2475-81-2

Basic information

• Product Name: methyl 2-amino-4-fluorobenzoate
• Synonyms: methyl 2-amino-4-fluorobenzoate;2-AMino-4-fluoro-benzoic acid Methyl ester;Methyl 4-fluoroanthranilate
• CAS NO: 2475-81-2
• Molecular Formula: C₈H₈FNO₂
• Molecular Weight: 169.154
• Mol File: 2475-81-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 67-68 °C
• Boiling Point: 255.5°C at 760 mmHg
• Flash Point: 108.3°C
• Appearance: /
• Density: 1.264g/cm³
• Vapor Pressure: 0.0163mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: Room temperature.
• PKA: 1.45±0.10(Predicted)
• CAS DataBase Reference: methyl 2-amino-4-fluorobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-amino-4-fluorobenzoate(2475-81-2)
• EPA Substance Registry System: methyl 2-amino-4-fluorobenzoate(2475-81-2)

Safety Data

• Hazardous Substances Data: 2475-81-2(Hazardous Substances Data)

Usage

General Description

Methyl 2-amino-4-fluorobenzoate is a chemical compound with the molecular formula C8H8FNO2. It is a methyl ester of 2-amino-4-fluorobenzoic acid, and it is commonly used in the pharmaceutical industry as an intermediate for the synthesis of various drugs. methyl 2-amino-4-fluorobenzoate is known for its potential pharmacological activities and has been studied for its potential use in the treatment of neurological disorders and cancer. It is important to handle this chemical with proper care and caution, as it may pose health hazards if not handled properly.

InChI:InChI=1/C8H8FNO2/c1-12-8(11)6-3-2-5(9)4-7(6)10/h2-4H,10H2,1H3

Upstream product

• 67-56-1 methanol 
• 321-50-6 7-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione 
• 446-32-2 4-fluoroanthranilic acid 
• 144-55-8 sodium hydrogencarbonate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 623588-40-9 methyl 5-chloro-4-fluoro-2-nitro-benzoate 

Downstream Products

• 791098-86-7 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-fluorobenzoic acid methyl ester 
• 97954-38-6 methyl 4-fluoro-2-(N-methylamino)benzoate 
• 328543-84-6 4-Fluoro-1-(4-hydroxymethyl-phenyl)-8,9-dihydro-7H-2,7,9a-triaza-benzo[cd]azulen-6-one 
• 328547-12-2 methyl 2-bromo-5-fluoro-3-nitrobenzoate 

Relevant articles and documents

Chemoselectivity for Alkene Cleavage by Palladium-Catalyzed Intramolecular Diazo Group Transfer from Azide to Alkene

Alkenes can be cleaved by means of the (3+2) cycloaddition and subsequent cycloreversion of 1,3-dipoles, classically ozone (O3), but the azide (R?N3) variant is rare. Chemoselectivity for these azide to alkene diazo group transfers (DGT) is typically disfavored, thus limiting their synthetic utility. Herein, this work discloses a palladium-catalyzed intramolecular azide to alkene DGT, which grants chemoselectivity over competing aziridination. The data support a catalytic cycloreversion mechanism distinct from other known metal-catalyzed azide/alkene reactions: nitrenoid/metalloradical and (3+2) cycloadditions. Kinetics experiments reveal an unusual mechanistic profile in which the catalyst is not operative during the rate-controlling step, rather, it is active during the product-determining step. Catalytic DGT was used to synthesize N-heterocyclic quinazolinones, a medicinally relevant structural core. We also report on the competing aziridination and subsequent ring expansion to another N-heterocyclic core structure of interest, benzodiazepinones.

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

Tandem C-O and C-N Bonds Formation Through O-Arylation and [3,3]-Rearrangement by Diaryliodonium Salts: Synthesis of N-Aryl Benzo[1,2,3]triazin-4(1H)-one Derivatives

Metal-free O-arylation and [3, 3]-rearrangement have been shown as an efficient strategy to construct new C-O and C-N bonds in one-pot reactions. The method was used to prepare N-aryl benzo[1,2,3]triazin-4(1H)-one derivatives in good yields from N-hydroxy benzo[1,2,3]triazin-4(3H)-one and diaryliodonium salts. The reaction was tolerated a variety of sensitive functional groups such as iodine, nitro, ester, and aldehyde groups. A rational mechanism was proposed based on the experimental results, and the reaction was easily up to gram scale.