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2,2'-Thiobis(4,6-dichlorophenol)

Name: 2,2'-Thiobis(4,6-dichlorophenol)
SKU: ACM97187
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Catalog NumberACM97187

CAS Number97-18-7

CategoryMonomers; 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

EC Number

202-565-0

Exact Mass

355.881311g/mol

Formal Charge

Heavy Atom Count

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

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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