5580-80-3

Basic information

• Product Name: 2,3,4,5-Tetrafluoroaniline
• Synonyms: 2,3,4,5-Tetrafluoroa;2,3,4,5-tetrafluoroethane aniline;Benzenamine, 2,3,4,5-tetrafluoro-;2,3,4,5-TETRAFLUOROANILINE;2,3,4,5-TETRAFLUORO-PHENYLAMINE;Aniline, 2,3,4,5-tetrafluoro-;4-flurophenylacetic acid;2,3,4,5-Tetrafluoroaniline 98%
• CAS NO: 5580-80-3
• Molecular Formula: C₆H₃F₄N
• Molecular Weight: 165.09
• EINECS: 276-218-7
• Product Categories: Aniline;Amines;C2 to C6;Nitrogen Compounds
• Mol File: 5580-80-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 27-29 °C(lit.)
• Boiling Point: 78 °C13 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: White to brown/Powder
• Density: 1.4700 (estimate)
• Vapor Pressure: 0.527mmHg at 25°C
• Refractive Index: 1.4670 to 1.4710
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.23±0.10(Predicted)
• CAS DataBase Reference: 2,3,4,5-Tetrafluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-Tetrafluoroaniline(5580-80-3)
• EPA Substance Registry System: 2,3,4,5-Tetrafluoroaniline(5580-80-3)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39
• RIDADR: 2810
• WGK Germany: 3
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• PackingGroup: Ⅲ
• Hazardous Substances Data: 5580-80-3(Hazardous Substances Data)

Usage

General Description

2,3,4,5-Tetrafluoroaniline is a chemical compound with the formula C6H4F4N. It is a substituted aniline, meaning it is an aromatic amine with four fluorine atoms attached to the benzene ring along with an amino group. 2,3,4,5-Tetrafluoroaniline is used in the production of various pharmaceuticals, agrochemicals, and dyes. It has also been studied for its potential use in organic electronics and as a building block in the synthesis of novel materials. 2,3,4,5-Tetrafluoroaniline is considered to be a hazardous substance, and proper safety measures should be implemented when handling and storing this chemical.

InChI:InChI=1/C6H3F4N/c7-2-1-3(11)5(9)6(10)4(2)8/h1H,11H2

Upstream product

• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 653-22-5 1-Acetylamino-2,3,4,5,6-pentafluorobenzen 
• 16582-88-0 N-(2,3,4,5-tetrafluorophenyl)acetamide 
• 1765-42-0 2-amino-3,4,5,6-tetrafluorobenzoic acid 
• 5580-81-4 2-Brom-3,4,5,6-tetrafluor-acet-anilid 
• 16582-99-3 2-NH₂-C₆F₄CN 
• 5580-82-5 2-bromo-3,4,5,6-tetrafluoroaniline 
• 551-62-2 1,2,3,4-tetrafluorobenzene 
• 16583-00-9 2-NH₂C₆F₄C(O)NH₂ 
• 5580-79-0 2,3,4,5-tetrafluoro-1-nitrobenzene 

Downstream Products

• 1765-42-0 2-amino-3,4,5,6-tetrafluorobenzoic acid 
• 1228813-89-5 2-iodo-3,4,5,6-tetrafluoroaniline 
• 16582-88-0 N-(2,3,4,5-tetrafluorophenyl)acetamide 

Relevant articles and documents

Interaction of polyfluorinated 2-chloroquinolines with ammonia

We have studied the interaction of polyfluorinated (in the benzene moiety) 2-chloroquinolines with liquid and aqueous ammonia as an approach to the synthesis of halogen-containing aminoquinolines. 5,7-Difluoro-, 5,6,8-trifluoro-, and 5,7,8-trifluoro-2-chloroquinolines mostly form products of substitution of the Cl atom, whereas 5,7-difluoro-2,6-dichloroquinoline, 5,6,7,8-tetrafluoro-, and 6,7-difluoro-2-chloroquinolines yield products of substitution of an F atom at various positions. The replacement of liquid ammonia with aqueous causes an increase in the proportion of the products of aminodechlorination relative to the products of aminodefluorination. For 2-chloro-6,8-difluoroquinoline this replacement leads to 2-amino-6,8-difluoroquinoline as the main product instead of the 8-amino-derivative. Activation energy values estimated by DFT calculations for the reactions in question agree with the reaction regioselectivity observed experimentally.

Synthesis of polyfluorinated 4-phenyl-3,4-dihydroquinolin-2-ones and quinolin-2-ones via superacidic activation of N-(polyfluorophenyl)cinnamamides

The cyclization reactions of a series of polyfluorocinnamanilides in triflic acid (CF3SO3H) yield 4-phenyl-3,4-dihydroquinolin-2-ones, which include a polyfluorinated benzene moiety as a part of the quinoline scaffold. These compounds undergo dehydrophenylation in the presence of AlCl3 to give the corresponding polyfluoroquinolin-2-ones which are converted into polyfluorinated 2-chloroquinolines on treatment with POCl3. A mechanism for the cyclization reaction presuming the intermediacy of a superelectrophilic O,C-diprotonated form of the starting material is suggested.