62476-58-8 | 3-Amino-2-chlorobenzotrifluoride

CAS:62476-58-8 | 3-Amino-2-chlorobenzotrifluoride,Description

2-Chloro-3-(trifluoromethyl)aniline is a chemical compound with the molecular formula C7H5ClF3N. It has a molecular weight of 195.57. It is a pale-purple to purple solid or liquid.

Synthesis Analysis

A method for synthesizing 2-methyl-3-trifluoromethyl aniline has been disclosed, which takes 2-chloro-3-trifluoromethyl aniline as a raw material. The synthetic route involves introducing methylthio on the 2-chloro-3-trifluoromethyl aniline, reacting with sulfonyl chloride to convert the methylthio into chloromethyl, and then neutralizing and hydrogenating to obtain pure 2-methyl-3-trifluoromethyl aniline.

Molecular Structure Analysis

The molecular structure of 2-Chloro-3-(trifluoromethyl)aniline consists of a benzene ring with a chlorine atom and a trifluoromethyl group attached to it, along with an amine group.

Chemical Reactions Analysis

While specific chemical reactions involving 2-Chloro-3-(trifluoromethyl)aniline are not available, anilines in general are known for their high and unselective reactivity, which has prevented their incorporation into many interesting transformations, such as the functionalization of alkenes.

Physical And Chemical Properties Analysis

2-Chloro-3-(trifluoromethyl)aniline is a pale-purple to purple solid or liquid. It should be stored in a dark place, under an inert atmosphere, at room temperature.

Scientific Research Applications

1. Trifluoromethylarylation of Alkenes

• Application Summary: This compound is used in the trifluoromethylarylation of alkenes. This process involves the functionalization of alkenes, which are versatile substrates that offer great potential for diversification using a plethora of established reactions.
• Methods of Application: The method allows the trifluoromethylarylation of alkenes using anilines, for the first time, with no need for additives, transition metals, photocatalysts or an excess of reagents. An in-depth mechanistic study reveals the key role of hexafluoroisopropanol (HFIP) as a unique solvent, establishing a hydrogen bonding network with aniline and trifluoromethyl reagent.
• Results or Outcomes: This work uncovers a new mode of reactivity that involves the use of abundant anilines as a non-prefunctionalized aromatic source and the simultaneous activation of trifluoromethyl hypervalent iodine reagent.

2. FDA-Approved Trifluoromethyl Group-Containing Drugs

• Application Summary: 2-Chloro-3-(trifluoromethyl)aniline is found in FDA-approved drugs. It is incorporated into potential drug molecules, including their syntheses and uses for various diseases and disorders.
• Results or Outcomes: The review covers the detailed chemistry of 19 FDA-approved drugs in the past 20 years, which contains the trifluoromethyl group as one of the pharmacophores.

3. Synthesis of 2-Methyl-3-Trifluoromethyl Aniline

• Application Summary: 2-Methyl-3-Trifluoromethyl Aniline is an important intermediate of medicine and pesticide. It is mainly used for synthesizing analgesic and herbicide, veterinary anti-inflammatory drug and the like.
• Methods of Application: The specific methods of application or experimental procedures are not detailed in the source.
• Results or Outcomes: The compound is a key intermediate for synthesizing flunixin meglumine.

4. Synthesis of 2-Amino-5-chlorobenzotrifluoride

• Application Summary: 4-Chloro-2-(trifluoromethyl)aniline is used in the synthesis of 2-amino-5-chloro 3-(trifluoromethyl)benzenethiol.
• Methods of Application: The specific methods of application or experimental procedures are not detailed in the source.
• Results or Outcomes: The compound is used in the synthesis of 2-amino-5-chloro 3-(trifluoromethyl)benzenethiol.

5. Synthesis of 2-Methyl-3-Trifluoromethyl Aniline

• Application Summary: 2-Methyl-3-Trifluoromethyl Aniline is an important intermediate of medicine and pesticide. It is mainly used for synthesizing analgesic and herbicide, veterinary anti-inflammatory drug and the like.
• Methods of Application: The specific methods of application or experimental procedures are not detailed in the source.
• Results or Outcomes: The compound is a key intermediate for synthesizing flunixin meglumine.

6. Synthesis of 2-Amino-5-chlorobenzotrifluoride

• Application Summary: 4-Chloro-2-(trifluoromethyl)aniline is used in the synthesis of 2-amino-5-chloro 3-(trifluoromethyl)benzenethiol.
• Methods of Application: The specific methods of application or experimental procedures are not detailed in the source.
• Results or Outcomes: The compound is used in the synthesis of 2-amino-5-chloro 3-(trifluoromethyl)benzenethiol.

Safety And Hazards

This chemical is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It causes skin irritation, serious eye irritation, and is harmful if swallowed, in contact with skin, or if inhaled.

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