Names | |
---|---|
Preferred IUPAC name
Pentafluorobenzoic acid | |
Other names
perfluorobenzoic acid
| |
Identifiers | |
3D model (
JSmol)
|
|
2054395 | |
ChemSpider | |
ECHA InfoCard | 100.009.115 |
2054395 | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C7HF5O2 | |
Molar mass | 212.075 g·mol−1 |
Appearance | White crystalline powder |
Density | 1.942 g/cm3 |
Melting point | 100–102 °C (212–216 °F; 373–375 K) |
Boiling point | 220 °C (428 °F; 493 K) |
Very soluble | |
log P | 2.06 |
Acidity (pKa) | 1.60 |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | 87 °C (189 °F; 360 K) |
Related compounds | |
Related
carboxylic acids
|
benzoic acids, Nitrobenzoic acids |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Pentafluorobenzoic acid (PFBA) is an organofluorine compound with the formula C6F5CO2H. It is a white crystalline powder that has a high solubility in water. Its pKa of 1.48 indicates that it is a strong acid. [1]
Pentafluorobenzoic acid is prepared by treating pentafluorophenyllithium (or pentafluorophenyl Grignard reagent) with carbon dioxide. These reagents are usually prepared in situ from pentafluorobenzene and bromopentafluorobenzene. [1] [2]
It arises via the reaction of perfluorotoluene with trifluoroacetic acid and antimony pentafluoride. [3]
Substitution of fluoride occurs typically at the para position. This reaction has been used to anchor the −C6F4CO2H group to surfaces. Magnesium methoxide results in ortho methoxylation. Cleavage of this ether gives tetrafluorosalicylic acid. Via similar ortho-directed reactivity, nickel complexes catalyse the defluoridation of 2 and 5 positions. Without nickel, defluoridation occurs with para-selectivity. [1]
Names | |
---|---|
Preferred IUPAC name
Pentafluorobenzoic acid | |
Other names
perfluorobenzoic acid
| |
Identifiers | |
3D model (
JSmol)
|
|
2054395 | |
ChemSpider | |
ECHA InfoCard | 100.009.115 |
2054395 | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C7HF5O2 | |
Molar mass | 212.075 g·mol−1 |
Appearance | White crystalline powder |
Density | 1.942 g/cm3 |
Melting point | 100–102 °C (212–216 °F; 373–375 K) |
Boiling point | 220 °C (428 °F; 493 K) |
Very soluble | |
log P | 2.06 |
Acidity (pKa) | 1.60 |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | 87 °C (189 °F; 360 K) |
Related compounds | |
Related
carboxylic acids
|
benzoic acids, Nitrobenzoic acids |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Pentafluorobenzoic acid (PFBA) is an organofluorine compound with the formula C6F5CO2H. It is a white crystalline powder that has a high solubility in water. Its pKa of 1.48 indicates that it is a strong acid. [1]
Pentafluorobenzoic acid is prepared by treating pentafluorophenyllithium (or pentafluorophenyl Grignard reagent) with carbon dioxide. These reagents are usually prepared in situ from pentafluorobenzene and bromopentafluorobenzene. [1] [2]
It arises via the reaction of perfluorotoluene with trifluoroacetic acid and antimony pentafluoride. [3]
Substitution of fluoride occurs typically at the para position. This reaction has been used to anchor the −C6F4CO2H group to surfaces. Magnesium methoxide results in ortho methoxylation. Cleavage of this ether gives tetrafluorosalicylic acid. Via similar ortho-directed reactivity, nickel complexes catalyse the defluoridation of 2 and 5 positions. Without nickel, defluoridation occurs with para-selectivity. [1]