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504-24-5

Basic Information
CAS No.: 504-24-5
Name: 4-Aminopyridine
Article Data: 144
Cas Database
Molecular Structure:
Molecular Structure of 504-24-5 (4-Aminopyridine)
Formula: C5H6N2
Molecular Weight: 94.116
Synonyms: Pyridin-4-amine;1H-Pyridin-4-amine;Amino-4 pyridine;gamma-Aminopyridine;p-Aminopyridine;Fampridine;Pyridine, 4-amino-;p-Aminopyridine;Pimadin (free base);
EINECS: 207-987-9
Density: 1.107 g/cm3
Melting Point: 157 °C
Boiling Point: 255.2 °C at 760 mmHg
Flash Point: 131.8 °C
Solubility: Soluble in water, ethanol, slightly soluble in ethyl ether and benzene, insoluble in light oil and petroleum
Appearance: white to slightly yellow fine crystalline powder
Hazard Symbols: VeryT+,DangerousN,IrritantXi
Risk Codes: 36/37/38-51/53-23/24/25
Safety: 26-36/37/39-45-60-61
Transport Information: UN 2671 6.1/PG 2
PSA: 38.91000
LogP: 1.24500
Synthetic route
98400-69-2

N-(4-pyridyl) t-butyl carbamate

504-24-5

4-aminopyridine

Conditions
ConditionsYield
With nitric acid In dichloromethane at 0℃; for 2h;97%
1122-61-8

4-nitropyridine

504-24-5

4-aminopyridine

Conditions
ConditionsYield
With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; chemoselective reaction;97%
With hydrogen In water at 25℃; for 15h; Green chemistry; chemoselective reaction;94%
With triethylamine In water at 80℃; for 6h; Reagent/catalyst; Solvent; Inert atmosphere; Green chemistry; chemoselective reaction;92%
15854-87-2

4-iodopyridine

504-24-5

4-aminopyridine

Conditions
ConditionsYield
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; liquid NH3;97%
626-61-9

4-Chloropyridine

504-24-5

4-aminopyridine

Conditions
ConditionsYield
With ammonia; copper dichloride at 65℃; for 8h; Temperature; Autoclave; Inert atmosphere;96.7%
With ammonia; zinc(II) chloride at 220 - 230℃; im Rohr;
Multi-step reaction with 2 steps
1: 2 h / Heating
2: CH3SO2OH / 10percent Pd-C / ethanol / Heating
View Scheme
1453-82-3

isonicotinamide

504-24-5

4-aminopyridine

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; N-ethyl-N,N-diisopropylamine In water; acetonitrile at 30℃; for 4h; Solvent;96%
With sodium hypochlorite; sodium hydroxide at 0 - 10℃;91.8%
With potassium hydroxide; bromine at 70℃;
With chlorine; sodium hydroxide In water at -5 - 5℃; Product distribution / selectivity;
1124-33-0

4-nitraminopyridine N-oxide

504-24-5

4-aminopyridine

Conditions
ConditionsYield
With titanium tetrachloride; tin(ll) chloride In tetrahydrofuran for 0.5h; Ambient temperature;95%
With palladium 10% on activated carbon; ammonium formate In ethanol at 20℃; for 16h;94%
With sodium hypophosphite; palladium on activated charcoal In acetic acid at 60℃; for 2.5h;92%
13556-71-3

N-benzyl-4-aminopyridine

504-24-5

4-aminopyridine

Conditions
ConditionsYield
With ammonium formate; zinc In ethylene glycol for 0.0416667h; microwave irradiation;95%
With ammonium formate; magnesium In ethylene glycol for 0.025h; microwave irradiation;95%
With sulfuric acid for 24h; Ambient temperature;78%
100-48-1

pyridine-4-carbonitrile

504-24-5

4-aminopyridine

Conditions
ConditionsYield
With sodium hypochlorite; sodium hydroxide In water at 40 - 70℃; for 1h; Product distribution / selectivity;90.8%
With sodium hypochlorite; sodium hydroxide In water at 40 - 70℃; for 1h; Product distribution / selectivity;90.8%
With sodium hypochlorite; sodium pertungstate In water at 0 - 95℃; for 12h; Temperature;

3,5-dibromopiperidin-4-one

504-24-5

4-aminopyridine

Conditions
ConditionsYield
With ammonium hydroxide In dichloromethane at 40 - 45℃; for 4h;90.6%
3535-75-9

4-aminopyridine-1-oxide

504-24-5

4-aminopyridine

Conditions
ConditionsYield
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 0 - 35℃; for 0.25h; Reduction;90%
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran at 35℃; for 0.5h; Reduction;90%
With palladium on activated charcoal; ethanol Hydrogenation;
With methanol; nickel Hydrogenation;
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Consensus Reports

Reported in EPA TSCA Inventory. EPA Extremely Hazardous Substances List.

