446-32-2

Basic information

• Product Name: 2-Amino-4-fluorobenzoic acid
• Synonyms: TIMTEC-BB SBB006590;BUTTPARK 15\04-96;2-AMINO-4-FLUOROBENZOIC ACID;4-FLUOROANTHRANILIC ACID;2-Amino-4-FluorobenzoicAcid99%;2-Amino-4-Fluorobenzoic Acid 99%;2-Amino-4-fluorobenzoic;2-Amino-4-fluorobenzoicacid97%
• CAS NO: 446-32-2
• Molecular Formula: C₇H₆FNO₂
• Molecular Weight: 155.13
• EINECS: 207-163-9
• Product Categories: Fluorin-contained Benzoic acid series;Amines and Anilines;Amino Acids and Derivatives;Carboxylic Acids;Phenyls & Phenyl-Het;Benzoic acid;Chemical Amines;Amines;Aromatics;Carboxylic Acids;Phenyls & Phenyl-Het;Benzoic acid series;Fluorine series
• Mol File: 446-32-2.mol

Chemical Properties

• Melting Point: 192-196 °C(lit.)
• Boiling Point: 223.67°C (rough estimate)
• Flash Point: 146.2 °C
• Appearance: white to light yellow crystal powder
• Density: 1.3021 (estimate)
• Vapor Pressure: 0.331mmHg at 25°C
• Refractive Index: 1.509
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 4.88±0.10(Predicted)
• BRN: 2803665
• CAS DataBase Reference: 2-Amino-4-fluorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-fluorobenzoic acid(446-32-2)
• EPA Substance Registry System: 2-Amino-4-fluorobenzoic acid(446-32-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 446-32-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Amino-4-fluorobenzoic acid is used as a key intermediate in the synthesis of various organic compounds. Its unique structure and functional groups allow it to participate in a range of chemical reactions, making it a versatile building block for the creation of new molecules with potential applications in pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Amino-4-fluorobenzoic acid is utilized as a starting material for the development of new drugs. Its specific properties enable it to be incorporated into the molecular structures of potential therapeutic agents, targeting a variety of medical conditions.
Used in Agrochemical Industry:
2-Amino-4-fluorobenzoic acid also finds application in the agrochemical industry, where it is used as a precursor for the synthesis of various pesticides and other crop protection agents. Its unique chemical properties allow for the development of novel compounds with improved efficacy and selectivity.
Used in Research and Development:
In the field of research and development, 2-Amino-4-fluorobenzoic acid serves as an important compound for studying various chemical reactions and mechanisms. Its unique structure and properties make it an ideal candidate for exploring new reaction pathways and understanding the underlying chemistry involved.

InChI:InChI=1/C6H3F2NO2/c7-4-1-2-6(9(10)11)5(8)3-4/h1-3H

Upstream product

• 324-03-8 6-fluoroisatin 
• 394-27-4 2-acetamido-4-fluorobenzoic acid 
• 364-78-3 2-nitro-4-fluoroaniline 
• 80517-21-1 4-fluoro-2-nitrobenzonitrile 
• 367-29-3 3-fluoro-6-methylaniline 
• 366-49-4 5’-fluoro-2’-methylacetanilide 
• 119-32-4 4-Methyl-3-nitroanilin 
• 2475-81-2 methyl 4-fluoroanthranilate 
• 60-00-4 ethylenediaminetetraacetic acid 
• 1006-41-3 2-bromo-4-fluorobenzoic acid 
• 1863-63-4 ammonium benzoate 
• 459-56-3 4-fluorobenzylic alcohol 
• 446-10-6 2-nitro-4-fluorotoluene 
• 106754-80-7 4-fluoro-2-nitrobenzamide 

Downstream Products

• 2713-68-0 2-(carboxymethyl-amino)-4-fluoro-benzoic acid 
• 56096-89-0 4-fluoro-2-iodobenzoic acid 
• 197783-88-3 (2-amino-4-fluorophenyl)methanol 
• 81223-41-8 2,2’-disulfanediylbis(4-fluorobenzoic acid) 
• 16499-57-3 7-fluoro-3H-quinazolin-4-one 
• 321-50-6 7-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione 
• 190845-07-9 methyl 2-[N-(5-fluoro-2-carboxyphenyl)amino]benzoate 
• 81223-43-0 4-fluoro-2-sulfanyl-benzoic acid 
• 1026929-28-1 2-Amino-N-[(1R,2R)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-4-fluoro-benzamide 
• 886574-91-0 N-methoxy-N-methyl-2-amino-4-fluoro-benzamide 
• 16499-57-3 7-fluoro-3,4-dihydroquinazolin-4-one 
• 117324-05-7 2-amino-4-fluoro-benzoic acid ethyl ester 
• 642491-84-7 6-fluoro-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one 
• 97954-38-6 methyl 4-fluoro-2-(N-methylamino)benzoate 

Relevant articles and documents

Preparation method of 2-amino-4-fluorobenzoic acid

The invention relates to a preparation method of 2-amino-4-fluorobenzoic acid, which comprises the following steps: by taking cheap and easily available 4-fluorobenzyl alcohol as a raw material, firstly carrying out nitration reaction to obtain a nitro substitute, then carrying out oxidation reaction on the nitro substitute to obtain benzoic acid oxide, and finally carrying out reduction reaction on the benzoic acid oxide to finally obtain 2-amino-4-fluorobenzoic acid which is high in purity and high in yield. The preparation method disclosed by the invention has the characteristics of cheap and easily available raw materials, short reaction route, conventional reaction, mild reaction conditions, high yield and easiness in industrial production.

