CAS No.504-24-5,4-Aminopyridine Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	504-24-5
Name:	4-Aminopyridine
Article Data:	144

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:	T+,N,Xi
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

Conditions	Yield
With nitric acid In dichloromethane at 0℃; for 2h;	97%

: 1122-61-8
4-nitropyridine

: 504-24-5
4-aminopyridine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

Raw Materials

141-97-9

626-64-2

67-56-1

Downstream Products

694-52-0

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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.