4-Aminopyridine supplier | CasNO.504-24-5

Name
4-Aminopyridine
EINECS 207-987-9
CAS No. 504-24-5
Article Data144
CAS DataBase
Density 1.107 g/cm³
Solubility Soluble in water, ethanol, slightly soluble in ethyl ether and benzene, insoluble in light oil and petroleum
Melting Point 157 °C
Formula C₅H₆N₂
Boiling Point 255.2 °C at 760 mmHg
Molecular Weight 94.116
Flash Point 131.8 °C
Transport Information UN 2671 6.1/PG 2
Appearance white to slightly yellow fine crystalline powder
Safety 26-36/37/39-45-60-61
Risk Codes 36/37/38-51/53-23/24/25
Molecular Structure
Hazard Symbols T+,N,Xi
Synonyms Pyridin-4-amine;1H-Pyridin-4-amine;Amino-4 pyridine;gamma-Aminopyridine;p-Aminopyridine;Fampridine;Pyridine, 4-amino-;p-Aminopyridine;Pimadin (free base);
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;

: 1124-33-0
4-nitraminopyridine N-oxide

A: 504-24-5
4-aminopyridine

B: 3535-75-9
4-aminopyridine-1-oxide

Conditions

Conditions	Yield
With cyclohexa-1,4-diene; 5%-palladium/activated carbon In methanol at 120℃; for 0.0833333h; Microwave irradiation;	A 90% B 10%

: 39910-67-3
4-azidopyridine

: 504-24-5
4-aminopyridine

Conditions

Conditions	Yield
With iron In water at 20℃; Inert atmosphere;	88%
With C36H44CuN8(1+)*BF4(1-) In water; toluene at 100℃; for 20h; Sealed tube; chemoselective reaction;	45%
With water for 5h; Inert atmosphere; UV-irradiation; Sealed tube; chemoselective reaction;	44%
With 2,6-di-tert-butyl-4-methyl-phenol In decalin at 153.8℃; Kinetics; Rate constant; Thermodynamic data; Eact, ΔSact; var. temper.; var. conc. of inhibitor;

: 1692-15-5
4-pyridylboronic acid

: 504-24-5
4-aminopyridine

Conditions

Conditions	Yield
With N-Bromosuccinimide; CYANAMID; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 1h; chemoselective reaction;	85%
With N-Bromosuccinimide; N-methoxylamine hydrochloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃;	78%

: 4427-22-9
4-pyridinecarbohydroxamic acid

: 504-24-5
4-aminopyridine

Conditions

Conditions	Yield
In formamide at 130 - 150℃; for 20h;	79%
Stage #1: 4-pyridinecarbohydroxamic acid With potassium carbonate In dimethyl sulfoxide at 90℃; for 3h; Lossen Rearrangement; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; for 1h;

: 19524-06-2
4-bromopyridine hydrochloride

: 504-24-5
4-aminopyridine

Conditions

Conditions	Yield
With bis(triphenylphosphine)nickel(II) chloride; lithium hexamethyldisilazane In toluene at 100℃; for 4h; Glovebox; Sealed tube;	78%

: 1120-87-2
4-bromopyridin

: 504-24-5
4-aminopyridine

Conditions

Conditions	Yield
With ammonium hydroxide; L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate In 1-methyl-pyrrolidin-2-one at 110℃; for 30h;	75%
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 24h;	74%
With ammonia; water at 200℃;

: 626-64-2
pyridin-4-ol

: 504-24-5
4-aminopyridine

Conditions

Conditions	Yield
With sodium tetrahydroborate; 5%-palladium/activated carbon; hydrazine hydrate; lithium hydroxide In 1,4-dioxane at 170℃; for 16h; Molecular sieve; Inert atmosphere;	52%

: 626-61-9
4-Chloropyridine

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 504-24-5
4-aminopyridine

Conditions

Conditions	Yield
for 6h; Reflux; neat (no solvent);	51%

: 2-(1,3-dithian-2-yl)propan-2-yl (pyridin-4-yl)carbamate

: 504-24-5
4-aminopyridine

Conditions

Conditions	Yield
Stage #1: 2-(1,3-dithian-2-yl)propan-2-yl (pyridin-4-yl)carbamate With sodium periodate In tetrahydrofuran; water at 20℃; for 12h; Inert atmosphere; Schlenk technique; Stage #2: With potassium carbonate In methanol at 20℃; for 1h; Inert atmosphere; Schlenk technique;	48%

