Bithionol
Title: Bithionol
CAS Registry Number: 97-18-7
CAS Name: 2,2¢-Thiobis[4,6-dichlorophenol]
Additional Names: TBP; bis(2-hydroxy-3,5-dichlorophenyl)sulfide
Manufacturers' Codes: XL-7
Trademarks: Bithin; Lorothidol
Molecular Formula: C12H6Cl4O2S
Molecular Weight: 356.05
Percent Composition: C 40.48%, H 1.70%, Cl 39.83%, O 8.99%, S 9.01%
Literature References: Prepn from 2,4-halo substituted phenol with S halides: Muth, DE 583055 (1933 to I. G. Farbenind.), C.A. 28, 179 (1934); Copper, Godfrey, US 2849494 (1958 to Monsanto). Comprehensive review and bibliography: Shumard et al., Soap Sanit. Chem. 29, no. 1, 34-37, 90 (1953). Anthelmintic activity of the sulfoxide: J. Guilhon, M. Graber, Bull. Acad. Vet. Fr. 52, 225 (1979). Metabolism of the sulfoxide in humans: M. Sakamoto et al., J. Toxicol. Sci. 6, 307 (1981).
Properties: Crystals, mp 188°. d425 1.73. pK1 4.82; pK2 10.50. Vapor press. at 37°: 1.1 ´ 10-9 mm Hg. Practically insol in water (0.0004% at 25°). Sol in dil caustic solns. A 4% NaOH soln will dissolve 16.2% bithionol. Soly (g/100 ml): acetone 15.0; polysorbate 80 19.0; dimethylacetamide 72.5; lanolin at 42° 5.0; pine oil 4.0; corn oil 1.0; propylene glycol 0.5; 70% ethanol 0.3.
Melting point: mp 188°
pKa: pK1 4.82; pK2 10.50
Density: d425 1.73
 
Derivative Type: Sodium salt
CAS Registry Number: 6385-58-6
Additional Names: Bithionolate sodium
Trademarks: Vancide BN (Vanderbilt)
Molecular Formula: C12H4Cl4Na2O2S
Molecular Weight: 400.02
Percent Composition: C 36.03%, H 1.01%, Cl 35.45%, Na 11.49%, O 8.00%, S 8.02%
Literature References: Harvey et al., US 3024163 (1962 to Vanderbilt Co.).
 
Derivative Type: Sulfoxide
Additional Names: BTS
Trademarks: Bitin-S (Tanabe Seiyaku); Disto-5 (Cogla)
Molecular Formula: C12H6Cl4O3S
Molecular Weight: 372.05
Percent Composition: C 38.74%, H 1.63%, Cl 38.12%, O 12.90%, S 8.62%
 
Use: Surfactant-formulated antimicrobial against bacteria, molds and yeast. In cosmetics. Proposed as agricultural fungicide.
Therap-Cat: Anti-infective (topical).
Therap-Cat-Vet: Anthelmintic; antiseptic.
Keywords: Antiseptic/Disinfectant; Phenols.

Others monographs:
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Spandex2-Cyclohexyl-4,6-dinitrophenolIbopaminePyrazinoic Acid
Thallium OxideAllylamineStarch, SolubleDiclosulam
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