2,3,4,5,6-Pentafluoroaniline

Base Information

• Chemical Name: 2,3,4,5,6-Pentafluoroaniline
• CAS No.: 771-60-8
• Molecular Formula: C6H2F5N
• Molecular Weight: 183.081
• Hs Code.: 29214210
• European Community (EC) Number: 212-234-2
• NSC Number: 88320
• UNII: MS06IL3Y2Q
• DSSTox Substance ID: DTXSID8022119
• Nikkaji Number: J1.734E
• Wikidata: Q27284202
• Mol file: 771-60-8.mol

Synonyms:Aniline,2,3,4,5,6-pentafluoro- (6CI,7CI,8CI);1-Amino-2,3,4,5,6-pentafluorobenzene;Aminopentafluorobenzene;NSC 88320;Pentafluoroaniline;Pentafluorophenylamine;

Chemical Property of 2,3,4,5,6-Pentafluoroaniline

Chemical Property:

• Appearance/Colour: white to salmon crystalline low melting solid
• Vapor Pressure: 3.69mmHg at 25°C
• Melting Point: 33-35 °C(lit.)
• Refractive Index: 1.429
• Boiling Point: 156.4 °C at 760 mmHg
• PKA: -0.16±0.10(Predicted)
• Flash Point: 73.9 °C
• PSA: 26.02000
• Density: 1.623 g/cm³
• LogP: 2.54550
• Storage Temp.: Store below +30°C.
• Solubility.: toluene: soluble
• Water Solubility.: Soluble in toluene, and organic solvents. Insoluble in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 183.01073988
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

Pentafluoroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1(=C(C(=C(C(=C1F)F)F)F)F)N
• Uses: 2,3,4,5,6-Pentafluoroaniline finds it uses in the preparation of pentafluorophenylammonium triflate, an efficient catalyst for esterification and thioesterification. It is also used in the synthesis of various titanium complexes having two anionic [N, O-] bidentate salicylaldiminato ligands.

Technology Process of 2,3,4,5,6-Pentafluoroaniline

There total 45 articles about 2,3,4,5,6-Pentafluoroaniline 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: 92.0%

2,3,4,5,6-pentafluorobenzamide (652-31-3) → 2,3,4,5,6-pentafluoroaniline (771-60-8)

Guidance literature:

With bromine; sodium hydroxide; In water; acetonitrile; at 80 ℃; Reagent/catalyst; Solvent; Temperature;

Reference yield: 87.0%

1,2,3,4,5-pentafluoro-6-iodobenzene (827-15-6) → 2,3,4,5,6-pentafluoroaniline (771-60-8)

Guidance literature:

With ammonium hydroxide; copper(I) iodide; 1-ethylacetoacetate-3-methyl imidazolium hydroxide; In acetonitrile; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tet.2013.04.088

Reference yield: 87.0%

Hexafluorobenzene (392-56-3) → 2,3,4,5,6-pentafluoroaniline (771-60-8)

Guidance literature:

With ammonia; at 100 ℃; for 15h;

DOI:10.1007/s11172-007-0351-2

upstream raw materials:

Hexafluorobenzene

pentafluoronitrobenzen

Cyclopentane

perfluorophenyl azide

Downstream raw materials:

1,1,3,3,5,5,7,7-octamethyl-2,6-bis(pentafluorophenyl)-cyclo-1,3,5,7-tetrasila-2,6-diaza-4,8-dioxane

2,3,4,5,6-pentafluoro-N-(pentafluorophenyl)benzamide

2,2,3,3,4,4-Hexafluoro-4-pentafluorophenylazo-butyric acid methyl ester

2,2,3,3-Tetrafluoro-3-pentafluorophenylazo-propionic acid methyl ester

Refernces

Synthesis and elastase-inhibiting activity of 2-pyridinyl-isothiazol-3(2H)-one 1,1-dioxides

10.1016/j.bmc.2008.07.049

The research aims to synthesize and evaluate a series of new isothiazol-3(2H)-one 1,1-dioxides with halogenated (mostly fluorinated) pyridinyl and pentafluorophenyl substituents at the 2-position for their inhibitory activity against human leukocyte elastase (HLE). The compounds were synthesized using an isothiazolium cyclization–oxidation route from 2-thiocyanato-1-carboxaldehydes and aminopyridines or pentafluoroaniline. The study found that compound 21 exhibited an IC50 value of 3.1 μM toward HLE, indicating significant inhibitory activity. Other enzymes like cathepsin G, trypsin, cathepsin L, and angiotensin-converting enzyme, as well as the serine esterases acetylcholinesterase and cholesterol esterase, were not inhibited by compound 21. The research concludes that these compounds, especially those with tetrafluoropyridinyl substitution, show promise as selective HLE inhibitors, which could be useful in treating inflammatory diseases associated with HLE overactivity.