2365-85-7

Basic information

• Product Name: 3-Amino-4-fluorobenzoic acid
• Synonyms: 3-AMino-4-fluorobenzoic Acid, 97+%;Benzoicacid, 3-amino-4-fluoro-;3-AMINO-4-FLUOROBENZOIC ACID;3-Amino-4-Fluorobenzoic;3-azanyl-4-fluoro-benzoic acid;5-Carboxy-2-fluoroaniline
• CAS NO: 2365-85-7
• Molecular Formula: C₇H₆FNO₂
• Molecular Weight: 155.13
• EINECS: 219-122-2
• Product Categories: Fluorine series;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid series
• Mol File: 2365-85-7.mol

Chemical Properties

• Melting Point: 184 °C
• Boiling Point: 335.5 °C at 760 mmHg
• Flash Point: 156.7 °C
• Appearance: Off-white/Powder
• Density: 1.43 g/cm³
• Vapor Pressure: 574mmHg at 25°C
• Refractive Index: 1.336
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 4.30±0.10(Predicted)
• CAS DataBase Reference: 3-Amino-4-fluorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-4-fluorobenzoic acid(2365-85-7)
• EPA Substance Registry System: 3-Amino-4-fluorobenzoic acid(2365-85-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 2365-85-7(Hazardous Substances Data)

Usage

Chemical Properties

off-white powder

InChI:InChI=1/C4H9F/c1-2-3-4-5/h2-4H2,1H3

Upstream product

• 453-71-4 3-nitro-4-fluorobenzoic acid 
• 456-22-4 4-Fluorobenzoic acid 

Downstream Products

• 401-37-6 3‐acetamido‐4‐fluorobenzoic acid 
• 227609-86-1 (3-amino-4-fluorophenyl)methanol 
• 639859-08-8 4-fluoro-3-((2-(pyridin-2-ylamino)thiazol-5-ylmethyl)amino)benzoic acid 
• 918121-77-4 3-(tert-butoxycarbonylmethyl-amino)-4-fluoro-benzoic acid 
• 227609-88-3 4-fluoro-3-iodobenzaldehyde 
• 227609-87-2 (4-fluoro-3-iodophenyl)methanol 
• 227609-71-4 9-(4-Fluoro-3-iodophenyl)-2,3,5,6,7,9-hexahydrothieno[3,2-b]quinolin-8(4H)-one,1,1-dioxide 
• 632625-00-4 3-{2-[5-chloro-2-(benzyloxy)phenyl]-5-methyl-pyrrol-1-yl}-4-fluorobenzoic acid 
• 632623-78-0 3-{2-[5-fluoro-2-(4-fluorobenzyloxy)phenyl]-5-methyl-pyrrol-1-yl}-4-fluoro-benzoic acid 
• 632624-31-8 3-{2-[5-chloro-2-(2,6-difluorobenzyloxy)phenyl]-5-methyl-pyrrol-1-yl}-4-fluorobenzoic acid 
• 632624-42-1 3-{2-[5-chloro-2-(2,3-difluorobenzyloxy)phenyl]-5-methyl-pyrrol-1-yl}-4-fluorobenzoic acid 
• 115087-01-9 N-(2-fluoro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide 
• 1235560-82-3 (R)-(3-amino-4-fluorophenyl)(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)methanone 
• 639858-51-8 3-amino-N-cyclopropyl-4-fluorobenzamide 

Relevant articles and documents

Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold

Using a Tube-in-Tube device based on the amorphous Teflon AF-2400 fluoropolymer, a series of nitroarenes was hydrogenated to afford the corresponding aniline compounds. The system was then applied to the construction of a pyrrolobenzo[1,4]diazapene scaffold through a tandem hydrogenation-condensation-hydrogenation sequence.

Aromatic triazole foldamers induced by C-H...X (X = F, Cl) intramolecular hydrogen bonding

Aryl-triazole oligomers based on isobutyl 4-fluorobenzoate and isobutyl 4-chlorobenzoate were designed and synthesized. Crystal structure and 1H-1H NOESY experiments demonstrate that the oligomers adopt stable helical conformation, which are induced by C5-H...X-C (X = F, Cl) intramolecular hydrogen bonding between triazole protons and halogen atoms. The stabilities of the folded conformations are confirmed by DFT calculations, which show that each C5-H...F-C planar interaction lowers the energy by ～3 kcal mol-1 on average, and by ～1 kcal mol-1 when C5-H...Cl-C bridges are formed. The hydrogen-bonding networks are disrupted in competitive hydrogen-bonding media such as DMSO, generating the unfolded oligomers.

