Compounds > pentafluorobenzoic acid
Page last updated: 2024-11-05

pentafluorobenzoic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Pentafluorobenzoic acid (PFBA) is a highly fluorinated aromatic carboxylic acid. It is a colorless solid with a melting point of 103-104 °C and a boiling point of 245 °C. PFBA is synthesized by the reaction of pentafluorobenzene with carbon dioxide in the presence of a strong base, such as potassium hydroxide. It is a versatile building block for the preparation of other fluorinated compounds, including pharmaceuticals, agrochemicals, and materials science. PFBA has been studied for its potential use as a flame retardant, a surfactant, and a component of lithium-ion batteries. It is also used as a reagent in organic synthesis and as a standard in analytical chemistry. PFBA is known to be a potent inhibitor of the enzyme carbonic anhydrase, which is involved in the regulation of carbon dioxide levels in the body. Studies have shown that PFBA can have adverse effects on the environment and human health, including toxicity to aquatic organisms and potential endocrine disruption.'

Cross-References

ID SourceID
PubMed CID11770
CHEMBL ID3092378
CHEBI ID46796
SCHEMBL ID203915
MeSH IDM0239971

Synonyms (39)

Synonym
nsc88337
perfluorobenzoic acid
nsc-88337
602-94-8
2,3,4,5,6-pentafluoro-benzoic acid
pentafluorobenzoic acid
benzoic acid, pentafluoro-
nsc 88337
einecs 210-026-6
brn 2054395
2,3,4,5,6-pentafluorobenzoic acid, 99%
CHEBI:46796 ,
2,3,4,5,6-pentafluorobenzoic acid
NCIOPEN2_005348
AC-4654
yzerdtreousuhf-uhfffaoysa-
inchi=1/c7hf5o2/c8-2-1(7(13)14)3(9)5(11)6(12)4(2)10/h(h,13,14)
P0806
AKOS000119713
A8421
2,3,4,5,6-pentafluorobenzoicacid
c7hf5o2
benzoic acid, 2,3,4,5,6-pentafluoro-
b4jcp8r5gj ,
unii-b4jcp8r5gj
4-09-00-00956 (beilstein handbook reference)
FT-0609327
CHEMBL3092378
SCHEMBL203915
DTXSID4060527
W-105266
mfcd00002406
D72572
CS-0030580
AS-11945
EN300-20106
AMY3640
PB47373
Z104476874

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Urinary excretion in bile-cannulated animals was similar to that found in studies using non-cannulated animals dosed at 100mg kg(-1)."( Application of (1)H- and (19)F-NMR spectroscopy in the investigation of the urinary and biliary excretion of 3,5-, 2,4-ditrifluoromethylbenzoic and pentafluorobenzoic acids in rat.
Blackledge, CA; Evans, JA; Nicholson, JK; Rodgers, C; Wilson, ID, 2002)		0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
perfluorinated compoundAn organofluorine compound containing only C-F bonds (no C-H bonds) and C-C bonds but also other heteroatoms (particularly other halogens, oxygen, and sulfur). Their properties represent a blend of fluorocarbons (containing only C-F and C-C bonds) and the parent functionalised organic species.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1059430Inhibition of recombinant human IDO1 expressed in Escherichia coli EC538 using L-tryptophan as substrate at 1 mM after 1 hr relative to control2013Bioorganic & medicinal chemistry, Dec-15, Volume: 21, Issue:24
Discovery and characterisation of hydrazines as inhibitors of the immune suppressive enzyme, indoleamine 2,3-dioxygenase 1 (IDO1).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (12.50)18.2507
2000's9 (56.25)29.6817
2010's5 (31.25)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.52

