404-27-3

Basic information

• Product Name: 2,2,2-Trifluoro-4'-nitroacetanilide
• Synonyms: 2,2,2-Trifluoro-4'-nitroacetanilide;2,2,2-Trifluoro-N-(4-nitrophenyl)acetaMide
• CAS NO: 404-27-3
• Molecular Formula: C₈H₅F₃N₂O₃
• Molecular Weight: 234.13
• Product Categories: Amines;Aromatics
• Mol File: 404-27-3.mol

Chemical Properties

• Melting Point: 149-150°C
• Appearance: /
• CAS DataBase Reference: 2,2,2-Trifluoro-4'-nitroacetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-Trifluoro-4'-nitroacetanilide(404-27-3)
• EPA Substance Registry System: 2,2,2-Trifluoro-4'-nitroacetanilide(404-27-3)

Safety Data

• Hazardous Substances Data: 404-27-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,2,2-Trifluoro-4'-nitroacetanilide is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure, featuring a trifluoromethyl group and a nitro group, makes it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2,2-Trifluoro-4'-nitroacetanilide is used as a key intermediate in the synthesis of certain drugs. Its presence in the molecular structure can impart specific properties, such as increased lipophilicity or metabolic stability, which are desirable for drug candidates.
Used in Agrochemical Industry:
2,2,2-Trifluoro-4'-nitroacetanilide also finds applications in the agrochemical industry, where it serves as a precursor for the development of new pesticides or herbicides. Its unique structural features can contribute to the enhanced performance and selectivity of these agrochemicals.

Upstream product

• 100-01-6 4-nitro-aniline 
• 407-25-0 trifluoroacetic anhydride 
• 404-24-0 2,2,2-trifluoro-N-phenylacetamide 
• 2733-41-7 4-nitrobenzoyl azide 
• 76-05-1 trifluoroacetic acid 
• 183266-61-7 1-(trifluoroacetyl)benzotriazole 
• 51599-76-9 N-trifluoroacetoxy succinimide 
• 62-53-3 aniline 
• 1492828-74-6 methyl 2,2,2-trifluoro-N-(p-nitrophenyl)acetimidate 
• 145372-31-2 N-(4-nitrophenyl)-2,2,2-trifluoroacetimidoyl chloride 
• 1228956-92-0 C₁₄H₁₄N₄O₂ 
• 636-98-6 p-nitrobenzene iodide 
• 354-38-1 2,2,2-trifluoroacetamide 
• 27691-52-7 S,S-dimethyl-N-(p-nitrophenyl)sulfilimine 

Downstream Products

• 100-01-6 4-nitro-aniline 
• 62-53-3 aniline 
• 76-05-1 trifluoroacetic acid 
• 1830-44-0 (2-amino-5-nitro-phenyl)-pyridin-2-yl-methanone 
• 75-89-8 2,2,2-trifluoroethanol 
• 79692-35-6 Hexadecanoic acid (4-diethylamino-1-methyl-butyl)-[4-(3-{4-[(4-diethylamino-1-methyl-butyl)-hexadecanoyl-amino]-phenyl}-ureido)-phenyl]-amide 
• 344747-21-3 Hexadecanoic acid (4-diethylamino-1-methyl-butyl)-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-amide 
• 79692-45-8 Hexadecanoic acid (4-amino-phenyl)-(4-diethylamino-1-methyl-butyl)-amide 
• 79692-50-5 N-[4-(4-Diethylamino-1-methyl-butylamino)-phenyl]-2,2,2-trifluoro-acetamide 
• 100-15-2 N-methyl(p-nitroaniline) 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 53446-90-5 N-(4-Amino-phenyl)-2,2,2-trifluoro-acetamide 

Relevant articles and documents

The reaction of 4-substituted aryl isocyanates with NaBH4/trifluoroacetic acid (TFA)

Treatment of 4-substituted aryl isocyanates (cf. 2a-f) with NaBH4/TFA leads to the corresponding 4-substituted N,N-bis(2,2,2-trifluoroethyl)aniline derivatives (3a-d) in excellent yield except where an electron-withdrawing group is present (cf.

