17474-05-4

Basic information

• Product Name: 2,6-dinitro-N-phenyl-4-(trifluoromethyl)aniline
• CAS NO: 17474-05-4
• Molecular Formula: C₁₃H₈F₃N₃O₄
• Molecular Weight: 327.2155
• Mol File: 17474-05-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 358.6°C at 760 mmHg
• Flash Point: 170.7°C
• Density: 1.538g/cm³
• Vapor Pressure: 2.52E-05mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: 2,6-dinitro-N-phenyl-4-(trifluoromethyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dinitro-N-phenyl-4-(trifluoromethyl)aniline(17474-05-4)
• EPA Substance Registry System: 2,6-dinitro-N-phenyl-4-(trifluoromethyl)aniline(17474-05-4)

Safety Data

• Hazardous Substances Data: 17474-05-4(Hazardous Substances Data)

Usage

Use

Synthetic intermediate in pharmaceuticals, agricultural chemicals, and dyes production

Physical Characteristics

Pale yellow solid

Thermal Stability

High

Solubility in Water

Low

Chemical Nature

Nitroaromatic compound

Hazards

Considered hazardous to human health and the environment

Handling and Disposal

Requires careful handling and disposal

Upstream product

• 393-75-9 4-chloro-3,5-dinitrobenzotrifluoride 
• 62-53-3 aniline 

Relevant articles and documents

Solvent and substituent effects on the reaction of 2- and 4-chloro-3,5-dinitrobenzotrifluorides with substituted anilines

The solvent effect on a nucleophilic substitution reaction of 2- and 4-chloro-3,5- dinitrobenzotrifluoride with substituted anilines was studied in methanol, acetonitrile, and toluene at 25°C. This reaction is of second order, except 2-chloro-3,5-dinitrobenzotrifluoride in toluene shows third order. The kA values are found to be dependent on the substituent in aniline and give good Hammett correlations. The obtained ρ values are -4.07 and -4.62, for the reaction of anilines with 2-chloro-3,5- dinitrobenzotrifluoride in methanol and acetonitrile, respectively. The ρ values for the reaction of the anilines with 4-chloro-3,5- dinitrobenzotrifluoride are-3.38,-4.11, and-4.34 in methanol, acetonitrile, and toluene, respectively. The reaction of the former compound with anilines in toluene shows a second order in aniline. The dependence of the reaction on the external base such as DABCO suggests a proton transfer controlling step.

Synthesis and evaluation of dinitroanilines for treatment of cryptosporidiosis

The efficacy of a series of dinitroaniline herbicide derivatives for the treatment of Cryptosporidium parvum infections has been studied. The lead compounds oryzalin (compound 1) and trifluralin (compound 2) have low water solubility (3 ppm) which was alleged to be a major contributor to their poor pharmacokinetic availability. Derivatives of compounds 1 and 2 were synthesized. In these derivatives the functionality at the C-1 amine position or the C-4 position was substituted with groups with various hydrophilicities to determine if a direct relation existed between water solubility and overall activity. The chlorinated precursors of these derivatives were also examined and were found to be less active in the C. parvum assays, a result in direct contrast to earlier work with Leishmania. Enhanced water solubility alone did not overcome the drug availability problem; however, several candidates with similar activities but with toxicities lower than those of the lead compounds were produced.

Benzimidazole compounds

The present patent application discloses compounds having the formula STR1 or a pharmaceutically acceptable salt thereof wherein R 3, R 4, R 6 and R 7 each have the meanings set forth in the specification.The compounds are useful for the treatment of various central nervous system disorders such as epilepsy and other convulsive disorders, anxiety, sleep disorders and memory disorders.