1306. Bithionol

Nomenclature

CAS number: 97-18-7
2,2′-Thiobis[4,6-dichlorophenol]; TBP; bis(2-hydroxy-3,5-dichlorophenyl)sulfide; XL-7; Bithin; Lorothidol.
C12H6Cl4O2S; mol wt 356.05.
C 40.48%, H 1.70%, Cl 39.83%, O 8.99%, S 9.01%.

Description and 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).

Chemical structure

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.

Derivative

Sodium salt.

Nomenclature

CAS number: 6385-58-6
Bithionolate sodium; Vancide BN (Vanderbilt).
C12H4Cl4Na2O2S; mol wt 400.02.
C 36.03%, H 1.01%, Cl 35.45%, Na 11.49%, O 8.00%, S 8.02%.

Description and references

Harvey et al., US 3024163 (1962 to Vanderbilt Co.).

Derivative

Sulfoxide.

Nomenclature

BTS; Bitin-S (Tanabe Seiyaku); Disto-5 (Cogla).
C12H6Cl4O3S; mol wt 372.05.
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.

Therapeutic Category

Anti-infective (topical).

Therapeutic Category (Veterinary)

Anthelmintic; antiseptic.

Keywords

Antiseptic/Disinfectant; Phenols