Acetamide, 2,2,2-trifluoro-N-(2-nitrophenyl)-

Base Information

• Chemical Name: Acetamide, 2,2,2-trifluoro-N-(2-nitrophenyl)-
• CAS No.: 2727-72-2
• Molecular Formula: C8H5F3N2O3
• Molecular Weight: 234.135
• Mol file: 2727-72-2.mol

Synonyms:2-nitrotrifluoroacetanilide;2-Nitrophenyl-trifluoracetamid;o-Nitrophenyltrifluoracetamid;2'-Nitro-2,2,2-trifluoracetanilid;

Chemical Property of Acetamide, 2,2,2-trifluoro-N-(2-nitrophenyl)-

Chemical Property:

• PSA: 74.92000
• LogP: 2.69180

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Acetamide, 2,2,2-trifluoro-N-(2-nitrophenyl)- (also known as o-nitrotrifluoroacetanilide) serves as a key intermediate in the synthesis of N-alkyl o-phenylenediamines, which are valuable precursors for isoalloxazines (flavins) and other pharmaceutical applications. Its trifluoroacetyl group enhances reactivity compared to traditional acetamide derivatives, facilitating efficient alkylation and hydrolysis in a one-pot phase transfer process. Acetamide, 2,2,2-trifluoro-N-(2-nitrophenyl)-'s utility lies in its role as a starting material for streamlined, high-yield transformations under mild conditions, offering advantages over conventional methods.

Technology Process of Acetamide, 2,2,2-trifluoro-N-(2-nitrophenyl)-

There total 9 articles about Acetamide, 2,2,2-trifluoro-N-(2-nitrophenyl)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

aniline (62-53-3) + trifluoroacetic anhydride (407-25-0) → 2,2,2-trifluoro-N-(2-nitrophenyl)acetamide (2727-72-2)

Guidance literature:

With ammonium nitrate; In chloroform; at 25 ℃; for 0.5h;

DOI:10.1021/jo00328a013

Reference yield: 81.0%

2-nitro-aniline (88-74-4) + trifluoroacetic anhydride (407-25-0) → 2,2,2-trifluoro-N-(2-nitrophenyl)acetamide (2727-72-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 28 ℃; for 3h;

Reference yield: 80.0%

2-nitro-aniline (88-74-4) + trifluoroacetic acid (76-05-1) → 2,2,2-trifluoro-N-(2-nitrophenyl)acetamide (2727-72-2)

Guidance literature:

With triethylamine; trichloroacetonitrile; triphenylphosphine; In acetonitrile; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.11.105

upstream raw materials:

aniline

trifluoroacetic anhydride

2,2,2-trifluoro-N-phenylacetamide

2-nitro-aniline

Downstream raw materials:

2-nitro-aniline

Refernces

A 'one-pot' phase transfer alkylation/hydrolysis of o-nitrotrifluoroacetanilides. A convenient route to N-alkyl o-phenylenediamines

10.1080/00397919608003827

The research explores a novel synthetic method for producing N-alkyl o-phenylenediamines through a one-pot phase transfer alkylation and hydrolysis process. The study aims to develop a simple and efficient route for synthesizing these compounds, which are important intermediates in the preparation of isoalloxazines (flavins) and have potential applications in various chemical and pharmaceutical fields. The key chemicals used in this research include o-nitrotrifluoroacetanilides as the starting materials, dimethylsulfate, benzyl bromide, and 1-bromopropane as electrophiles, and tetrabutylammonium chloride or benzyltriethylammonium chloride as phase transfer catalysts. The process involves a one-pot reaction where the o-nitrotrifluoroacetanilides undergo alkylation followed by hydrolysis under phase transfer conditions, yielding N-alkyl o-nitroanilines in good to excellent yields. The study concludes that this method is superior to previous methods involving o-nitroacetanilides due to the increased reactivity and ease of preparation of the trifluoroacetanilides. The findings suggest that this one-pot synthesis provides a convenient and operationally simple approach for the preparation of N-alkyl o-phenylenediamines, which can be further reduced to the desired products.

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