Standards and Recommendations

DOT Classification:  6.1; Label: Poison

Specification

The 4-Aminopyridine, with the CAS registry number 504-24-5, is also known as Dalfampridine. 4-Aminopyridine is an organic compound with the chemical formula C5H4N–NH2. It belongs to the product categories of Pyridine; Organics; Amines; Pyridines; Pyridines derivates; Heterocyclic Compounds; Alphabetical Listings; Stable Isotopes; Potassium channel; Ion Channels. Its EINECS number is 207-987-9 and molecular weight is 94.11. What's more, its systematic name is pyridin-4-amine. It should be sealed and stored in a dry place. Moreover, it should be protected from light. It is one of the potassium channel blockers, with secondary effect on calcium currents, which is used mainly as a research tool and to characterize channel subtypes. It is used in organic synthesis.

Physical properties of 4-Aminopyridine are: (1)ACD/LogP: 0.26; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.22; (4)ACD/LogD (pH 7.4): -1.51; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 16.13 Å2; (13)Index of Refraction: 1.587; (14)Molar Refractivity: 28.58 cm3; (15)Molar Volume: 84.9 cm3; (16)Polarizability: 11.33×10-24cm3; (17)Surface Tension: 51.2 dyne/cm; (18)Density: 1.107 g/cm3; (19)Flash Point: 131.8 °C; (20)Enthalpy of Vaporization: 49.27 kJ/mol; (21)Boiling Point: 255.2 °C at 760 mmHg; (22)Vapour Pressure: 0.0165 mmHg at 25°C.

Preparation of  4-Aminopyridine: this chemical can be prepared by 4-nitro-pyridine-1-oxide at the ambient temperature. This reaction will need reagents TiCl4, SnCl2 and solvent tetrahydrofuran with the reaction time of 30 min. The yield is about 95%.

4-Aminopyridine can be prepared by 4-nitro-pyridine-1-oxide at the ambient temperature

Uses of 4-Aminopyridine: it can be used to produce N-pyridin-4-yl-benzamide at the temperature of 60 °C. It will need reagent triethylamine and solvent 1,2-dichloro-ethane with the reaction time of 3 hours. The yield is about 73%.

4-Aminopyridine can be used to produce N-pyridin-4-yl-benzamide at the temperature of 60 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic by inhalation, in contact with skin and if swallowed. It is toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible). This material and its container must be disposed of as hazardous waste. You should avoid releasing it to the environment just refering to special instructions/safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: n1ccc(N)cc1
(2)Std. InChI: InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)
(3)Std. InChIKey: NUKYPUAOHBNCPY-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 2370ug/kg (2.37mg/kg)   ASTM Special Technical Publication. Vol. (680), Pg. 157, 1979.
dog LD50 oral 3700mg/kg (3700mg/kg)   Toxicology and Applied Pharmacology. Vol. 26, Pg. 532, 1973.
 
duck LD50 oral 4200mg/kg (4200mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
 
man LDLo oral 590ug/kg (.59mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Clinical Toxicology. Vol. 16, Pg. 487, 1980.
 
mouse LD50 intracrebral 4mg/kg (4mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Australian Journal of Experimental Biology and Medical Science. Vol. 36, Pg. 365, 1958.
 
mouse LD50 intraperitoneal 10mg/kg (10mg/kg)   Journal of Medicinal Chemistry. Vol. 8, Pg. 296, 1965.
mouse LD50 intravenous 7mg/kg (7mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Annales Pharmaceutiques Francaises. Vol. 26, Pg. 345, 1968.
 
mouse LD50 oral 19mg/kg (19mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(9-10), Pg. 64, 1992.
mouse LDLo subcutaneous 5mg/kg (5mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 226, Pg. 163, 1955.
 
pigeon LD50 oral 6mg/kg (6mg/kg)   Journal of Wildlife Management. Vol. 29, Pg. 830, 1965.
quail LD50 oral 7650ug/kg (7.65mg/kg)   ASTM Special Technical Publication. Vol. (680), Pg. 157, 1979.
rabbit LD50 intravenous 5500ug/kg (5.5mg/kg)   Eksperimentalna Meditsina i Morfologiya. Vol. 11, Pg. 162, 1972.
 
rat LD50 intraperitoneal 6500ug/kg (6.5mg/kg)   Toxicology and Applied Pharmacology. Vol. 26, Pg. 532, 1973.
 
rat LD50 oral 21mg/kg (21mg/kg)   Journal de Toxicologie Clinique et Experimentale. Vol. 6(3), Pg. 175, 1986.
rat LD50 subcutaneous 19mg/kg (19mg/kg)   Eksperimentalna Meditsina i Morfologiya. Vol. 11, Pg. 162, 1972.
 
women TDLo oral 120ug/kg (.12mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 583, 1994.