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    2-Naphthol - Wikipedia

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    2-Naphthol is a colorless crystalline solid that is produced through sulfonation and hydrolysis of naphthalene. It is used to produce dyes and other compounds. Some of its properties and reactions are described.

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    2-Naphthol - Wikipedia

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    mwimaandrew2
    40 views19 pages
    2-Naphthol is a colorless crystalline solid that is produced through sulfonation and hydrolysis of naphthalene. It is used to produce dyes and other compounds. Some of its properties and reactions are described.

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    2-Naphthol is a colorless crystalline solid that is produced through sulfonation and hydrolysis of naphthalene. It is used to produce dyes and other compounds. Some of its properties and reactions are described.

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    © All Rights Reserved
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    Download as pdf or txt
    40 views19 pages

    2-Naphthol - Wikipedia

    Uploaded by

    mwimaandrew2
    2-Naphthol is a colorless crystalline solid that is produced through sulfonation and hydrolysis of naphthalene. It is used to produce dyes and other compounds. Some of its properties and reactions are described.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    of 19

    2-Naphthol

    2-Naphthol, or β-naphthol, is a fluorescent colorless (or occasionally yellow) crystalline solid


    with the formula C10H7OH. It is an isomer of 1-naphthol, differing by the location of the hydroxyl
    group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, but more
    reactive. Both isomers are soluble in simple alcohols, ethers, and chloroform. 2-Naphthol is a
    widely used intermediate for the production of dyes and other compounds.

    Production
    Traditionally, 2-naphthol is produced by a two-step process that begins with the sulfonation of
    naphthalene in sulfuric acid:[2]

    C10H8 + H2SO4 → C10H7SO3H + H2O


    The sulfonic acid group is then cleaved in molten sodium hydroxide:

    C10H7(SO3H) + 3 NaOH → C10H7ONa +


    Na2SO3 + 2 H2O
    Neutralization of the product with acid gives 2-naphthol.
    2-Naphthol can also be produced by a method
    analogous to the cumene process.[2]
    2-Naphthol
    2-Naphthol-
    derived dyes
    The Sudan dyes are popular dyes noted for
    being soluble in organic solvents. Several of
    the Sudan dyes are derived from 2-naphthol
    by coupling with diazonium salts.[3] Sudan
    dyes I–IV and Sudan Red G consist of arylazo-
    substituted naphthols.

    Selected 2-
    Names
    Naphthol-derived
    Preferred IUPAC
    dyes
    name
    Naphthalen-2-ol

    Other names
    2-
    Hydroxynaphthale
    ne; 2-
    Naphthalenol;
    beta-Naphthol;
    Naphth-2-ol

    Identifiers

    CAS 135-19-3
    Sudan I Number
    (https://c
    ommonc
    hemistry.
    cas.org/
    detail?ca
    s_rn=135
    -19-3)
    Sudan II
    3D Interactive
    model
    image (htt
    (JSmol)
    ps://chem
    apps.stola
    f.edu/jmo
    l/jmol.ph
    p?model=
    Oc2ccc1
    c%28cccc
    Sudan III 1%29c2)
    Interactive
    image (htt
    ps://chem
    apps.stola
    f.edu/jmo
    l/jmol.ph
    Sudan IV p?model=
    c1ccc2c
    c%28ccc2
    c1%29O)
    Beilstein 742134
    Reference

    ChEBI CHEBI:10432
    (https://ww
    w.ebi.ac.uk/c
    Oil Red O hebi/searchI
    d.do?chebiId
    =10432)