: 1135-35-9
cyclohexanone-[4]pyridylhydrazone

: 141-52-6
sodium ethanolate

A: 504-24-5
4-aminopyridine

B: 4329-69-5
6,7,8,9-tetrahydro-5H-pyrido[4,3-b]indole

C: 35036-85-2
N-ethylpyridine-4-amine

Conditions

Conditions	Yield
In diethylene glycol at 235 - 240℃; for 0.25h;	A 15% B 39% C 37%

...Expand

: 1135-35-9
cyclohexanone-[4]pyridylhydrazone

A: 504-24-5
4-aminopyridine

B: 4329-69-5
6,7,8,9-tetrahydro-5H-pyrido[4,3-b]indole

C: 35036-85-2
N-ethylpyridine-4-amine

Conditions

Conditions	Yield
With sodium ethanolate In diethylene glycol at 235 - 240℃; for 0.25h;	A 15% B 39% C 37%
With sodium ethanolate In diethylene glycol at 235 - 240℃; for 0.25h; Rate constant; Product distribution; other solvent, various concentrations of sodium ethoxide;	A 15% B 39% C 37%

...Expand

: 2569-58-6, 54772-94-0, 54773-16-9
(E)-4-phenylazopyridine

A: 504-24-5
4-aminopyridine

B: 123-30-8
4-amino-phenol

C: 20815-66-1
4-(2-(pyridin-4-yl)diazenyl)phenol

D: N-Phenyl-N'-{1-[4-(pyridin-4-ylazo)-phenyl]-1H-pyridin-4-ylidene}-hydrazine

Conditions

Conditions	Yield
With sulfuric acid Product distribution; Rate constant; reaction of phenylazopyridines with aq. H2SO4; reaction intermediates, kinetics and mechanism; effect of H2SO4 concentration of product ratio and reaction rate; UV study;	A 19% B 20% C 22% D 31%
With sulfuric acid	A 19% B 20% C 22% D 31%

...Expand

: N-Ethylidenasparaginsaeuredinitril

A: 504-24-5
4-aminopyridine

B: 110-61-2
butanedinitrile

C: 2-Eth-(E)-ylideneamino-acrylonitrile

D: (Z)-2-Methyl-3-azahex-4-endinitril

E: (E)-2-Methyl-3-azahex-4-endinitril

Conditions

Conditions	Yield
With 4 A molecular sieve at 500℃; under 0.1 Torr; Product distribution; flash vaccum pyrolysis;	A 26.1% B n/a C n/a D n/a E n/a

...Expand

: N-Ethylidenasparaginsaeuredinitril

A: 504-24-5
4-aminopyridine

B: 110-61-2
butanedinitrile

C: (Z)-2-Methyl-3-azahex-4-endinitril

D: (E)-2-Methyl-3-azahex-4-endinitril

Conditions

Conditions	Yield
With 4 A molecular sieve at 500℃; under 0.1 Torr; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;	A 26.1% B n/a C n/a D n/a

...Expand

: 51790-32-0
4-(N'-Pyridin-4-yl-hydrazino)-phenol

A: 504-24-5
4-aminopyridine

B: 123-30-8
4-amino-phenol

C: 20815-66-1
4-(2-(pyridin-4-yl)diazenyl)phenol

Conditions

Conditions	Yield
With sulfuric acid	A 22% B 24% C 26%
With sulfuric acid Product distribution; Rate constant; reaction of phenylazopyridines with aq. H2SO4; reaction intermediates, kinetics and mechanism; effect of H2SO4 concentration of product ratio and reaction rate; UV study;	A 22% B 24% C 26%
With sulfuric acid Product distribution; Rate constant; acid-catalysed disproportionation and benzidine rearrangement of phenylhydrazinopyridines; reaction pathways; kinetics and mechanism;	A 22% B 24% C 26%