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index29.52 (24.57)
Research Supply Index3.00 (2.92)
Research Growth Index4.90 (4.65)
Search Engine Demand Index31.18 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.52)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
4-hydroxybenzaldehyde
[no description available]		2.0810hydroxybenzaldehydeEC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor;
mouse metabolite;
plant metabolite
benzoic acid
Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.		2.1110benzoic acidsalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite
bromide
Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)		2.9840halide anion;
monoatomic bromine
catechol
[no description available]		2.0810catecholsallelochemical;
genotoxin;
plant metabolite
salicylic acid
Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).		2.0810monohydroxybenzoic acidalgal metabolite;
antifungal agent;
antiinfective agent;
EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor;
keratolytic drug;
plant hormone;
plant metabolite
2-aminoadipic acid
2-Aminoadipic Acid: A metabolite in the principal biochemical pathway of lysine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-METHYL-D-ASPARTATE; (NMDA).. 2-aminoadipic acid : An alpha-amino acid that is adipic acid bearing a single amino substituent at position 2. An intermediate in the formation of lysine.		2.0110amino dicarboxylic acid;
dicarboxylic fatty acid;
non-proteinogenic alpha-amino acid		Caenorhabditis elegans metabolite;
mammalian metabolite
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		2.0110elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
nitrates
Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.		2.1710monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species
phenanthrene
phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'		2.0210ortho-fused polycyclic arene;
ortho-fused tricyclic hydrocarbon;
phenanthrenes		environmental contaminant;
mouse metabolite
toluene
methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.		2.1710methylbenzene;
toluenes;
volatile organic compound		cholinergic antagonist;
fuel additive;
neurotoxin;
non-polar solvent
urea
pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.		2.1110isourea;
monocarboxylic acid amide;
one-carbon compound		Daphnia magna metabolite;
Escherichia coli metabolite;
fertilizer;
flour treatment agent;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
alachlor
alachlor : An aromatic amide that is N-(2,6-diethylphenyl)acetamide substituted by a methoxymethyl group at at the nitrogen atom while one of the hydrogens of the methyl group has been replaced by a chlorine atom.		2.0210aromatic amide;
monocarboxylic acid amide;
organochlorine compound		environmental contaminant;
herbicide;
xenobiotic
amphetamine
Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.		1.9810primary amine
triclosan
[no description available]		2.0510aromatic ether;
dichlorobenzene;
monochlorobenzenes;
phenols		antibacterial agent;
antimalarial;
drug allergen;
EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
fungicide;
persistent organic pollutant;
xenobiotic
benzoxazolone
benzoxazolone: RN given refers to parent cpd; structure. 2-benzoxazolinone : A member of the class of benzoxazoles that is 2,3-dihydro-1,3-benzoxazole carrying an oxo group at position 2.		2.0810benzoxazoleallelochemical;
phytoalexin
4-nitrobenzoic acid
4-nitrobenzoic acid: RN given refers to parent cpd. 4-nitrobenzoic acid : A nitrobenzoic acid having the nitro group at the 4-position.		2.0810nitrobenzoic acid
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		2.1110amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
bisphenol a
4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.		2.0510bisphenolendocrine disruptor;
environmental contaminant;
xenobiotic;
xenoestrogen
3-methylsalicylic acid
3-methylsalicylic acid : A monohydroxybenzoic acid consisting of salicylic acid carrying a methyl group at the 3-position.		2.0810monohydroxybenzoic acidbacterial xenobiotic metabolite
1,5-dihydroxynaphthalene
[no description available]		2.0810
5-methylsalicylic acid
[no description available]		2.0810
4,4'-dihydroxybiphenyl
biphenyl-4,4'-diol : A member of the class of hydroxybiphenyls that is biphenyl with hydroxy groups at positions 4 and 4'.		2.0810hydroxybiphenyls
benzothiazole
benzothiazole: structure. benzothiazole : An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.		2.0810benzothiazolesenvironmental contaminant;
plant metabolite;
xenobiotic
phenylhydrazine
[no description available]		2.0810phenylhydrazinesxenobiotic
dibenzothiazyl disulfide
dibenzothiazyl disulfide: vulcanizing accelerant. dibenzothiazol-2-yl disulfide : An organic disulfide resulting from the formal oxidative coupling of the thiol groups of two molecules of 1,3-benzothiazole-2-thiol. It is used as an accelerator in the rubber industry.		2.0810benzothiazoles;
organic disulfide		allergen
2-aminobenzothiazole
[no description available]		2.0810benzothiazoles
2,6-difluorobenzoic acid
2,6-difluorobenzoic acid: structure given in first source		2.1710
2-trifluoromethylbenzoic acid
[no description available]		2.1710(trifluoromethyl)benzenes;
benzoic acids
4-methylcatechol
[no description available]		2.0810methylcatecholantioxidant;
carcinogenic agent;
hapten;
human metabolite;
plant metabolite
fluorobenzenes
Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.		1.9810monofluorobenzenesNMR chemical shift reference compound
