1644-88-8

Basic information

• Product Name: 2-(Trifluoromethoxy)nitrobenzene
• Synonyms: 2-NITRO TRIFLUOROMETHOXY BENZENE;2-(TRIFLUOROMETHOXY)NITROBENZENE;1-Nitro-2-(trifluoromethoxy)benzene;2-Nitro-alpha,alpha,alpha-trifluoroanisole, 2-Nitrophenyl trifluoromethyl ether;1-Nitro-2-[(trifluoroMethyl)oxy]benzene;α,α,α-trifluoro-o-nitroanisole;2-(TrifluoroMrthoxy)nitrobebzene
• CAS NO: 1644-88-8
• Molecular Formula: C₇H₄F₃NO₃
• Molecular Weight: 207.11
• Mol File: 1644-88-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 208.4 °C at 760 mmHg
• Flash Point: 79.8 °C
• Appearance: /
• Density: 1.461 g/cm₃
• Vapor Pressure: 0.309mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-(Trifluoromethoxy)nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Trifluoromethoxy)nitrobenzene(1644-88-8)
• EPA Substance Registry System: 2-(Trifluoromethoxy)nitrobenzene(1644-88-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 1644-88-8(Hazardous Substances Data)

Usage

Uses

2-(Trifluoromethoxy)nitrobenzene is an impurity in the preparation of Riluzole (R510000).

InChI:InChI=1/C7H4F3NO3/c8-7(9,10)14-6-4-2-1-3-5(6)11(12)13/h1-4H

Upstream product

• 456-55-3 1-trifluoromethoxybenzene 
• 554-84-7 meta-nitrophenol 
• 7783-56-4 antimony(III) fluoride 
• 57830-55-4 2-((trifluoromethyl)sulfonyl)pyridine 
• 98-95-3 nitrobenzene 
• 927-84-4 bis(trifluoromethyl)peroxide 
• 175676-65-0 2-trifluoromethoxyphenylboronic acid 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 1261523-68-5 3-Amino-4-trifluoromethoxy-benzenesulfonamide 
• 1377582-59-6 3-Isothiocyanato-4-trifluoromethoxy-benzenesulfonamide 
• 1377582-60-9 3-thioureido-(4-trifluoromethoxy)benzenesulfonamide 

Relevant articles and documents

Process Development and Scale-up of the Continuous Flow Nitration of Trifluoromethoxybenzene

In this work, continuous flow nitration of trifluoromethoxybenzene (TFMB) was conducted in a microchannel reactor. The effects of process parameters, including temperature, residence time, sulfuric acid strength, flow rate, and reactor structure, were systemically investigated. It was found that the aforementioned process parameters had significant effect on TFMB conversion, while the product selectivity was merely sensitive to the reaction temperature. On the basis of the results of process parameter optimization, a scale-up strategy combining microreactor with distributed packed tubular reactor was presented. Consequently, excellent performance was achieved in the combined reactor with a kilogram-scale production.

Electrochemical Trifluoromethoxylation of (Hetero)aromatics with a Trifluoromethyl Source and Oxygen

Trifluoromethoxylated aromatics (ArOCF3) are valuable structural motifs in the area of drug discovery due to the enhancement of their desired physicochemical properties upon the introduction of the trifluoromethoxy group (CF3O). Although significant progress has been made recently in the introduction of CF3O group into aromatics, current methods either require the use of expensive trifluoromethoxylation reagents or require harsh reaction conditions. We present a conceptually new and operationally simple protocol for the direct C?H trifluoromethoxylation of (hetero)aromatics by the combination of the readily available trifluoromethylating reagent and oxygen under electrochemical reaction conditions. This reaction proceeds through the initial generation of CF3 radical followed by conversion to CF3O radical, addition to (hetero)aromatics and rearomatization. The utility of this electrochemical trifluoromethoxylation is illustrated by the direct incorporation of CF3O group into a variety of (hetero)aromatics as well as bio-relevant molecules.

NITRATION

The present invention relates to a process for preparing a nitrated compound, comprising the step of reacting a compound (A) comprising at least one substituted or unsubstituted aromatic or heteroaromatic ring, wherein said heteroaromatic ring comprises at least one heteroatom selected from the group consisting of oxygen, sulfur, phosphor, selenium and nitrogen, with a compound of formula (I) wherein Y is selected from the group consisting of hydrogen and nitro.