Fenticlor

Fenticlor
Clinical data
Routes of; administration	topical
Identifiers
	IUPAC name Bis[2-hydroxy-5-chlorophenyl] sulfide;
CAS Number	97-24-5;
PubChem CID	7329;
ChemSpider	7052;
UNII	D61659OVD0;
KEGG	D04164;
ChEMBL	ChEMBL473535;
CompTox Dashboard (EPA)	DTXSID4026137 ;
ECHA InfoCard	100.002.336
Chemical and physical data
Formula	C12H8Cl2O2S
Molar mass	287.15 g·mol−1
Melting point	174 °C (345 °F)

Fenticlor (also spelled fentichlor) is an antibacterial and antifungal agent for topical use. It is an antimicrobial agent. It is also used in veterinary medicine.

Synthesis

It is prepared by the AlCl₃-catalyzed reaction of 4-chlorophenol with sulfur dichloride.^[1] It can also be prepared by chlorination of bis[2-hydroxyphenyl]sulfide.^[2]^[3]

Safety

The LD₅₀ (rats, oral) of fenticlor is 3250 mg/kg.^[1] It may cause photosensitivity.^[4]

References

^ ^a ^b Fiege H, Voges HW, Hamamoto T, Umemura S, Iwata T, Miki H, Fujita Y, Buysch HJ, Garbe D, Paulus W (2007). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.
^ DE 568944, Muth F, "Verfahren zur Darstellung von Bis-(halogen-oxyaryl)-sulfiden", issued 1931, assigned to I. G. Farben
^ Dunning F, Dunning B, Drake WE (1931). "Preparation and Bacteriological Study of Some Symmetrical Organic Sulfides". Journal of the American Chemical Society. 53 (9): 3466–3469. doi:10.1021/ja01360a035.
^ Burry JN (June 1974). "Letter: Fenticlor, actinic reticuloid, and antihistamines". British Medical Journal. 2 (5918): 556–7. doi:10.1136/bmj.2.5918.556-c. PMC 1610938. PMID 4152080.

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[a-1] Fiege H, Voges HW, Hamamoto T, Umemura S, Iwata T, Miki H, Fujita Y, Buysch HJ, Garbe D, Paulus W (2007). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.

[2] DE 568944, Muth F, "Verfahren zur Darstellung von Bis-(halogen-oxyaryl)-sulfiden", issued 1931, assigned to I. G. Farben

[3] Dunning F, Dunning B, Drake WE (1931). "Preparation and Bacteriological Study of Some Symmetrical Organic Sulfides". Journal of the American Chemical Society. 53 (9): 3466–3469. doi:10.1021/ja01360a035.

[pmid4152080-4] Burry JN (June 1974). "Letter: Fenticlor, actinic reticuloid, and antihistamines". British Medical Journal. 2 (5918): 556–7. doi:10.1136/bmj.2.5918.556-c. PMC 1610938. PMID 4152080.

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