ninhydrin
Ninhydrin: 2,2-Dihydroxy-1H-indene-1,3-(2H)-dione. Reagent toxic to skin and mucus membranes. It is used in chemical assay for peptide bonds, i.e., protein determinations and has radiosensitizing properties.. ninhydrin : A member of the class of indanones that is indane-1,3-dione bearing two additional hydroxy substituents at position 2.		2.0810aromatic ketone;
beta-diketone;
indanones;
ketone hydrate		colour indicator;
human metabolite
hydroxyhydroquinone
benzene-1,2,4-triol : A benzenetriol carrying hydroxy groups at positions 1, 2 and 4.		2.0810benzenetriolmouse metabolite
6-hydroxyquinoline
quinolin-6-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 6.		2.0810monohydroxyquinoline
2,7-dihydroxynaphthalene
[no description available]		2.0810
1,3-indandione
1,3-indandione : A member of the class of indanones that is indane in which the hydrogens at positions 2 and 4 have been replaced by oxo groups.		2.0810aromatic ketone;
beta-diketone;
indanones
5-methylbenzimidazole
5-methylbenzimidazole: structure in first source. 5-methyl-1H-benzimidazole : A member of the class of imidazoles that is 1H-benzimidazole in which the hydrogen at position 5 is substituted by a methyl group.		2.0810imidazoles
2-hydrazinobenzothiazole
[no description available]		2.0810
3-acetylindole
3-acetylindole: structure in first source		2.0810
2-hydroxybenzothiazole
2-hydroxybenzothiazole : Benzothiazole substituted with a hydroxy group at the 2-position.		2.0810benzothiazole
methylphosphonic acid
methylphosphonic acid : A one-carbon compound that is phosphonic acid in which the hydrogen attached to the phosphorus is substituted by a methyl group.		2.1710one-carbon compound;
phosphonic acids
phenylhydroquinone
phenylhydroquinone: major metabolite of o-phenylphenol; cleaves DNA; structure given in first source		2.0810
2-amino-4-methylbenzothiazole
2-amino-4-methylbenzothiazole: structure in first source		2.0810
2,2'-biphenol
biphenyl-2,2'-diol : A member of the class of hydroxybiphenyls carrying hydroxy groups at positions 2 and 2'.		2.0810hydroxybiphenyls
platinum
Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.		7.0510elemental platinum;
nickel group element atom;
platinum group metal atom
titanium
Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.		2.0510titanium group element atom
deuterium
Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.		1.9810dihydrogen
fluorine
Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.		2.0110diatomic fluorine;
gas molecular entity		NMR chemical shift reference compound
titanium dioxide
titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.		2.0510titanium oxidesfood colouring
fluorides
[no description available]		2.0510halide anion;
monoatomic fluorine
salicylhydroxamic acid
[no description available]		2.0810hydroxamic acid;
phenols		antibacterial drug;
EC 1.11.2.2 (myeloperoxidase) inhibitor;
EC 3.5.1.5 (urease) inhibitor;
trypanocidal drug
5-fluorosalicylic acid
5-fluorosalicylic acid: structure given in first source; product from action of alkaline phosphatase on 5-fluorosalicyl phosphate; forms highly fluorescent terbium ternary complex		2.0810
1,8-diaminonaphthalene
1,8-diaminonaphthalene: structure in first source		2.0810
4(5)-phenylimidazole
4(5)-phenylimidazole: tautomeric cpd; cytochrome P450 14alpha-sterol demethylase, CYP51 antagonist		2.0810
trimethylphosphine oxide
trimethylphosphine oxide: structure in first source		2.1110
biphenyl-2-carboxylic acid
biphenyl-2-carboxylic acid: structure in first source		2.0810
pentafluorobenzoyl chloride
pentafluorobenzoyl chloride: RN given refers to parent cpd. pentafluorobenzoyl chloride : The acid chloride of pentafluorobenzoic acid. It is a sensitive derivatising reagent for the analysis of amines, amides and phenols by electron capture gas chromatography.		1.9810acyl chloride;
perfluorinated compound		chromatographic reagent
4-Methoxybenzamide
[no description available]		2.0810benzamides
2-(carboxymethylthio)benzothiazole
2-(carboxymethylthio)benzothiazole: oxidation product of 2-(hydroxyethylthio)benzothiazole; structure given in first source		2.0810
2,6-dihydroxynaphthalene
[no description available]		2.0810naphthols
organophosphonates
hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.		2.4720divalent inorganic anion;
phosphite ion
potassium bromide
potassium bromide : A metal bromide salt with a K(+) counterion.		2.1710potassium salt
ethyl methylphosphonic acid
ethyl methylphosphonic acid: urinary sarin metabolite		2.1710
captax
captax: RN given refers to parent cpd. 1,3-benzothiazole-2-thiol : 1,3-Benzothiazole substituted at the 2-position with a sulfanyl group.		2.0810aryl thiol;
benzothiazoles		carcinogenic agent;
metabolite
4-nitrocatechol
4-nitrocatechol : A member of the class of catechols that is benzene-1,2-diol substituted by a nitro group at position 4.It is the by-product of the hydroxylation of p-nitrophenol.		2.0810C-nitro compound;
catechols		human xenobiotic metabolite;
lipoxygenase inhibitor
esculetin
esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.		2.0810hydroxycoumarinantioxidant;
plant metabolite;
ultraviolet filter
7-hydroxycoumarin-4-acetic acid
7-hydroxycoumarin-4-acetic acid: pH-indicator dye; structure in first source		2.0810
phenanthrenes
Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.		2.0210
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.9440