210169-05-4

Basic information

• Product Name: 3-AMINO-5-FLUOROPYRIDINE
• Synonyms: 3-AMINO-5-FLUOROPYRIDINE;3-Pyridinamine,5-fluoro-(9CI);3-AMINO-5-FLUOROPYRIDINE 97%;5-Fluoropyridin-3-amine;5-Fluoropyridin-3-ylamine;3-Amine-5-fluoro-pyridin;3-AMine-5-fluoro-pyridine;3-PyridinaMine,5-fluoro-
• CAS NO: 210169-05-4
• Molecular Formula: C₅H₅FN₂
• Molecular Weight: 112.11
• EINECS: -0
• Product Categories: PYRIDINE;AMINEPRIMARY;HALIDE;Pyridine series;Pyridines;Boronic Acid;Building Blocks;C5;C5 to C6;Chemical Synthesis;Fluorinated Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocyclic Fluorinated Building Blocks;Other Fluorinated Heterocycles;Fluorine series
• Mol File: 210169-05-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 86°C
• Boiling Point: 232.7 °C at 760 mmHg
• Flash Point: 94.5 °C
• Appearance: light yellow cryst
• Density: 1.257 g/cm³
• Vapor Pressure: 3.29mmHg at 25°C
• Refractive Index: 1.41
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 3.74±0.20(Predicted)
• CAS DataBase Reference: 3-AMINO-5-FLUOROPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-5-FLUOROPYRIDINE(210169-05-4)
• EPA Substance Registry System: 3-AMINO-5-FLUOROPYRIDINE(210169-05-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 210169-05-4(Hazardous Substances Data)

Usage

Description

3-AMINO-5-FLUOROPYRIDINE is a light yellow crystalline compound that serves as a crucial intermediate in the fields of medicine and organic synthesis. Its unique chemical structure allows it to be utilized in the development of various pharmaceutical compounds, making it a valuable asset in the medical industry.

Uses

Used in Pharmaceutical Industry:
3-AMINO-5-FLUOROPYRIDINE is used as a key intermediate for the synthesis of Ivosidenib, an isocitrate dehydrogenase-1 (IDH1) inhibitor. Ivosidenib is specifically designed to treat acute myeloid leukemia (AML) and cholangiocarcinoma in adults, offering a targeted approach to managing these conditions.
Used in Organic Synthesis:
3-AMINO-5-FLUOROPYRIDINE is also employed as a reactant in the preparation of nonpeptide inhibitors of measles virus entry. This application highlights its versatility in the development of antiviral agents, contributing to the fight against infectious diseases.

Preparation

synthesis of 3-Amino-5-fluoropyridine: A solution of 3-amino-2,4,6-tribromo-5-fluoropyridine (23c) (0.9 g, 2.6 mmol), triethylamine (1.1 cm3, 7.9 mmol), palladium catalyst (0.1 g of 5% Pd-C catalyst) and DCM (15 cm3) was hydrogenated on a Parr apparatus for 18 h. Water (20 cm3) was added and the mixture filtered and extracted into DCM. The DCM solution was dried (MgS04) and evaporated giving 3-amino-5-fluoropyridine (0.3 g, >95% ), m.p. 86 ·c (from DCM) (Found: C, 53.6; H, 4.6; N, 25.0. C5H5FN2 requires C, 53.6; H, 4.5 N, 25.0%);IR spectrum no. 9; mass spectrum no. 5; nmr spectrum no. 29.

