446-26-4

Basic information

• Product Name: 2-FLUORONICOTINIC ACID METHYL ESTER
• Synonyms: 2-FLUORONICOTINIC ACID METHYL ESTER;methyl 2-fluoronicotinate;Methyl 2-fluoropyridine-3-carboxylate;2-fluoronicotin methyl ester;Methyl 2-fluoro-3-pyridinecarboxylate;3-Pyridinecarboxylicacid, 2-fluoro-, methyl ester
• CAS NO: 446-26-4
• Molecular Formula: C₇H₆FNO₂
• Molecular Weight: 155.13
• Product Categories: Pyridine;Pyridines;Esters;Boronic Acid
• Mol File: 446-26-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 22-26 °C
• Boiling Point: 75 °C/5 mmHg
• Flash Point: 110 °C
• Appearance: /
• Density: 1.243g/cm³
• Vapor Pressure: 0.105mmHg at 25°C
• Refractive Index: 1.49
• Storage Temp.: Room temperature.
• PKA: -2.47±0.10(Predicted)
• CAS DataBase Reference: 2-FLUORONICOTINIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUORONICOTINIC ACID METHYL ESTER(446-26-4)
• EPA Substance Registry System: 2-FLUORONICOTINIC ACID METHYL ESTER(446-26-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 446-26-4(Hazardous Substances Data)

Usage

General Description

The chemical 2-Fluoronicotinic acid methyl ester, also known as methyl 2-fluoropyridine-3-carboxylate, is a derivative of nicotinic acid with a methyl group and a fluorine atom attached to the pyridine ring. It is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 2-FLUORONICOTINIC ACID METHYL ESTER is known for its potential applications in medicinal chemistry, especially in the development of new drugs and active pharmaceutical ingredients. Its unique structural and chemical properties make it a valuable building block for the synthesis of various biologically active compounds. However, it is important to handle this chemical with care due to its potential hazards and health risks associated with its use.

InChI:InChI=1/C7H6FNO2/c1-11-7(10)5-3-2-4-9-6(5)8/h2-4H,1H3

Upstream product

• 393-55-5 2-fluoronicotinic acid 
• 77-78-1 dimethyl sulfate 
• 40134-18-7 methyl 2-chloropyridine-3-carboxylate 
• 5345-47-1 2-aminopyridin-3-carboxylic acid 
• 372-48-5 2-fluoropyridine 
• 79-22-1 methyl chloroformate 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 67-56-1 methanol 

Downstream Products

• 112811-90-2 2-benzylsulfanylnicotinic acid 
• 1622217-20-2 methyl 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate 
• 36701-88-9 methyl 2-phenoxypyridine-3-carboxylate 
• 1312356-10-7 4-chloro-1-[(phenylmethyl)oxy]pyrido[2,3-d]pyrimidin-2(1H)-one 
• 1312356-08-3 1-[(phenylmethyl)oxy]pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione 

Relevant articles and documents

Nucleophilic Fluorination of Heteroaryl Chlorides and Aryl Triflates Enabled by Cooperative Catalysis

Aryl and heteroaryl fluorides are growing to be dominant motifs in pharmaceuticals and agrochemicals, yet they are rare in both nature and commodity chemicals. As a consequence, there is an increasingly urgent need to develop mild, cost-effective, and scalable methods for fluorination. The most straightforward route to synthesize aryl fluorides is through the halide exchange "halex"reaction, but conditions, cost, and atom economy preclude most available methods from large-scale manufacturing processes. We report a new approach that leverages the cooperative action of 18-crown-6 ether and tetramethylammonium chloride to catalytically access the reactivity of tetramethylammonium fluoride and achieve halex fluorinations under mild conditions with operational ease. The described methodology readily converts both heteroaryl chlorides and aryl triflates to their corresponding (hetero)aryl fluorides in high yields and purities.

Facile preparation of 3-substituted-2,6-difluoropyridines: Application to the synthesis of 2,3,6-trisubstituted pyridines

We report a facile method for the difluorination of 3-substituted-2,6-dichloropyridines using cesium fluoride as a fluorination reagent in dimethyl sulfoxide. It is proposed that this method for preparing 3-substituted-2,6-difluoropyridines is simpler and easier than those reported in previous literature. To examine the utility of 3-substituted-2,6-difluoropyridines in synthetic chemistry, we also demonstrate a subsequent conversion to 2,3,6-trisubstituted pyridines by a tandem nucleophilic aromatic substitution.

Addition of ester enolates to N-alkyl-2-fluoropyridinium salts: Total synthesis of (±)-20-deoxycamptothecin and (+)-camptothecin

Several 4-substituted dihydropyridones or 2-pyridones have been prepared by nucleophilic addition of α-(methylsulfanyl)ester enolates to N-alkyl-2-fluoropyridinium salts, followed by acid hydrolysis or oxidation with concomitant hydrolysis, of the intermediate 2-fluoro-1,4-dihydropyridine adducts, respectively. Addition of the enolate derived from isopropyl α-(methylsulfanyl)butyrate to N-(quinolylmethyl)-2-fluoropyridinium triflate 21 followed by DDQ treatment gave pyridone 29, from which (±)-20-deoxycamptothecin (31), a known precursor of camptothecin, was synthesized by a radical cyclization-desulfurization, with subsequent elaboration of the lactone E ring by chemoselective reduction. A similar sequence starting from the enolate of a chiral 2-hydroxybutyric acid derivative (33) provides access to natural (+)-camptothecin (37).