Design and synthesis of conformationally restricted inhibitors of active thrombin activatable fibrinolysis inhibitor (TAFIa)

A series of 4,5,6,7-tetrahydro-1H-benzimidazole-5-carboxylic acid and 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylic acid derivatives designed as inhibitors of TAFIa has been prepared via a common hydrogenation-alkylation sequence starting from the appropriate benzimidazole and imidazopyridine system. We present a successful design strategy using a conformational restriction approach resulting in potent and selective inhibitors of TAFIa. The X-ray structure of compound 5 in complex with a H333Y/H335Q double mutant TAFI indicate that the conformational restriction is responsible for the observed potency increase.

Cyclization of substitued 2-(2-fluorophenylazo)azines to azino[1, 2-c]benzo[d][1, 2, 4]triazinium derivatives

Light-induced cyclization of several substituted 2-(2-fluorophenylazo) azines in the presence of Ca2+ ions to the corresponding triazinium derivatives is investigated experimentally and computationally. The azo derivatives of 4-methylpyridine 4 undergo facile cyclization to the corresponding triazinium 1, and the rate of cyclization increases with increasing number of fluorine atoms at the benzene ring. No triazinium ions were obtained from azo derivatives of 4-cyanopyridine, pyrazine and pyrimidine, presumably due to their instability under the reaction conditions. The experimental results and mechanism are discussed with the aid of DFT computational results.

A new class of heterogeneous platinum catalysts for the chemoselective hydrogenation of nitroarenes

A new series of nanostructured platinum catalysts able to catalyze the selective reduction of nitroarenes has been developed. The materials, made of organosilica physically doped with nanostructured platinum(0), are stable and efficient. Reactions in general proceed with high yield and often go to completion, while the catalysts can be reused in further reaction runs. This establishes a new class of relevant solid catalysts for synthetic organic chemistry named SiliaCat Platinum-Hydrogel.

BENZIMIDAZOLECARBOXAMIDES AS INHIBITORS OF FAK

This invention relates to benzimadolecarboxamides of formula (I) which are inhibitors of focal adhesion kinase, and as such are useful for treating proliferative diseases

BENZAMIDE FACTOR VIIA INHIBITORS USEFUL AS ANTICOAGULANTS

The present invention provides novel benzamide derivatives of Formula (I): or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein the variables A, W, Y, Z, R8, and R9 are as defined herein. These compounds are selective inhibitors of factor VIIa which can be used as medicaments.

Aminodeoxychorismate synthase inhibitors from one-bead one-compound combinatorial libraries: "Staged" inhibitor design

4-Amino-4-deoxychorismate synthase (ADCS) catalyzes the first step in the conversion of chorismate into p-aminobenzoate, which is incorporated into folic acid. We aim to discover compounds that inhibit ADCS and serve as leads for a new class of antimicrobial compounds. This report presents (1) synthesis of a mass-tag encoded library based on a "staged" design, (2) massively parallel fluorescence-based on-bead screening, (3) rapid structural identification of hits, and (4) full kinetic analysis of ADCS. All inhibitors are competitive against chorismate and Mg2+. The most potent ADCS inhibitor identified has a Ki of 360 μM. We show that the combinatorial diversity elements add substantial binding affinity by interacting with residues outside of but proximal to the active site. The methods presented here constitute a paradigm for inhibitor discovery through active site targeting, enabled by rapid library synthesis, facile massively parallel screening, and straightforward hit identification.

Heterocyclic inhibitors of kinases

The present invention provides compounds of formula I and pharmaceutically acceptable salts thereof. The formula I compounds inhibit the tyrosine kinase activity of growth factor receptors such as VEGFR-2, FGFR-1, thereby making them useful as anti-cancer agents. The formula I compounds are also useful for the treatment of other diseases associated with signal transduction pathways operating through growth factor receptors.