3070. 4,5-Dichloro-2-octyl-3-isothiazolone

Nomenclature

CAS number: 64359-81-5
4,5-dichloro-2-octyl-3(2H)-isothiazolone; 2-n-octyl-4,5-dichloro-1-isothiazolin-3-one; 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one; DCOI; C-9211; RH-5287; Sea-Nine (Rohm & Haas).
C11H17Cl2NOS; mol wt 282.23.
C 46.81%, H 6.07%, Cl 25.12%, N 4.96%, O 5.67%, S 11.36%.

Description and 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).

Chemical structure

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).

Use

Marine antifoulant.