42520
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.019.847 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 mass365.91 g·mol−1
Appearanceviolet 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. {{cite book}}: |last2= has generic name (help)
  3. ^ Lojda Z, Gossrau R, Schiebler TH (1979) Enzyme Histochemistry. A Laboratory Manual. Berlin: Springer-Verlag.
[edit]
    New fuchsine
    Names
    Other names
    New fuchsin; Magenta III; Basic Violet 2; C.I. 42520
    Identifiers
    • 3248-91-7
    3D model (JSmol)
    • Interactive image
    ChEBI
    • CHEBI:87671 checkY
    ChEMBL
    • ChEMBL1979779
    ChemSpider
    • 17578
    ECHA InfoCard100.019.847
    EC Number
    • 221-831-7
    • 18611
    UNII
    • A051F48W36 base
    • DTXSID80879817
    • 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 mass365.91 g·mol−1
    Appearanceviolet 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

    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

    The name fuchsine recognizes Leonhart Fuchs.

    See also

    References

    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. {{cite book}}: |last2= has generic name (help)
    3. ^ Lojda Z, Gossrau R, Schiebler TH (1979) Enzyme Histochemistry. A Laboratory Manual. Berlin: Springer-Verlag.
    • New Fuchsin - StainsFile
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