384-22-5

Usage

Chemical Properties

white to light yellow crystal powder

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 2346, 1947 DOI: 10.1021/ja01202a028Synthesis, p. 932, 1980 DOI: 10.1055/s-1980-29276

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A halogenated aromatic nitro compound. Aromatic nitro compounds range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups.

Fire Hazard

2-Nitrobenzotrifluoride is combustible.

InChI:InChI=1/C6H5F9/c1-2-3(7,8)4(9,10)5(11,12)6(13,14)15/h2H2,1H3

Upstream product

• 109-95-5 ethyl nitrite 
• 64-17-5 ethanol 
• 386-71-0 2-nitro-3-(trifluoromethyl)aniline 
• 393-11-3 4-nitro-3-(trifluoromethyl)benzeneamine 
• 75-61-6 dibromodifluoromethane 
• 577-19-5 2-nitrophenyl bromide 
• 609-73-4 o-nitroiodobenzene 
• 1514-87-0 metyhyl chlorodifluoroacetate 
• 98-08-8 α,α,α-trifluorotoluene 
• 75-63-8 Bromotrifluoromethane 
• 98-95-3 nitrobenzene 
• 76-05-1 trifluoroacetic acid 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 88-73-3 2-Chloronitrobenzene 

Downstream Products

• 124233-23-4 9-(4-nitro-3-trifluoromethylphenyl)-fluorene 
• 89303-28-6 4-Benzenesulfonylmethyl-1-nitro-2-trifluoromethyl-benzene 
• 89303-34-4 1-Benzenesulfonylmethyl-2-nitro-3-trifluoromethyl-benzene 
• 39055-80-6 3-trifluoromethyl-salicylonitrile 
• 393-11-3 4-nitro-3-(trifluoromethyl)benzeneamine 
• 393-39-5 4-fluoro-2-(trifluoromethyl)aniline 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 10092-39-4 N,N'-Bis<2-(trifluoromethyl)phenyl>urea 
• 386-72-1 2-nitro-3-(trifluoromethyl)phenol 
• 88-30-2 3-trifluoromethyl-4-nitrophenol 
• 386-71-0 2-nitro-3-(trifluoromethyl)aniline 
• 172217-02-6 7-(trifluoromethyl)indole 
• 486-25-9 9-fluorenone 
• 93742-93-9 (±)-methyl 2-[4-nitro-3-(trifluoromethyl)phenyl]propanoate 

Relevant academic research and scientific papers

Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent

The trifluoromethylation of iodoarenes was accomplished by use of a 2-trifluoromethylbenzimidazoline derivative as the trifluoromethylating reagent and a catalytic amount of Cu(I) in the presence of 2,2'-bipyridyl as the ligand. Through a mechanistic study, we found that the oxidative addition of the iodoarene to the Cu(I)–CF3 species is the rate-determining step.

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

Au@ZnO Core-Shell: Scalable Photocatalytic Trifluoromethylation Using CF3CO2Na as an Inexpensive Reagent under Visible Light Irradiation

Trifluoromethylation is of significant importance for the synthesis of many small molecules vital for medicinal and agrochemical research. The importance of the CF3 group as well as the related synthetic challenges is so evident that many reagents have been reported for the synthesis of trifluoromethylated compounds, but these typical reagents are expensive and the methods for preparing them are difficult. Here, we report a new scalable and operationally simple trifluoromethylation reaction using sodium trifluoroacetate as a reagent and Au-modified ZnO as a photocatalyst under visible light irradiation. The reaction proceeds via trifluoromethylation of a broad range of aryl halides, arylboronic acids, and arene and heteroarene substrates. Some pharmaceutical and agrochemical compounds have been trifluoromethylated directly to demonstrate the applicability of the method.

Preparation method of substituted nitrobenzene compound

The invention discloses a preparation method of a substituted nitrobenzene compound. The method comprises the following steps: carrying out a decarboxylation reaction as shown below on a compound II under the action of alkali in a solvent at the temperature of 150 to 250 DEG C to obtain a compound I; the alkali is one or more of carbonates and bicarbonates of alkali metals. Compared with some metal-catalyzed decarboxylation methods, the preparation method of the substituted nitrobenzene compound has the advantages of simple operation, low production cost, convenient post-treatment and high yield, and more application values in industrial production.

Ligand-free trifluoromethylation of iodoarenes by use of 2-Aryl-2-trifluoromethylbenzimidazoline as new trifluoromethylating reagent

N-Methyl 2-aryl-2-trifluoromethylbenzimidazolines were synthesized and utilized in the trifluoromethylation reaction of iodoarenes in the presence of copper(I) salt and base. Iodoarenes bearing electron-donating and electron-withdrawing groups were tolerant to this reaction in the absence of a ligand and gave trifluorotoluene derivatives in good to high yields.

Nucleophilic trifluoromethylation of electron-deficient arenes

A novel trifluoromethylation of arenes is presented, which proceeds under mild reaction conditions and has the potential for late-stage functionalisation of pharmaceuticals and agrochemicals. The new reaction allows for the regioselective conversion of nitroarenes into 1,2-trifluoromethylated nitroarenes, via a C-H activation pathway. Furthermore, a substitution of nitroarenes to trifluoromethyl arenes is also presented.

Copper-catalysed synthesis of trifluoromethyl(hetero)arenes from di(hetero)aryl-λ3-iodanes

An efficient synthesis of trifluoromethylated (hetero)arenes has been achieved through the regioselective copper-catalyzed trifluoromethylation of di(hetero)aryl-λ3-iodanes, employing readily available trifluoromethyltrimethylsilane. The reaction works well for both symmetrical and unsymmetrical di(hetero)aryl-λ3-iodanes with good regioselectivity and also tolerates diverse functional groups such as bromo, iodo, cyano, nitro, ester, ketone and enolizable ketone.

DBU-Promoted Trifluoromethylation of Aryl Iodides with Difluoromethyltriphenylphosphonium Bromide

DBU-promoted trifluoromethylation of aryl iodides with difluoromethyltriphenylphosphonium bromide (DFPB) in the presence of copper source is described. In this transformation, DBU not only acts as base to deprotonate the difluoromethyl group in DFPB to generate difluoromethylene phosphonium ylide Ph3P+CF2-, but also converts the difluorocarbene generated from ylide Ph3P+CF2- into trifluoromethyl anion, finally resulting in the trifluoromethylation of aryl iodides. The reactions proceeded smoothly to afford expected products in moderate to good yields.

Trifluoromethylation of haloarenes with a new trifluoro-methylating reagent Cu(O2CCF2SO2F)2

A new trifluoromethylating reagent Cu(O2CCF2SO2F)2, which easily decomposes to generate active CuCF3 species in DMF at room temperature, has been conveniently prepared from inexpensive starting materials on a large scale. This new reagent can be applied to efficiently trifluoromethylate a variety of haloarenes under mild conditions, providing good-to-excellent yields of the desired products.