4-Aminopyridine

Base Information

• Chemical Name: 4-Aminopyridine
• CAS No.: 504-24-5
• Molecular Formula: C5H6N2
• Molecular Weight: 94.116
• Hs Code.: 2933.39
• European Community (EC) Number: 207-987-9,635-582-0
• NSC Number: 757845,15041
• UN Number: 2671
• UNII: BH3B64OKL9
• DSSTox Substance ID: DTXSID0023870
• Nikkaji Number: J1.568G,J270.956B
• Wikipedia: 4-Aminopyridine
• Wikidata: Q372539
• NCI Thesaurus Code: C76777
• RXCUI: 897018
• Pharos Ligand ID: M5RAU2PYY1GR
• Metabolomics Workbench ID: 54974
• ChEMBL ID: CHEMBL284348
• Mol file: 504-24-5.mol

Synonyms:4 Aminopyridine;4 Aminopyridine Sustained Release;4-Aminopyridine;4-Aminopyridine Sustained Release;Dalfampridine;Fampridine SR;Fampridine-SR;Pymadine;Sustained Release, 4-Aminopyridine;VMI 103;VMI-103;VMI103

Chemical Property of 4-Aminopyridine

Chemical Property:

• Appearance/Colour: white to slightly yellow fine crystalline powder
• Vapor Pressure: 0.0165mmHg at 25°C
• Melting Point: 157 °C
• Refractive Index: 1.5560 (estimate)
• Boiling Point: 255.2 °C at 760 mmHg
• PKA: 9.114(at 25℃)
• Flash Point: 131.8 °C
• PSA: 38.91000
• Density: 1.107 g/cm³
• LogP: 1.24500
• Storage Temp.: 0-6°C
• Solubility.: H2O: soluble50mg/mL, clear, colorless
• Water Solubility.: Soluble in water(112 g/L at 20 deg C). Soluble in ethyl ether, benzene. Slightly soluble in ligroin. Very soluble in ethanol. So
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 94.053098200
• Heavy Atom Count: 7
• Complexity: 48
• Transport DOT Label: Poison

Purity/Quality:

99%, ^*data from raw suppliers

4-Aminopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N,Xi
• Hazard Codes: T+,N,T,Xi
• Statements: 28-36/37/38-51/53-23/24/25
• Safety Statements: 26-36/37/39-45-60-61-37/39-28A-1

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Avicides
• Drug Classes: Multiple Sclerosis Agents
• Canonical SMILES: C1=CN=CC=C1N
• Recent ClinicalTrials: Effect of Dalfampridine in Patients With Hereditary Spastic Paraplegia
• Recent EU Clinical Trials: Clemastine fumarate as remyelinating treatment in internuclear ophthalmoparesis and multiple sclerosis
• General Description: 4-Aminopyridine, also known as fampridine or p-aminopyridine, is a pyridine derivative with an amino group at the 4-position. 4-Aminopyridine serves as a key substrate in nucleophilic aromatic substitution reactions, where it can undergo rearrangement to form pyridin-4-yl α-substituted acetamides, particularly when reacted with acyl chlorides and triethylamine. The presence of electron-withdrawing halides at the 3-position enhances its reactivity in such transformations, making it a versatile intermediate for synthesizing functionalized molecules with potential biological relevance.

Technology Process of 4-Aminopyridine

There total 99 articles about 4-Aminopyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

4-nitropyridine (1122-61-8) → 4-aminopyridine (504-24-5)

Guidance literature:

With C₃₆H₅₆Cl₃CrN₂O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; at 60 ℃; for 24h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jacs.0c12318

Reference yield: 97.0%

N-(4-pyridyl) t-butyl carbamate (98400-69-2) → 4-aminopyridine (504-24-5)

Guidance literature:

With nitric acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)00900-0

Reference yield: 97.0%

4-iodopyridine (15854-87-2) → 4-aminopyridine (504-24-5)

Guidance literature:

With copper(l) iodide; ascorbic acid; In ammonia; at 25 ℃; for 18h; liquid NH₃;

DOI:10.1021/jo301204t

upstream raw materials:

pyridine

4-Chloropyridine

4-aminopyridine-1-oxide

triphenyl phosphite

Downstream raw materials:

1,3-bis(pyridin-4-yl)urea

N-(pyridin-4-yl)pyridine-3-carboxamide

4-(Methylamino)pyridine

dmap

Refernces

Rearrangement of 4-amino-3-halo-pyridines by nucleophilic aromatic substitution

10.1021/jo4003773

The study investigates the rearrangement of 3-halo-4-aminopyridines through nucleophilic aromatic substitution, resulting in the formation of pyridin-4-yl α-substituted acetamides. The key chemicals involved are 3-halo-4-aminopyridines, which act as the substrates, and acyl chlorides and triethylamine, which serve as reagents. The reaction involves the in situ generation of a ketene intermediate from the acyl chloride by dehydrohalogenation with triethylamine. This intermediate then reacts with the amine nitrogen of the 4-aminopyridine substrate, leading to an intramolecular nucleophilic attack and the formation of a new C-C bond, effectively inserting a two-carbon unit into the C-N bond of the starting material. The study explores various substituted 4-aminopyridines and different acyl chlorides, finding that electron-withdrawing halides in the 3-position of the pyridine ring facilitate the reaction, while other substituents like nitrile or methyl ester groups do not support the rearrangement. The resulting pyridin-4-yl α-substituted acetamides are synthetically useful products with potential applications in the synthesis of functionalized molecules and future biological screening campaigns.

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