321182-37-0

Basic information

• Product Name: 2,4,5-TRIFLUORO-1,3-PHENYLENEDIAMINE
• Synonyms: 1,3-DIAMINO-2,4,5-TRIFLUOROBENZENE;2,4,5-TRIFLUORO-1,3-PHENYLENEDIAMINE;1,3-Benzenediamine,2,4,5-trifluoro-(9CI)
• CAS NO: 321182-37-0
• Molecular Formula: C6H5F3N2
• Molecular Weight: 162.11
• Product Categories: HALIDE
• Mol File: 321182-37-0.mol

Chemical Properties

• Melting Point: 74.0 to 77.0 °C
• Boiling Point: 244.8°C at 760 mmHg
• Flash Point: 107.1°C
• Appearance: /
• Density: 1.52g/cm³
• Vapor Pressure: 0.0298mmHg at 25°C
• Refractive Index: 1.564
• Solubility: soluble in Methanol
• CAS DataBase Reference: 2,4,5-TRIFLUORO-1,3-PHENYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-TRIFLUORO-1,3-PHENYLENEDIAMINE(321182-37-0)
• EPA Substance Registry System: 2,4,5-TRIFLUORO-1,3-PHENYLENEDIAMINE(321182-37-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 321182-37-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Industry:
2,4,5-TRIFLUORO-1,3-PHENYLENEDIAMINE is used as an intermediate for the synthesis of various dyes and pigments, contributing to the development of a wide range of colorants for different applications.
Used in Pharmaceutical Industry:
2,4,5-TRIFLUORO-1,3-PHENYLENEDIAMINE is used as an intermediate in the production of pharmaceuticals, playing a crucial role in the synthesis of certain medicinal compounds.
Used as an Oxidizing Agent in Organic Synthesis:
2,4,5-TRIFLUORO-1,3-PHENYLENEDIAMINE is employed as an oxidizing agent in organic synthesis, facilitating various chemical reactions due to its strong oxidizing properties.
However, it is important to note that the use of 2,4,5-TRIFLUORO-1,3-PHENYLENEDIAMINE in consumer products and broader industrial applications is restricted due to its potential hazards to human health and the environment. Its production, handling, and disposal are subject to strict regulations to mitigate its environmental and health impacts.

InChI:InChI=1/C6H5F3N2/c7-2-1-3(10)5(9)6(11)4(2)8/h1H,10-11H2

Upstream product

• 344-07-0 1-chloro-2,3,4,5,6-pentafluorobenzene 
• 359786-37-1 4-chloro-2,5,6-trifluoro-1,3-phenylenediamine 
• 363-72-4 Pentafluorobenzene 
• 392-56-3 Hexafluorobenzene 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 1198-63-6 2,4,5,6-tetrafluorobenzene-1,3-diamine 

Relevant articles and documents

Amino- and hydrodefluorination of polyfluoroaromatic amines with aqueous ammonia in a steel autoclave. Synthesis of highly pure tetrafluorophenylenediamines

The action of aqueous ammonia on liexafhiorobenzene in a steel autoclave at 180-220 °C yields a mixture of isomeric tet rafluorophenylenediamines and 2,4,5-trifhioroplienylene-1,3-diamine. The content of the hydrodefluorination product significantly depends on the reaction temperature and time. Tetrafluorophenylene-1,3-diamine undergoes hydrodefluorination with aqueous ammonia in a steel autoclave at 200 °C to give 2,4,5-trifluorophenylene-1,3- diamine; when the additives of NH4F and/or FeCl3 are present, 2,5-difluorophenylene-1,3-diamine is additionally formed. The hydrodefluorination products are not formed during bis-aminodefluorination of hexafluorobenzene with aqueous ammonia in a glass reactor or with anhydrous ammonia (in a mixture with aprotic solvent) in a steel autoclave.

Selective mono-and diamination of polyfluorinated benzenes and pyridines with liquid ammonia

Amination of pentafluoropyridine, 2,3,5,6-tetrafluoropyridine, 4-chlorotetrafluoropyridine, 3,5-dichlorotrifluoropyridine, octafluorotoluene, α,α,α,2,3,5,6-heptafluorotoluene, decafluoro-m-xylene, decafluorobiphenyl, hexafluorobenzene, and pentafluorobenzene with liquid ammonia was investigated. Bis-aminodefluorination temperatures for the majority of substrates were shown to exceed significantly the corresponding temperatures of monoaminodefluorination. The optimal conditions for selective preparation of mono-and diaminopolyfluoro(het)arenes were elucidated. An efficient method for isolation of particular polyfluorophenylenediamines from product mixtures formed in nonselective reactions of pentafluorobenzene and hexafluorobenzene with aqueous ammonia based on complexation with a crown ether is proposed.

Selective hydrodechlorination of fluorinated arylamines

Chlorine-containing polyfluorinated anilines and meta-phenylenediamines undergo selective hydrodechlorination easily upon reduction by zinc in aqueous ammonia. A new approach is thus provided to synthetically valuable, partially fluorinated arylamines based on utilizing polyfluorochloroarenes, which are available as intermediates of perfluoroarene production from perchloroarenes. When chlorine atoms are present in positions both ortho and para to the amino group, para chlorine is initially eliminated. Based on this reaction, a one-pot synthesis of partially fluorinated 4-aminopyridines from 3,5-dichlorotrifluoro- and 3-chlorotetrafluoropyridine has been realized.

Catalytic and noncatalytic ammonolysis of chloropentafluorobenzene

Ammonolysis of chloropentafluorobenzene both in the presence and in the absence of copper(I) salt results mainly in replacement of the para-and ortho-fluorine atoms with respect to chlorine rather than replacement of the chlorine atom. Ammonolysis of 4-chloro-2,3,5,6-tetrafluoroaniline and 2-chloro-3,4,5,6-tetrafluoroaniline in the absence of copper(I) salt yields exclusively the corresponding fluorine substitution products, whereas in the presence of copper(I) salt the chlorine atom is replaced. Successive ammonolysis of chloropentafluorobenzene in the presence of copper catalyst along these two paths was put into the basis of a new method for preparation of 2,3,5,6-tetrafluoro-1,4-phenylenediamine. * This study was financially supported by the Russian Foundation for Basic Research (project no. 99-03-33111), by the Ministry of Science and Technology of the Russian Federation (project no 9.3.01), and by the Ministry of Education of the Russian Federation (project no. 015.05.01.13).