Acifluorfen

Reported in EPA TSCA Inventory.

The Acifluorofen, with the CAS registry number 50594-66-6 and EINECS registry number 256-634-5, has the systematic name of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid. And the molecular formula of this chemical is C₁₄H₇ClF₃NO₅. It belongs to the product categories of Organics and Herbicide, and should be stored at 0-6°C. What's more, it is a protoporphyrinogen oxidase inhibitor, and it often used as Fluorinated ether herbicides.

The physical properties of Acifluorofen are as following: (1)ACD/LogP: 4.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.34; (4)ACD/LogD (pH 7.4): 1.2; (5)ACD/BCF (pH 5.5): 1.16; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 5.42; (8)ACD/KOC (pH 7.4): 3.94; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 81.35 Å²; (13)Index of Refraction: 1.575; (14)Molar Refractivity: 76.04 cm³; (15)Molar Volume: 229.8 cm³; (16)Polarizability: 30.14×10^-24cm³; (17)Surface Tension: 49.3 dyne/cm; (18)Density: 1.573 g/cm³; (19)Flash Point: 209.2 °C; (20)Enthalpy of Vaporization: 71.32 kJ/mol; (21)Boiling Point: 422.4 °C at 760 mmHg; (22)Vapour Pressure: 6.89E-08 mmHg at 25°C.

Preparation of Acifluorofen: It can start with the reaction between equimolar 3,4-dichlorobenzotrifluoride and 3-hydroxybenzoic acid in the presence of KOH. The reaction also needs solvent dimethyl sulfoxide, and the reaction time is 22hours with the temperature of 138-144°C. Then nitrify the result with potassium nitrate-sulfate in the solvent methylene dichloride, and you can get the desired product Acifluorofen.

You should be cautious while dealing with this chemical. It irritates skin, and harmful if swallowed. And it also has the risk of serious damage to eyes. What's more, it is very toxic to aquatic organisms, and may cause long-term adverse effects in the aquatic environment. Therefore, you had better take the following instructions: Wear eye/face protection; Avoid contact with skin; This material and/or its container must be disposed of as hazardous waste; Avoid release to the environment. Refer to special instructions safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc2cc(ccc2Oc1cc(C(=O)O)c([N+]([O-])=O)cc1)C(F)(F)F
(2)InChI: InChI=1/C14H7ClF3NO5/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21/h1-6H,(H,20,21)
(3)InChIKey: NUFNQYOELLVIPL-UHFFFAOYAH

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
duck	LD50	oral	2821mg/kg (2821mg/kg)		Pesticide Manual. Vol. 9, Pg. 6, 1991.
mouse	LD50	oral	1370mg/kg (1370mg/kg)		Pesticide Manual. Vol. 9, Pg. 6, 1991.
quail	LD50	oral	325mg/kg (325mg/kg)		Pesticide Manual. Vol. 9, Pg. 6, 1991.
rabbit	LD50	skin	3680mg/kg (3680mg/kg)		Pesticide Manual. Vol. 9, Pg. 6, 1991.
rat	LC50	inhalation	> 6900mg/m3/4H (6900mg/m3)		Pesticide Manual. Vol. 9, Pg. 6, 1991.
rat	LD50	oral	1370mg/kg (1370mg/kg)		Pesticide Manual. Vol. 9, Pg. 6, 1991.