Surface modification of polymers with bis(arylcarbene)s from bis(aryldiazomethane)s: preparation, dyeing and characterization

Modification of polymer beads by bis(arylcarbene) insertion provides access to materials with similar bulk properties, but different surface chemical characteristics, compared to the unmodified polymer. A subsequent dyeing process using different diazonium salts generates colored polymers with a variety of surface functional groups. XPS and solid state NMR spectra were used to characterize modified and dyed polymers, which showed this protocol was both successful and general. BET data showed that the surface area changed significantly after modification, while BJH data showed pore size distribution was unchanged. TG/DSC analysis and Elemental Analysis were also used to characterize modified polymers. This permitted calculation and comparison of the loadings of surface area and the modification effects with different chemical structure of bis(arylcarbene)s. This work shows that the bis(arylcarbene) system is as effective as mono(arylcarbene)s, but of significance since the starting bis(aryldiazomethane)s are more easily accessible and easier to handle than the mono(aryldiazomethane)s. All this data indicates that the surface property of polymers is modified.

Carbon-Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)-CF3 Bond Cleavage

The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF3 group with various alkyl or aryl groups is described. A variety of aryl, quinolin-8-yl, and (hetero)alkyl functional groups as well as F, Cl, and Br atoms are well tolerated. These moisture-stable and easily available trifluoroacetyl amides can be conveniently obtained and used as new versatile precursors for isocyanates. The control experiments show that the reaction proceeds via an isocyanate intermediate and/or alkoxide/amide dual anionic intermediate.

Removal of some common glycosylation by-products during reaction work-up

With the aim of improving the general glycosylation protocol to facilitate easy product isolation it was shown that amide by-products from glycosylation with trichloroacetimidate and N-phenyl trifluoroacetimidate donors could be removed during reaction work-up by washing with a basic aqueous solution. Excess glycosyl acceptor or lactol originating from glycosyl donor hydrolysis could equally be removed from the reaction mixture by derivatization with a basic tag and washing with an acidic solution during reaction work-up.

Regioselective ortho-nitration of N-phenyl carboxamides and primary anilines using bismuth nitrate/acetic anhydride

An efficient and one-pot synthetic method for the regioselective ortho-nitration of the N-phenyl carboxamides and primary anilines has been developed by using bismuth nitrate and acetic anhydride as the nitrating reagents. Reaction proceeds at room temperature and results in corresponding ortho-nitrated products in moderate to excellent yields. This method provides an operationally simple, regioselective, and efficient access to synthesize o-nitro anilines under the mild conditions.

The development of N-aryl trifluoroacetimidate-based benzyl and allyl protecting group reagents

An exploration of the role of para-substituents on the balance between stability and reactivity of N-phenyl trifluoroacetimidates prompted the discovery of new reagents for the addition of allyl and benzyl protecting groups, namely O-allyl and O-benzyl N-

The reaction of 2-arylazo-1-vinylpyrroles with trifluoroacetic anhydride: Unexpected formation of N-aryl-2,2,2-trifluoroacetamides and conjugated polymers

2-Arylazo-1-vinylpyrroles under the action of trifluoroacetic anhydride (CH2Cl2 or benzene, -5-0 °C, 1 h) form N-aryl-2,2,2-trifluoroacetamides along with conjugated (electroconducting and paramagnetic) polymers.

A simple and efficient method for trifluoroacetylation of arylamines using trifluoroacetic acid and triphosgene

A simple and efficient one-pot procedure for trifluoroacetylation of arylamines using trifluoroacetic acid and triphosgene is reported. A mixed trifluoroacetic anhydride generated in situ reacts with a variety of arylamines to give the corresponding trifluroacetamides in high yields.

Trifluoroacetylation of amines with trifluoroacetic acid in the presence of trichloroacetonitrile and triphenylphosphine

We developed a mild and convenient trifluoroacetylation process for amines using a combination of trichloroacetonitrile and triphenylphosphine. The reaction that we designed is applicable to the trifluoroacetylation of a wide variety of amines, including amines with stereogenic centers, which underwent trifluoroacetylation without racemization.

A one-pot procedure for trifluoroacetylation of arylamines using trifluoroacetic acid as a trifluoroacetylating reagent

A convenient procedure for the preparation of aryl trifluoroacetamides from aryl amines is described that employs 2-4 M equiv of trifluoroacetic acid in refluxing xylene as a trifluoroacetylating agent. Addition of an amount of pyridine that is equimolar to the amount of trifluoroacetic acid present in the reaction mixture facilitates the trifluoroacetylation of rather basic arylamines.