    ChEMBL ChEMBL14
    26 (https://w
    ww.ebi.ac.u
    k/chembldb
    Naphthol AS
    index.php/c
    mpound/ins
    Reactions pect/ChEM
    Some reactions of 2-naphthol are explicable
    L14126)
    with reference to its tautomerism, which
    produces a small amount of the keto
    tautomer. ChemSpi 8341 (htt
    der ps://ww
    Tautomeric equilibrium for beta-naphthol w.chems
    One consequence of this tautomerism is the pider.co
    Bucherer reaction, the ammonolysis of 2-
    naphthol to give 2-aminonaphthalene. m/Chemi
    2-Naphthol can be oxidatively coupled to form
    BINOL, a C2-symmetric ligand popularized for
    cal-Struc
    use in asymmetric catalysis.
    ture.834
    1.html)

    ECHA 100.004.71
    InfoCard (https://ech
    a.europa.e
    u/substanc
    -informatio
    n/-/substan
    ceinfo/100.
    004.712)
    EC 205-182-
    Number 7

    Gmelin 27395
    Reference

    KEGG C11713
    (https://
    www.keg
    g.jp/entr
    y/C1171
    3)

    PubChem 8663 (htt


    CID
    ps://pub
    chem.nc
    bi.nlm.ni
    h.gov/co
    mpound/
    8663)
    RTECS QL2975000
    number

    UNII P2Z71CIK5H
    (https://prec
    ision.fda.go
    v/uniisearc
    h/srs/unii/P
    2Z71CIK5
    H)

    UN 3077
    number

    CompTox DTXSID502
    Dashboard
    061 (https:/
    (EPA)
    comptox.ep
    a.gov/dash
    oard/chem
    al/details/D
    XSID50270
    1)

    InChI
    InChI=1S/C10H8
    O/c11-10-6-5-8
    -3-1-2-4-9(8)7-1
    0/h1-7,11H
    Key: JWAZRIHNYR
    IHIV-UHFFFAO
    YSA-N
    InChI=1/C10H8O/
    c11-10-6-5-8-3-
    1-2-4-9(8)7-10/
    h1-7,11H
    Key: JWAZRIHNYR
    IHIV-UHFFFAO
    YAV

    SMILES
    Oc2ccc1c(cccc1)
    c2
    c1ccc2cc(ccc2c1)
    O

    Properties

    Chemical C10H8O
    formula

    Molar 144.173 g·m


    mass ol−1

    Appeara Colorless
    nce crystalline
    solid

    Density 1.280
    g/cm3

    Melting 121 to
    point 123 °C
    (250 to
    253 °F;
    394 to
    396 K)

    Boiling 285 °C
    point (545 °F;
    558 K)

    Solubility 0.74 g/L


    in water

    Acidity 9.51
    (pKa)

    Magnetic -98.25·10−6
    susceptibility 3
    cm /mol
    (χ)

    Hazards

    Occupational safety
    and health
    (OHS/OSH):
    Main Harmful
    hazards
    when
    inhaled or
    swallowed
    dangerous
    to
    environme
    esp. aquat
    organisms

    GHS labelling:

    Pictograms

    Signal Warning
    word

    Hazard H302,
    statements
    H332,
    H400
    Precautionary
    P261, P26
    statements
    P270, P27
    P273,
    P301+P31
    P304+P31
    P304+P34
    P312, P33
    P391, P50

    NFPA 2
    1
    0

    704
    (fire dia
    mond)

    Flash 161 °C
    point (322 °F;
    434 K)[1]
    Except where
    otherwise noted,
    data are given for
    materials in their
    standard state (at
    25 °C [77 °F],
    100 kPa).
    verify (https://en.w
    ikipedia.org/w/inde
    x.php?title=Special:
    ComparePages&rev
    1=477214746&page
    2=2-Naphtho
    l) (what is ?)
    Infobox references
    2-Naphthol converts to 2-naphthalenethiol by reaction with dimethylthiocarbamoyl chloride via
    the Newman–Kwart rearrangement.[4] The OH→Br conversion has been described.[5]

    Electrophilic attack occurs characteristically at the 1-position as indicated by nitrosylation to


    give 1-nitroso-2-naphthol.[6] Bromination[7] and alkylations proceed with similar regiochemistry.[8]
    Ring-opening reactions have been documented.[9]

