1737-06-0

Basic information

• Product Name: 4'-(TRIFLUOROMETHOXY)ACETANILIDE
• Synonyms: N1-[4-(TRIFLUOROMETHOXY)PHENYL]ACETAMIDE;4'-(TRIFLUOROMETHOXY)ACETANILIDE;4-(TRIFLUOROMETHOXY)ACETANILIDE;4'-(Trifluoromethoxy)acetanilide 97%;4'-(Trifluoromethoxy)acetanilide97%;N-(4-(trifluoroMethoxy)phenyl)acetaMide
• CAS NO: 1737-06-0
• Molecular Formula: C₉H₈F₃NO₂
• Molecular Weight: 219.16
• Mol File: 1737-06-0.mol

Chemical Properties

• Melting Point: 115-117°C
• Boiling Point: 296.8 °C at 760 mmHg
• Flash Point: 133.3 °C
• Appearance: /
• Density: 1.345 g/cm³
• Vapor Pressure: 0.00141mmHg at 25°C
• Refractive Index: 1.496
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.14±0.70(Predicted)
• CAS DataBase Reference: 4'-(TRIFLUOROMETHOXY)ACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-(TRIFLUOROMETHOXY)ACETANILIDE(1737-06-0)
• EPA Substance Registry System: 4'-(TRIFLUOROMETHOXY)ACETANILIDE(1737-06-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 1737-06-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4'-(Trifluoromethoxy)acetanilide is used as an intermediate in organic synthesis for the preparation of various organic compounds. Its unique structure allows for the formation of new chemical entities with potential applications in different fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4'-(Trifluoromethoxy)acetanilide is utilized for the preparation of various pharmaceutical drugs. Its presence in drug molecules can contribute to improved pharmacological properties, such as enhanced solubility, stability, and bioavailability.
Used as a Reagent in Chemical Reactions:
4'-(Trifluoromethoxy)acetanilide serves as a reagent in chemical reactions, facilitating the synthesis of complex organic molecules. Its reactivity and selectivity make it a valuable tool in the development of novel chemical processes.
Used as a Building Block for Synthesis of Other Organic Compounds:
4'-(TRIFLUOROMETHOXY)ACETANILIDE is also used as a building block for the synthesis of other organic compounds, enabling the creation of a diverse range of chemical structures with potential applications in various industries.
Used in Scientific Research:
4'-(Trifluoromethoxy)acetanilide has been studied for its potential biological and pharmacological activities, making it a valuable subject of scientific research. Its exploration in this context can lead to the discovery of new therapeutic agents and a deeper understanding of its properties and interactions.
Used in Industrial Applications:
4'-(TRIFLUOROMETHOXY)ACETANILIDE's versatility and importance in various scientific applications extend to industrial uses, where it can contribute to the development of new products and processes across different sectors.

InChI:InChI=1/C9H8F3NO2/c1-6(14)13-7-2-4-8(5-3-7)15-9(10,11)12/h2-5H,1H3,(H,13,14)

Upstream product

• 461-82-5 4-(trifluoromethoxy)aniline 
• 75-07-0 acetaldehyde 
• 75-36-5 acetyl chloride 
• 1265612-59-6 (E)-1-(4-(trifluoromethoxy)phenyl)ethan-1-one oxime 
• 42823-24-5 4-(trifluoromethoxy)aniline hydrochloride 
• 60-35-5 acetamide 
• 127-19-5 N,N-dimethyl acetamide 
• 100-65-2 N-Phenylhydroxylamine 
• 887144-94-7 Togni's reagent II 
• 1795-83-1 N-Phenylacetohydroxamic acid 
• 98-95-3 nitrobenzene 
• 874-90-8 4-methoxybenzonitrile 
• 100-07-2 4-methoxy-benzoyl chloride 
• 330-11-0 4-(trifluoromethoxy)benzoyl fluoride 

Downstream Products

• 2267-23-4 2-nitro-4-trifluoromethoxyaniline 
• 1025801-23-3 1-Azido-2-nitro-4-trifluoromethoxy-benzene 
• 658-89-9 4-(trifluoromethoxy)benzene-1,2-diamine 
• 877681-12-4 5-(trifluoromethoxy)-1,3-dihydro-2H-benzo[d]imidazol-2-one 
• 1351534-24-1 (2R)-2-[2-chloro-5-[[3-(6-methoxybenzisoxazol-3-yl)-2-oxo-5-trifluoromethoxybenzimidazol-1-yl]methyl]phenoxy]propanoic acid 
• 1351534-05-8 2-amino-4-trifluoromethoxy-N-acetylaniline 
• 142621-14-5 N-(4-trifluoromethoxyphenyl)-p-toluidine 
• 787-57-5 2-nitro-4-trifluoromethoxy-N-acetylaniline 
• 399-20-2 2-methyl-6-(trifluoromethoxy)benzo[d]thiazole 
• 256529-43-8 N-(2-chloro-4-(trifluoromethoxy)phenyl)acetamide 
• 175278-20-3 N-ethyl-4-(trifluoromethoxy)aniline 

Relevant articles and documents

Copper-promoted difunctionalization of unactivated alkenes with silanes

An efficient copper-catalyzed cascade difunctionalization of N-allyl anilines toward the synthesis of silylated indolines using commercially available silanes has been reported. This strategy provides a new avenue for the synthesis of a diverse array of i

Dehydrative Beckmann rearrangement and the following cascade reactions

The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.

