42874-01-1

Basic information

• Product Name: NITROFLUORFEN
• Synonyms: 2-Chloro-4-trifluoromethylphenyl 4-nitrophenyl ether;2-Chloro-α,α,α-trifluoro-p-tolyl p-nitrophenyl ether;NITROFLUORFEN;2-chloro-1-(4-nitrophenoxy)-4-trifluoromethylbenzene;ether,2-chloro-alpha,alpha,alpha-trifluoro-p-tolylp-nitrophenyl;nitrofluorfene;rh2512;rh-2512
• CAS NO: 42874-01-1
• Molecular Formula: C₁₃H₇ClF₃NO₃
• Molecular Weight: 317.65
• Mol File: 42874-01-1.mol

Chemical Properties

• Melting Point: 68°C
• Boiling Point: 329.8°C at 760 mmHg
• Flash Point: 153.3°C
• Appearance: /
• Density: 1.4978 (estimate)
• Vapor Pressure: 0.000332mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: NITROFLUORFEN(CAS DataBase Reference)
• NIST Chemistry Reference: NITROFLUORFEN(42874-01-1)
• EPA Substance Registry System: NITROFLUORFEN(42874-01-1)

Safety Data

• Hazardous Substances Data: 42874-01-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H7ClF3NO3/c14-11-7-8(13(15,16)17)1-6-12(11)21-10-4-2-9(3-5-10)18(19)20/h1-7H

Upstream product

• 50594-66-6 acifluorfen 
• 100-02-7 4-nitro-phenol 
• 78068-85-6 3-chloro-4-fluoro benzotrifluoride 
• 402-45-9 4-hydroxybenzotrifluoride 
• 42874-98-6 4-(2-chloro-4-trifluoromethylphenoxy)-benzene 

Downstream Products

• 42874-63-5 5-(o-chloro-p-trifluoromethyl-phenoxy)-2-nitrophenol 
• 55407-28-8 p-[(2-chloro-α,α,α-trifluoro-p-tolyl)oxy]aniline 

Relevant articles and documents

Photochemical degradation of acifluorfen in aqueous solution

To elucidate the photochemical behavior of diphenyl ether herbicides in superficial waters, the photodegradation of acifluorfen, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid (CAS Registry No. 50594-66-6), was studied in water and acetonitrile. All experiments were carried out under laboratory conditions using a solar simulator (xenon arc) or jacket Pyrex reaction cell equipped with a 125 W high-pressure mercury lamp. The calculated polychromatic quantum efficiencies (Φsolvent) of acifluorfen in different solvents are as follows (units are degraded molecules photon-1): Φwater = 10-4, Φacetronitile = 10-4, Φmethanol = 10-4, and Φhexane = 10-2. The results obtained in this work are in good agreement with the literature value of monochromatic quantum yield. HPLC-MS analysis (APCI and ESI in positive and negative modes) was used to identify acifluorfen photoproducts. These results suggest that the photodegradation of acifluorfen proceeds via a number of reaction pathways: (1) decarboxylation, (2) dehalogenation, (3) substitution of chlorine group by hydroxyl or hydrogen groups, and (4) cleavage of ether linkage, giving phenols. Photorearrangement products were studied by other investigators. No such products were observed. In addition, it was found that the trifluoro functional group on acifluorfen was not affected by any transformation, and no products of a nitro group reduction were found.

Photochemical transformation of acifluorfen under laboratory and natural conditions

Acifluorfen was irradiated in pure water at various excitation wavelengths and pH values. Numerous photoproducts were obtained which were identified by [1H]NMR and /or HPLC-MS/MS. The main reaction pathways were photo-decarboxylation, photo-cleavage of the ether bonding with formation of phenolic compounds, photo-dechlorination and photo-Claisen type rearrangement. Decarboxylation was observed in acidic and neutral media whereas cleavage of the ether bonding dominated in basic media. The photo-Claisen type rearrangement only occurred on excitation at short wavelengths. The quantum yield of photolysis was significantly lower at 313nm (6.1 × 10-5) than at 254nm (2.0 × 10-3). The photoreactivity of acifluorfen was then studied in conditions approaching environmental conditions. Acifluorfen was dissolved in pure water, in water containing humic substances or in a natural water, and exposed to solar light in June at Clermont-Ferrand (latitude 46°N). In pure water, the half-life was estimated at 10 days and photo-decarboxylation accounted for 30% of the conversion. The presence of humic substances (10mg litre-1) did not affect the rate of photo-transformation. However, the half-life of acifluorfen dissolved in the natural water was only 6.8 days.

Preparation of diphenylethers

The present invention is directed to the preparation of 3-hydroxy diphenylethers and with the use of such 3-hydroxy diphenylethers in the preparation of 3-alkoxy diphenylethers. More particularly, the present invention is concerned with the preparation of 3-hydroxy-4-nitrodiphenylethers and with the use of such 3-hydroxy-4-nitrodiphenylethers in the preparation of 3-alkoxy-4-nitrodiphenylethers. Many of the 3-hydroxy-4-nitrodiphenylethers and the 3-alkoxy-4-nitrodiphenylethers exhibit herbicidal activity.