    Safety
    2-Naphthol has been described as "moderately toxic.[2]

    References

    1. "MSDS safety data for 2-naphthol" (https://


    web.archive.org/web/20110303133020/htt
    ps://msds.chem.ox.ac.uk/NA/2-naphthol.ht
    ml) . Archived from the original (https://ms
    ds.chem.ox.ac.uk/NA/2-naphthol.html) on
    3 March 2011.
    2. Booth, Gerald (2005). "Naphthalene
    Derivatives". Ullmann's Encyclopedia of
    Industrial Chemistry. Weinheim: Wiley-VCH.
    doi:10.1002/14356007.a17_009 (https://do
    i.org/10.1002%2F14356007.a17_009) .
    ISBN 978-3527306732.. full-text PDF (http
    s://pdfslide.net/documents/ullmanns-ency
    clopedia-of-industrial-chemistry-naphthalen
    e-derivatives.html)
    3. Booth, Gerald; Zollinger, Heinrich; McLaren,
    Keith; Sharples, William G.; Westwell, Alan
    (2000). "Dyes, General Survey". Ullmann's
    Encyclopedia of Industrial Chemistry. Wiley-
    VCH. doi:10.1002/14356007.a09_073 (http
    s://doi.org/10.1002%2F14356007.a09_07
    3) . ISBN 9783527306732.
    4. Melvin S. Newman; Frederick W. Hetzel
    (1971). "Thiophenols from Phenols: 2-
    Naphthalenethiol" (https://www.orgsyn.org/
    demo.aspx?prep=CV6P0824) . Organic
    Syntheses. 51: 139.
    doi:10.15227/orgsyn.051.0139 (https://doi.
    org/10.15227%2Forgsyn.051.0139) .
    5. J. P. Schaefer; Jerry Higgins; P. K. Shenoy
    (1969). "2-Bromonaphthalene". Organic
    Syntheses. 49: 6.
    doi:10.15227/orgsyn.049.0006 (https://doi.
    org/10.15227%2Forgsyn.049.0006) .
    6. Marvel, C. S.; Porter, P. K. (1922). "Nitroso-β-
    Naphthol". Organic Syntheses. 2: 61.
    doi:10.15227/orgsyn.002.0061 (https://doi.
    org/10.15227%2Forgsyn.002.0061) .
    7. C. Frederick Koelsch (1940). "6-Bromo-2-
    Naphthol". Organic Syntheses. 20: 18.
    doi:10.15227/orgsyn.020.0018 (https://doi.
    org/10.15227%2Forgsyn.020.0018) .
    8. Alfred Russell Luther B. Lockhart (1942). "2-
    Hydroxy-1-Naphthaldehyde". Organic
    Syntheses. 22: 63.
    doi:10.15227/orgsyn.022.0063 (https://doi.
    org/10.15227%2Forgsyn.022.0063) .
    9. G. A. Page, D. S. Tarbell (1954). "β-(o-
    Carboxyphenyl)propionic Acid". Organic
    Syntheses. 34: 8.
    doi:10.15227/orgsyn.034.0008 (https://doi.
    org/10.15227%2Forgsyn.034.0008) .

    External links

    NIST Chemistry WebBook 2-


    Naphthalenol (http://webbook.nist.gov/
    cgi/cbook.cgi?Name=2-naphthol&Units=
    SI)
    "Napthols" (https://en.wikisource.org/wi
    ki/1911_Encyclop%C3%A6dia_Britannic
    a/Napthols) . Encyclopædia Britannica.
    Vol. 19 (11th ed.). 1911. pp. 168–169.

    Retrieved from
    "https://en.wikipedia.org/w/index.php?title=2-
    Naphthol&oldid=1197756250"

    This page was last edited on 21 January 2024, at


    20:41 (UTC). •
    Content is available under CC BY-SA 4.0 unless
    otherwise noted.

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