...Expand

: 20815-53-6
4-(4-chlorophenylazo)pyridine

A: 504-24-5
4-aminopyridine

B: 4-(2,4-dichlorophenylazo)pyridine

C: 3-chloro-4-[4]pyridylazo-phenol

D: 17609-80-2
4-amino-3-chlorophenol

E: 554-00-7
2,4-Dichloroaniline

F: 253333-13-0
(E)-4-(pyridin-4-yldiazenyl)phenol

Conditions

Conditions	Yield
With sulfuric acid Rate constant; Product distribution; var. conc. of acid;	A 26% B 13% C 15% D 14% E 10% F 2%

...Expand

: 4-(4-chlorophenylhydrazo)pyridine hydrochloride

A: 504-24-5
4-aminopyridine

B: 4-(2,4-dichlorophenylazo)pyridine

C: 554-00-7
2,4-Dichloroaniline

D: 106-47-8
4-chloro-aniline

E: N-(4-chloro-phenyl)-N'-{1-[4-(pyridin-4-ylazo)-phenyl]-1H-pyridin-4-ylidene}-hydrazine

F: 20815-53-6
4-(4-chlorophenylazo)pyridine

Conditions

Conditions	Yield
With sulfuric acid for 24h; Rate constant; Mechanism; Product distribution; var. conc. of acid; var. time; other (arylazo)pyridine;	A 25% B 21% C 20% D 3% E n/a F 5%

...Expand

: 72109-70-7
4-(2-phenylhydrazin)pyridine

A: 504-24-5
4-aminopyridine

B: 123-30-8
4-amino-phenol

C: 60172-08-9
N1-(4-pyridinyl)-1,4-benzenediamine

D: 20815-66-1
4-(2-(pyridin-4-yl)diazenyl)phenol

E: 2569-58-6, 54772-94-0, 54773-16-9
(E)-4-phenylazopyridine

F: 62-53-3
aniline

Conditions

Conditions	Yield
With sulfuric acid Product distribution; Rate constant; acid-catalysed disproportionation and benzidine rearrangement of phenylhydrazinopyridines; reaction pathways; kinetics and mechanism;	A 15% B 7% C 6% D 5% E 9% F 8%

...Expand

: 72109-70-7
4-(2-phenylhydrazin)pyridine

A: 504-24-5
4-aminopyridine

B: 60172-08-9
N1-(4-pyridinyl)-1,4-benzenediamine

C: 2569-58-6, 54772-94-0, 54773-16-9
(E)-4-phenylazopyridine

D: 62-53-3
aniline

Conditions

Conditions	Yield
With sulfuric acid Further byproducts given;	A 15% B 6% C 9% D 8%

...Expand

: 504-24-5
4-aminopyridine

: 1943-83-5
2-chloroethyl isothiocyanate

: 62491-96-7
N-(2-chloroacetyl)-N'-(4-pyridyl)urea

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	100%
In toluene at 0 - 12℃; for 12h;	94%
In toluene at 20℃; for 6h;	87%

: 504-24-5
4-aminopyridine

: 24424-99-5
di-tert-butyl dicarbonate

: 98400-69-2
N-(4-pyridyl) t-butyl carbamate

Conditions

Conditions	Yield
copper(II) bis(tetrafluoroborate) at 30 - 35℃; for 0.5h;	100%
With perchloric acid at 30 - 35℃; for 0.25h;	100%
In PEG-400 at 20℃; for 0.25h;	100%

: 864950-69-6
methanesulfonic acid 3-(2-phenylethynyl-phenyl)-prop-2-ynyl ester

: 504-24-5
4-aminopyridine

: 4-amino-1-[3-(2-phenylethynyl-phenyl)-prop-2-ynyl]-pyridinium; methanesulfonate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 24h;	100%

: 504-24-5
4-aminopyridine

: 1523-15-5
2,4-dinitrophenyl benzoate

: C18H14N4O6

Conditions

Conditions	Yield
In water; dimethyl sulfoxide at 25℃; Kinetics;	100%

: 504-24-5
4-aminopyridine

: 2176-62-7
2,3,4,5,6-pentachloropyridine

: 1,1',1''-tris[4-amino-(3,5-dichloropyridine-2,4,6-triyl)-pyridinium] trichloride

