Product Name
2,2'-Thiobis(4,6-dichlorophenol)
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 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
Covalently-Bonded Unit Count
1
Exact Mass
355.881311g/mol
Log P
log Kow = 5.91 (est)
MeSH Entry Terms
Bithionol;Bitin
Monoisotopic Mass
353.884261g/mol
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/
Vapor Pressure
1.1e-09 mm Hg at 99 °F (NTP, 1992);1.1X10-9 mm Hg at 37 °C