2- Trifluoromethyl-4-nitrophenol

Trifluoromethyl-4-nitrophenol [88-30-2] M 162.1, m 81°, pK si 6.1. Crystd from benzene or from pet ether/ benzene mixture. 

The main products of photolysis of 3-trifluoromethyl-4-nitrophenol are 2,5 dihydroxy-benzoate produced by hydrolytic loss of the nitro group and oxidation of the trifluoromethyl group, together with a compound identified as a condensation product of the original compound and the dihydroxybenzoate (Figure 1.5) (Carey and Cox 1981). 

Carey JH, ME Cox (1981) Photodegradation of the lampricide 3-trifluoromethyl-4-nitrophenol (TFM). 1. Pathway of the direct photolysis in solution. J Great Lakes Res 7 234-241. 

A series of dibenzo[l,4]dioxins bearing nitro and trifluoromethyl substituents in one ring and chlorine in the other was synthesized for comparison with impurities in commercial samples of the lampricide 3-trifluoromethyl-4-nitrophenol, and to assess their ability to induce MFO activity (Hewitt et al. 1998). Although they appeared to be relatively weak inducers, there were other unidentified components that were highly active. 

Hewitt LM, JH Carey, KR Munkittrick, JL Parrott, KR Solomon, MR Servos (1998) Identification of chloro-nitro-trifluoromethyl-substituted dibenzo-/ -dioxins in lampricide formulations of 3-trifluoromethyl-4-nitrophenol assessment to induce mixed function oxidase activity. Environ Toxicol Chem 17 941-950. 

Laboratory trials during lampricide application (0.5-5.8 mg/L, 24-h exposure) with rainbow trout confirmed that field formulations of lampricides induce hepatic mixed function oxygenase enzymes activity. Mixed function oxygenase induction was associated with the 3-trifluoromethyl-4-nitrophenol formulation, and not the 2, 5-dichloroU -nitrosalicylanilidc (Bayer 73) component of the field application. Bioassays were successfully confirmed with HPLC [78]. 

Lech, J. J. Isolation and identification of 3"trifluoro-methyl-4-nitrophenyl glucuronide from bile of rainbow trout exposed to 3-trifluoromethyl-4-nitrophenol. Toxicol. Appl. Pharmacol. (1973), 24 114-124. 

Sills, J. B., Allen, J. L. Accumulation and loss of residues of 3-trifluoromethyl-4-nitrophenol (TFM) in fish muscle laboratory studies. U.S. Fish Wildl. Serv., Invest. Fish. Control (1975), 65, 10 pp. 

Trifluoromethyl-4-nitrophenol(TMF) Sea lamprey Trout Glucuronide Bile 11... 

Nitro-trifluoromethyl-PCDEs and hydroxy-trifluoromethyl-PCDEs have been detected as impurities in 3-trifluoromethyl-4-nitrophenol (TFM), which is a field formulation of a lampricide [32]. This lampricide has been applied to protect salmonids from sea lampreys in streams since the 1950s. 

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