An Environmentally Benign, Catalyst-Free N?C Bond Cleavage/Formation of Primary, Secondary, and Tertiary Unactivated Amides

Herein, we report an operationally simple, cheap, and catalyst-free method for the transamidation of a diverse range of unactivated amides furnishing the desired products in excellent yields. This protocol is environmentally friendly and operates under extremely mild conditions without using any promoter or additives. Significantly, this strategy has been implied in the chemoselective synthesis of a pharmaceutical molecule, paracetamol, on a gram-scale with excellent yield. We anticipate that this universally applicable strategy will be of great interest in drug discovery, biochemistry, and organic synthesis.

Synthesis and antileishmanial activity of fluorinated rhodacyanine analogues: The ‘fluorine-walk’ analysis

In a search for potent antileishmanial drug candidates, eighteen rhodacyanine analogues bearing fluorine or perfluoroalkyl substituents at various positions were synthesized. These compounds were tested for their inhibitory activities against Leishmania martiniquensis and L. orientalis. This ‘fluorine-walk’ analysis revealed that the introduction of fluorine atom at C-5, 6, 5′, or 6′ on the benzothiazole units led to significant enhancement of the activity, correlating with the less negative reduction potentials of the fluorinated analogues confirmed by the electrochemical study. On the other hand, [sbnd]CF3 and [sbnd]OCF3 groups were found to have detrimental effects, which agreed with the poor aqueous solubility predicted by the in silico ADMET analysis. In addition, some of the analogues including the difluorinated species showed exceptional potency against the promastigote and axenic amastigote stages (IC50 = 40–85 nM), with the activities surpassing both amphotericin B and miltefosine.

TRIFLUOROMETHOXYLATION OF ARENES VIA INTRAMOLECULAR TRIFLUOROMETHOXY GROUP MIGRATION

The present invention provides a process of producing a trifluoromethoxylated aryl or trifluoromethoxylated heteroaryl having the structure: (I), wherein A is an aryl or heteroaryl, each with or without subsutitution; and R1 is -H, -(alkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), - (alkylaryl), - (alkylheteroaryl), -NH-(alkyl), -N(alkyl)2, -NH-(alkenyl), -NH-(alkynyl) -NH-(aryl), -NH-(heteroaryl), -O-(alkyl), -O-(alkenyl), -O-(alkynyl), -O-(aryl), -O-(heteroaryl), -S-(alkyl), -S- (alkenyl), -S-(alkynyl), -S-(aryl), or -S-(heteroaryl), comprising: (a) reacting a compound having the structure: (II), with a trifluoromethylating agent in the presence of a base in a first suitable solvent under conditions to produce a compound having the structure: (III); and (b) maintaining the compound produced in step (a) in a second suitable solvent under conditions sufficient to produce the trifluoromethoxylated aryl or trifluormethoxylated heteroaryl having the structure: (I).

Mechanistic studies on intramolecular C-H trifluoromethoxylation of (hetero)arenes via OCF3-migration

The one-pot two-step intramolecular aryl and heteroaryl C-H trifluoromethoxylation recently reported by our group has provided a general, scalable, and operationally simple approach to access a wide range of unprecedented and valuable OCF3-containing building blocks. Herein we describe our investigations to elucidate its reaction mechanism. Experimental data indicate that the O-trifluoromethylation of N-(hetero)aryl-N-hydroxylamine derivatives is a radical process, whereas the OCF3-migration step proceeds via a heterolytic cleavage of the N-OCF3 bond followed by rapid recombination of a short-lived ion pair. Computational studies further support the proposed ion pair reaction pathway for the OCF3-migration process. We hope that the current study would provide useful insights for the development of new transformations using versatile N-(hetero)aryl-N-hydroxylamine synthons.

Highly efficient dehydrogenative cross-coupling of aldehydes with amines and alcohols

A common protocol for the synthesis of amides, esters and α-ketoesters via cross dehydrogenative coupling of aldehydes and amines/alcohols has been developed. The method is applicable to a wide variety of alcohols and amines as well as aliphatic and aromatic aldehydes. Also, the use of acetaldehyde for acetylation and ethyl glyoxalate to access 2-oxo-amino esters is presented for the first time.

Sulphuric acid immobilized on silica gel (H2SO4-SiO2) as an eco-friendly catalyst for transamidation

A novel method of transamidation of carboxamides with amines by using catalytic amounts of H2SO4-SiO2 has been developed under solvent free conditions. The transamidation is compatible with a wide range of aromatic, heteroaromatic, aliphatic, cyclic/acyclic primary or secondary amines. The metal/solvent-free conditions represent a significant improvement over other existing methods as the reaction can be performed in open air conditions and no column purification is required. The versatility of this methodology was further demonstrated by synthesizing the commercially available drug procainamide.

Pd-Catalyzed C-H activation/oxidative cyclization of acetanilide with norbornene: Concise access to functionalized indolines

An efficient Pd-catalyzed oxidative cyclization reaction for the synthesis of functionalized indolines by direct C-H activation of acetanilide has been developed. The norbornylpalladium species formed via direct ortho C-H activation of acetanilides is supposed to be a key intermediate in this transformation. This journal is the Partner Organisations 2014.

Trifluoromethoxylation of arenes: Synthesis of ortho- Trifluoromethoxylated aniline derivatives by OCF3 migration

Aryl trifluoromethoxylation by a two-step sequence of O-trifluoromethylation of N-aryl-N-hydroxylamine derivatives and intramolecular OCF3 migration is presented. This protocol allows easy access to a wide range of synthetically useful ortho-OCF3 aniline derivatives. In addition, it utilizes bench-stable reagents, is operationally simple, shows high functional-group tolerance, and is amenable to gram-scale as well as one-pot synthesis.Areaction mechanism of a heterolytic cleavage of the N-OCF3 bond followed by recombination of the resulting nitrenium ion and trifluoromethoxide is proposed for the OCF3-migration reaction.