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 1h;	100%
Heating;

: 504-24-5
4-aminopyridine

: 3344-70-5
1,12-dibromododecane

: 1,12-bis(4-aminopyridinio)dodecane dibromide

Conditions

Conditions	Yield
In various solvent(s) for 24h; Heating;	100%

: 504-24-5
4-aminopyridine

: 627906-79-0
4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methylbenzoyl chloride

: 4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methyl-N-(4-pyridinyl)benzamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 5h;	100%

: 504-24-5
4-aminopyridine

: bis(4-aminopyridinium) hexafluorosilicate

Conditions

Conditions	Yield
With fluorosilicic acid In methanol	100%

: 504-24-5
4-aminopyridine

4-nitrobenzoic acid ester: 4-nitrobenzoic acid ester

: 13160-58-2
4-nitro-N-(pyridin-4-yl)benzamide

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 0.0333333h; Flow reactor;	100%

: 504-24-5
4-aminopyridine

: 3-[3-methyl-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]benzoic acid

: 3-[3-methyl-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-N-(4-pyridyl)benzamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	100%
With N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	100%

: 504-24-5
4-aminopyridine

: 762-70-9
2-chloroethanesulfonyl fluoride

: C7H10FN2O2S(1+)*Cl(1-)

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 0.0833333h; Menshutkin Reaction;	100%

: 504-24-5
4-aminopyridine

: 583-55-1
1-Bromo-2-iodobenzene

: 86775-99-7
N-(2-bromophenyl)pyridin-4-amine

Conditions

Conditions	Yield
With sodium t-butanolate; 1,1'-bis-(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)dipalladium (0) In toluene at 115℃; for 18h;	99.9%
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 120℃; for 18h; Sealed tube;	99%
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃; for 14h; Cross-coupling;	96%

: 504-24-5
4-aminopyridine

: 74-88-4
methyl iodide

: 7680-59-3
N-methyl-4-aminopyridinium iodide

Conditions

Conditions	Yield
for 8h;	99%
In ethyl acetate
In diethyl ether at 20℃;
In acetonitrile at 80℃;

: 504-24-5
4-aminopyridine

: 181823-46-1
2-(2-Dimethylamino-benzylsulfanyl)-nicotinic acid

: 181822-33-3
2-(2-Dimethylamino-benzylsulfanyl)-N-pyridin-4-yl-nicotinamide

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 3h; Ambient temperature;	99%

: 504-24-5
4-aminopyridine

: 108-31-6
maleic anhydride

: maleic acid 4-pyridylmonoamide

Conditions

Conditions	Yield
In 1,4-dioxane at 20℃;	99%
In tetrahydrofuran at 25℃; for 3h;	78.6%

: 504-24-5
4-aminopyridine

: 201230-82-2
carbon monoxide

: 8-[(2E)-3-(2-iodophenyl)prop-2-enoyl]-1,4-dioxa-8-azaspiro[4.5]decane

: 3-[2-(1,4-dioxa-8-azaspiro[4,5]dec-8-yl)-2-oxoethyl]-2-pyridin-4-ylisoindolin-1-one

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); trifuran-2-yl-phosphane; caesium carbonate In toluene at 90℃; under 760 Torr; for 18h; Michael addition;	99%

...Expand

: 865094-47-9
isopropenyl (5-tert-butyl-2-(p-tolyl)-2H-pyrazol-3-yl)carbamate

: 504-24-5
4-aminopyridine

: N-(5-tert-butyl-2-(p-tolyl)-2H-pyrazol-3-yl)-N'-(pyridin-4-yl)urea

Conditions

Conditions	Yield
With 1-Methylpyrrolidine In tetrahydrofuran at 55℃; for 0.5h;	99%

: (E)-1-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-3-(2-iodo-phenyl)-propenone

