651-83-2

Basic information

• Product Name: 2,3,5,6-TETRAFLUORO-4-AMINOBENZOTRIFLUORIDE
• Synonyms: 4-AMINO-2,3,5,6-TETRAFLUOROBENZOTRIFLUORIDE;4-AMINO-HEPTAFLUOROTOLUENE;AKOS B014369;2,3,5,6-TETRAFLUORO-4-AMINOBENZOTRIFLUORIDE;2,3,5,6-TETRAFLUORO-4-(TRIFLUOROMETHYL)ANILINE;2,3,5,6,ALPHA,ALPHA,ALPHA-HEPTAFLUORO-P-TOLUIDINE;2,3,5,6,α,α,α-heptafluoro-p-toluidine;4-AMINO-HEPTAFLUOROTOLUENE 95% (GC)
• CAS NO: 651-83-2
• Molecular Formula: C₇H₂F₇N
• Molecular Weight: 233.09
• Mol File: 651-83-2.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 186 °C(lit.)
• Flash Point: 190 °F
• Appearance: Clear colourless to light brown liquid
• Density: 1.687 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.38mmHg at 25°C
• Refractive Index: n20/D 1.431(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -2.05±0.10(Predicted)
• BRN: 2657893
• CAS DataBase Reference: 2,3,5,6-TETRAFLUORO-4-AMINOBENZOTRIFLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-TETRAFLUORO-4-AMINOBENZOTRIFLUORIDE(651-83-2)
• EPA Substance Registry System: 2,3,5,6-TETRAFLUORO-4-AMINOBENZOTRIFLUORIDE(651-83-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 651-83-2(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to light brown liquid

InChI:InChI=1/C7H2F7N/c8-2-1(7(12,13)14)3(9)5(11)6(15)4(2)10/h15H2

Upstream product

• 80850-06-2 1,2,4,5-tetrafluoro-3-nitro-6-(trifluoromethyl)benzene 
• 627-51-0 divinyl sulfide 
• 434-64-0 perfluorotoluene 
• 1868-85-5 (2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)hydrazine 
• 530102-88-6 1-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-4-trimethylsilyl-2,4-diaza-1,3-dithia-2,3-butadiene 
• 1693-30-7 4-CF₃-C₆F₄NHNCHC₆H₅ 
• 105637-41-0 4-trifluoromethyl-2,3,5,6-tetrafluorophenylhydroxylamine 
• 100758-21-2 benzylidene 4-trifluoromethyl-2,3,5,6-tetrafluoroaniline 

Downstream Products

• 63995-40-4 C₇Cl₂F₇N 
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• 98583-25-6 4,4'-bis-(trifluoromethyl)-octafluoroazoxybenzene 
• 93832-48-5 2,3,5,6-tetrafluoro-2',4',6'-trimethyl-4-(trifluoromethyl)azobenzene 
• 71153-93-0 2,3,4,5,6-Pentafluoro-N-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-benzimidoyl chloride 
• 1346459-81-1 4-bromo-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)biphenyl-2-carboxamide 
• 1327280-93-2 3-methyl-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)biphenyl-2-carboxamide 
• 1346459-86-6 7-methyl-5-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydrophenanthridin-6(5H)-one 
• 1346459-77-5 2-(6-methoxynaphthalen-2-yl)-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]propanamide 
• 1346459-84-4 2-(6-methoxy-3-phenylnaphthalen-2-yl)-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)propanamide 
• 1346459-80-0 4-chloro-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)biphenyl-2-carboxamide 
• 1346459-78-6 N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)biphenyl-2-carboxamide 
• 1346459-82-2 5-methoxy-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)biphenyl-2-carboxamide 
• 1346459-76-4 2-(4-isobutylphenyl)-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]propanamide 

Relevant articles and documents

Palladium-Catalyzed C-H Silylation of Aliphatic Ketones Using an Aminooxyamide Auxiliary

A palladium-catalyzed β-C(sp3)-H silylation of aliphatic ketones with disilanes to afford β-silyl ketones is reported. The aminooxyamide auxiliary is critical for the C-H activation and silylation. The reaction tolerates a number of functional groups and

Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control

The photocatalytic C-F functionalization of highly fluorinated arenes is a powerful method for accessing functionalized multifluorinated arenes. The decisive step in the determining regioselectivity in fluorine functionalization is fluoride fragmentation from the radical anion of the multifluorinated arene. To date, the availability of regioisomers has been dictated by the innate electronics of the fluorinated arene, limiting the synthetic utility of the chemistry. This study investigates the remarkable ability of a strategically located hydrogen bond to transcend the normal regioselectivity of the C-F functionalization event. A significant rate acceleration is additionally observed for hydrodefluorination of fluorines that can undergo intramolecular hydrogen bonds that form 5-8-membered cycles with moderately acidic N-H's. The hydrogen bond is expected to facilitate the fragmentation not only by bending the C-F bond of the radical anion out of planarity but also by increasing the exothermicity of the fluoride extrusion step through protonation of the naked fluoride. Finally, the synthetic utility of the method is demonstrated in an expedited synthesis of the trifluorinated α-phenyl acetic acid derivative required for the commercial synthesis of Januvia, an antidiabetic drug. This represents the first synthesis of a commercially important multifluorinated arene via a defluorination strategy and is significantly shorter than the current strategy.

PALLADIUM(II)-CATALYZED SELECTIVE FLUORINATION OF BENZOIC ACIDS AND DERIVATIVES

A new method of ortho-fluorination for selectively fluorinating a benzoic acid or derivative compound where an aryl C—H bond is directly replaced by an aryl C—F bond is provided. The method comprises reacting a compound having the formula: wherein X is at