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  • 2,2'-Thiobis(4,6-dichlorophenol)

  • 2,2'-Thiobis(4,6-dichlorophenol)

    Catalog Number
    ACM97187
    CAS Number
    97-18-7
    Product Name
    2,2'-Thiobis(4,6-dichlorophenol)
    Structure
    Category
    Monomers; Polymers
    Description
    2,2'-thiobis(4,6-dichlorophenol) appears as white or grayish white crystalline powder with a very faint aromatic or phenolic odor. (NTP, 1992)
    IUPAC Name
    2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenyl)sulfanylphenol
    Molecular Weight
    356g/mol
    Molecular Formula
    C12H6Cl4O2S
    Canonical SMILES
    C1=C(C=C(C(=C1SC2=C(C(=CC(=C2)Cl)Cl)O)O)Cl)Cl
    InChI
    InChI=1S/C12H6Cl4O2S/c13-5-1-7(15)11(17)9(3-5)19-10-4-6(14)2-8(16)12(10)18/h1-4,17-18H
    InChI Key
    JFIOVJDNOJYLKP-UHFFFAOYSA-N
    Melting Point
    365.9 to 367.7 °F (NTP, 1992);188.0 °C;188 °C
    Density
    1.73 (NTP, 1992);1.73 at 25 °C/4 °C
    Solubility
    less than 1 mg/mL at 73° F (NTP, 1992);1.12e-05 M;Sol in dil caustic soln. A 4% sodium hydroxide soln will dissolve 16.2% bithionol. 15.0 g/100 ml acetone; 19.0 g/100 ml polysorbate 80; 72.5 g/100 ml dimethylacetamide; 5.0 g/100 ml lanolin at 42 °C; 4.0 g/100 ml pine oil; 1.0 g/100 ml corn oil; 0.5 g/100 ml propylene glycol; 0.3 g/100 ml 70% ethanol;Freely sol in ether; sol in chloroform and dilute soln of fixed alkali hydroxides;In water, 4 mg/L at 25 °C
    Application
    2,2'-Thiobis(4,6-dichlorophenol), known as Bithionol, serves a critical role as an anthelmintic and antimicrobial agent. It was historically included in soaps and cosmetic products for its ability to inhibit microbial growth. However, its usage in topical applications was discontinued due to adverse effects like contact photodermatitis. Despite this, Bithionol remains an important medical tool for managing parasitic infections. It is particularly effective as a fasciolicide and taeniacide, making it the preferred treatment for infestations caused by the liver fluke Fasciola hepatica and the lung fluke Paragonimus westermani. While Niclosamide is often favored for tapeworm treatments, Bithionol's unique properties make it an essential option for addressing specific parasitic challenges.
    Color/Form
    White or grayish-white, crystalline powder
    Complexity
    282
    Covalently-Bonded Unit Count
    1
    EC Number
    202-565-0
    Exact Mass
    355.881311g/mol
    Formal Charge
    0
    Heavy Atom Count
    19
    Log P
    log Kow = 5.91 (est)
    MeSH Entry Terms
    Bithionol;Bitin
    Monoisotopic Mass
    353.884261g/mol
    NSC Number
    47129;9872
    Odor
    Odorless or with slight aromatic or phenolic odor
    Other Experimental
    Henry's Law constant = 1.0X10-13 atm-cu m/mol at 25 °C (est);Hydroxyl radical reaction rate constant = 8.8X10-12 cu cm/molec-sec at 25 °C (est);log Kow= 4.13 /Bithionol sulfoxide/
    Rotatable Bond Count
    2
    UNII
    AMT77LS62O
    UN Number
    2811
    Vapor Pressure
    1.1e-09 mm Hg at 99 °F (NTP, 1992);1.1X10-9 mm Hg at 37 °C
    XLogP3
    5.8
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