4,5-Dichloro-2-octyl-3-isothiazolone
Structural Formula Vector Image
Title: 4,5-Dichloro-2-octyl-3-isothiazolone
CAS Registry Number: 64359-81-5
CAS Name: 4,5-dichloro-2-octyl-3(2H)-isothiazolone
Additional Names: 2-n-octyl-4,5-dichloro-1-isothiazolin-3-one; 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one; DCOI
Manufacturers' Codes: C-9211; RH-5287
Trademarks: Sea-Nine (Rohm & Haas)
Molecular Formula: C11H17Cl2NOS
Molecular Weight: 282.23
Percent Composition: C 46.81%, H 6.07%, Cl 25.12%, N 4.96%, O 5.67%, S 11.36%
Literature References: Environmentally friendly marine antifouling agent. Prepn: E. D. Weiler et al., J. Heterocycl. Chem. 14, 627 (1977). Physical properties and ecological risk assessment: W. D. Shade et al., ASTM Spec. Tech. Publ. STP 1216, 381 (1993). HPLC analysis and persistence in seawater and sediment: A. Jacobson et al., ACS Symp. Ser. 522, 127 (1993). Review: G. L. Willingham, A. H. Jacobson, ibid. 640, 224-233 (1996).
Properties: Crystals from hexane, mp 44-46°. Technical product is reported as tan-to-brown waxy solid with pungent aromatic odor, mp 40-41°. d25 1.28 g/ml. Vapor pressure (25°): 7.4 ´ 10-6 mm Hg. Log P (octanol/water): 2.85 (Willingham, Jacobson); also reported as 4.5 (Shade). Miscible in most organic solvents. Soly (ppm): 6.5 in deionized water; 4.7 in synthetic seawater. LC50 (96 hr) in bluegill sunfish, adult bay mussel, fiddler crab: 14, 850, 1312 ppb (Willingham, Jacobson).
Melting point: mp 44-46°; mp 40-41°
Log P: Log P (octanol/water): 2.85 (Willingham, Jacobson); also reported as 4.5 (Shade)
Density: d25 1.28 g/ml
Toxicity data: LC50 (96 hr) in bluegill sunfish, adult bay mussel, fiddler crab: 14, 850, 1312 ppb (Willingham, Jacobson)
Use: Marine antifoulant.

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