Discovery of Novel Tacrine-Pyrimidone Hybrids as Potent Dual AChE/GSK-3 Inhibitors for the Treatment of Alzheimer's Disease

Based on a multitarget strategy, a series of novel tacrine-pyrimidone hybrids were identified for the potential treatment of Alzheimer's disease (AD). Biological evaluation results demonstrated that these hybrids exhibited significant inhibitory activities toward acetylcholinesterase (AChE) and glycogen synthase kinase 3 (GSK-3). The optimal compound 27g possessed excellent dual AChE/GSK-3 inhibition both in terms of potency and equilibrium (AChE: IC50 = 51.1 nM; GSK-3β: IC50 = 89.3 nM) and displayed significant amelioration on cognitive deficits in scopolamine-induced amnesia mice and efficient reduction against phosphorylation of tau protein on Ser-199 and Ser-396 sites in glyceraldehyde (GA)-stimulated differentiated SH-SY5Y cells. Furthermore, compound 27g exhibited eligible pharmacokinetic properties, good kinase selectivity, and moderate neuroprotection against GA-induced reduction in cell viability and neurite damage in SH-SY5Y-derived neurons. The multifunctional profiles of compound 27g suggest that it deserves further investigation as a promising lead for the prospective treatment of AD.

Selenium-catalyzed intramolecular atom- And redox-economical transformation ofo-nitrotoluenes into anthranilic acids

Anthranilic acids (AAs) are significant basic chemicals used in pharmaceuticals, agrochemicals, dyes, fragrances,etc. Superfluous steps are always involved in obtaining AAs. Herein, we demonstrate a straightforward strategy to transform abundanto-nitrotoluenes into biologically and pharmaceutically significant AAs without any extra reductants, oxidants and protecting groups. Various sensitive groups, such as halogens, sulfide, aldehyde, pyridines, quinolines,etc., can be tolerated in this transformation. A hundred-gram-scale operation is realized efficiently with almost quantitative selenium recycling. Further mechanistic studies and DFT calculations disclosed the proposed atom-exchange processes and the key roles of the selenium species.

Anthranilic acid and derivatives thereof as well as synthesis method and application thereof

In the reaction solvent, o-methyl (hetero) aryl nitro compound is taken as a reaction raw material and is used for water. The anthranilic acid and its derivatives are synthesized by the action of a catalyst, a base and an additive. The synthetic method has the advantages of cheap and easily available raw materials, simple reaction operation, high yield and excellent functional group tolerance, and provides a simple and efficient method for synthesizing o-aminobenzoic acid which is widely used in the aspects of dyes, medicines, pesticides, spices and the like. The invention further discloses the anthranilic acid and derivatives and application thereof, and has a wide application prospect.

ARYLQUINAZOLINES

The invention relates to novel compounds of the formula (I) which can be used for the inhibition of serine-threonine protein kinases and for the sensitisation of cancer cells to anticancer agents and/or ionising radiation.

19F magnetic resonance probes for live-cell detection of peroxynitrite using an oxidative decarbonylation reaction

We report a newly discovered oxidative decarbonylation reaction of isatins that is selectively mediated by peroxynitrite (ONOO-) to provide anthranilic acid derivatives. We have harnessed this rapid and selective transformation to develop two reaction-based probes, 5-fluoroisatin and 6-fluoroisatin, for the low-background readout of ONOO- using 19F magnetic resonance spectroscopy. 5-fluoroisatin was used to non-invasively detect ONOO- formation in living lung epithelial cells stimulated with interferon-γ (IFN-γ). This journal is

Discovery of a novel series of 4-quinolone JNK inhibitors

A novel series of highly selective JNK inhibitors based on the 4-quinolone scaffold was designed and synthesized. Structure based drug design was utilized to guide the compound design as well as improvements in the physicochemical properties of the series. Compound (13c) has an IC50 of 62/170 nM for JNK1/2, excellent kinase selectivity and impressive efficacy in a rodent asthma model.

Condensed pyrazole derivatives, process for producing the same and use thereof

Novel pharmaceutical compositions for inhibiting Th2-selective immune response and pharmaceutical compositions for inhibiting cyclooxygenase comprising condensed pyrazole derivatives represented by the general formula (I): or salts thereof.

PROCESS FOR THE MANUFACTURE OF 4-FLUORO-ANTHRANILIC ACID

The present invention concerns a process for preparing 4-fluoro-anthranilic acid by nitration, reduction and hydrolysis of an alkyl 3-chloro-4-fluorobenzoate.

Process for the preparation of haloanthranilic acids

The present invention relates to a process for the preparation of compounds of the general formula I STR1 in which X and Y, independently of each other, represent hydrogen, fluorine, chlorine or bromine, but cannot simultaneously represent hydrogen, characterised in that compounds of the general formula II STR2 in which X and Y are defined as above, are reacted with aqueous ammonia under copper catalysis, and to intermediates for the preparation of compounds of the general formula I.