InChI:InChI=1/C8H12F3NO/c1-3-12(4-2)6-5-7(13)8(9,10)11/h5-6H,3-4H2,1-2H3/b6-5-

Upstream product

• 82671-06-5 2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid 
• 96568-02-4 2,6-dichloro-5-fluoro-3-nicotinoyl chloride 
• 70-58-6 5-fluoropyridine-3-carboxamide 
• 407-20-5 3-bromo-5-fluoropyridine 
• 342603-20-7 (5-fluoro-3-pyridinyl)carbamic acid 1,1-dimethylethyl ester 
• 30841-93-1 2,4,6-tribromo-3,5-difluoropyridine 
• 700-16-3 Pentafluoropyridine 
• 402-66-4 5-fluoropyridine-3-carboxylic acid 
• 247235-86-5 3-fluoro-5-benzyloxycarbonylaminopyridine 
• 210169-04-3 3-amino-2,4,6-tribromo-5-fluoropyridine 

Downstream Products

• 823218-51-5 5-fluoro-3-iodo-pyridin-2-amine 
• 478909-64-7 benzyl-(5-fluoro-pyridin-3-yl)-amine 
• 1285515-07-2 5-bromo-N-(5-fluoro-3-pyridinyl)-2-[(phenylmethyl)oxy]benzamide 
• 1285515-17-4 N-(5-fluoro-3-pyridinyl)-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide 
• 1196091-23-2 (R)-1-[(5-Fluoro-pyridin-3-ylcarbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane chloride 
• 1338484-90-4 6-bromo-N₁-(5-fluoropyridin-3-yl)benzene-1,2-diamine 
• 1338484-91-5 (S)-tert-butyl 1-(3-bromo-2-(5-fluoropyridin-3-ylamino)phenylamino)-1-oxopropan-2-ylcarbamate 
• 1374969-72-8 tert-butyl (1S,2R)-2-(5-cyano-3-fluoro-6-(5-fluoropyridin-3-ylamino)pyridin-2-ylamino)cyclohexylcarbamate 
• 1393178-59-0 5-fluoro-N-(5-fluoro-2-nitrophenyl)pyridin-3-amine 
• 1393178-60-3 5-fluoro-N₁-(5-fluoropyridin-3-yl)benzene-1,2-diamine 
• 1396084-39-1 4-(2-((5-fluoropyridin-3-yl)amino)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine 
• 1438423-23-4 5-(((1R,2S)-2-aminocyclohexyl)amino)-3-((5-fluoropyridin-3-yl)amino)pyrazine-2-carboxamide 
• 1151802-05-9 7-fluoro-1,5-naphthyridin-4-ol 
• 1437789-80-4 N-((1S,4r)-4-((S)-5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)cyclohexyl)-7-fluoro-1,5-naphthyridine-4-carboxamide 

Relevant articles and documents

Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes

The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).

CHROMENOPYRIDINE DERIVATIVES AS PHOSPHATIDYLINOSITOL PHOSPHATE KINASE INHIBITORS

The invention relates to inhibitors of PI5P4K inhibitors useful in the treatment of cancers, neurodegenerative diseases, inflammatory disorders, and metabolic diseases, having the Formula (I); where A1, A2, G, R1, R2, R3, R4, and W are described herein.

Polyhalogenated heterocyclic compounds. Part 42. Fluorinated nitrogen heterocycles with unusual substitution patterns

Reductive replacement of fluorine in 3,5-dichloro-2,4,6-trifluoropyridine 2a and pentafluoropyridine 2 using DIBAL and LAH leads to useful syntheses of fluoro and chlorofluoro pyridine derivatives. Replacement of fluorine by bromine using a mixture of HBr and AlBr3 is extremely efficient, giving excellent routes to 2,4,6-tribromo-3,5-difluoropyridine 3. Bromofluoro-pyrimidine and -quinoxaline derivatives have also been efficiently synthesised from perfluorinated precursors. Catalytic hydrogenation of bromofluoro heterocycles gives high yields of the corresponding fluorinated heterocycles. Reactions of nucleophiles with 3 gives surprising results. Soft nucleophiles, e.g. PhSNa displace bromine whereas hard nucleophiles, e.g. MeONa, displace fluorine. British Crown Copyright 1998, Defence Evaluation and Research Agency. Published by the Royal Society of Chemistry with the permission of the controller of Her Britannic Majesty's Stationery Office.