: 504-24-5
4-aminopyridine

: 201230-82-2
carbon monoxide

: 3-[2-(1,4-dioxa-8-azaspiro[4,5]dec-8-yl)-2-oxoethyl]-2-pyridin-4-ylisoindolin-1-one

Conditions

Conditions	Yield
With trifuran-2-yl-phosphane; caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 90℃; for 18h;	99%

...Expand

: 504-24-5
4-aminopyridine

: 24424-99-5
di-tert-butyl dicarbonate

: 75-65-0
tert-butyl alcohol

: 98400-69-2
N-(4-pyridyl) t-butyl carbamate

Conditions

Conditions	Yield
With potassium hydroxide In water	99%

...Expand

: 504-24-5
4-aminopyridine

: ammonium hexafluorophosphate

: Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(H2O)2(2+)*2PF6(1-)=[Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(H2O)2](PF6)2

: Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(H2NC5H4N)2(2+)*2PF6(1-)=[Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(H2NC5H4N)2](PF6)2

Conditions

Conditions	Yield
In methanol N2; Co comp. dissolved under reflux, to a soln. added an excess of ligand, refluxed for 25 min, a soln. of NH4PF6 added; ppt. filtered, washed copiously (diethyl ether), dried (vac.); elem. anal.;	99%

...Expand

: 504-24-5
4-aminopyridine

: 736141-91-6, 195193-91-0
trans-bis[O-methyl-(4-methoxyphenyl)phosphonodithioato]nickel

: 377737-43-4
[Ni(O-methyl-(4-methoxyphenyl)phosphonodithioato)2(p-aminopyridine)2]

Conditions

Conditions	Yield
In methanol; dichloromethane excess of pyridine deriv. in MeOH was added dropwise to soln. of Ni complex in CH2Cl2, slow evapn. of mixt. at room temp.; elem. anal.;	99%

: 504-24-5
4-aminopyridine

: Cu(C6H5C5H2N(C5H3NN(CH3)NCH)2)(H2O)2(2+)*2PF6(1-)=[Cu(C6H5C5H2N(C5H3NN(CH3)NCH)2)(H2O)2](PF6)2

: [Cu(PhC5H2N(C5H3NN(CH3)NCH)2)(aminopyridine)](PF6)2

Conditions

Conditions	Yield
In methanol excess of N-compd. was added to hot MeOH soln. of Cu-complex, reflux for25 min, concd. MeOH soln. of NH4PF6 was added; ppt. was collected, washed with copious amt. of Et2O, dried in vac., elem. anal.;	99%

: 504-24-5
4-aminopyridine

: 100-51-6
benzyl alcohol

: 13556-71-3
N-benzyl-4-aminopyridine

Conditions

Conditions	Yield
With iron(II,III) oxide; potassium tert-butylate In 1,4-dioxane at 90℃; for 168h; Inert atmosphere;	99%
With cesium hydroxide; (sat-NHC-Bn)Ir(CO)(PPh3)Cl at 100℃; for 24h; Inert atmosphere;	99%
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 48h;	99%

: 504-24-5
4-aminopyridine

: 779355-57-6
(pyridine)2Ni{CH2CH2C(=O)O}

: 1232169-66-2
[Ni(4-aminopyridine)2(C2H4COO)]

Conditions

Conditions	Yield
In N,N-dimethyl-formamide byproducts: py; Ar; DMF soln. of Ni compd. (2.04 mmol) treated with ligand (4.14 mmol), mixt. stirred for 30 min; evapd., elem. anal.;	99%

: 504-24-5
4-aminopyridine

: 495-76-1
piperonol

: 1301628-37-4
N-(benzo[d][1,3]dioxol-5-ylmethyl)pyridin-4-amine

Conditions

Conditions	Yield
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 48h; Inert atmosphere;	99%
With cesium hydroxide; palladium diacetate In toluene at 150℃; for 12h;	99%

: 504-24-5
4-aminopyridine

: 499-80-9
pyridine-2,4-dicarboxylic acid

: N-(pyridin-4-yl)isonicotinamide

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	99%

: 504-24-5
4-aminopyridine

: 74-96-4
ethyl bromide

: 60041-10-3
4-amino-1-ethylpyridinium bromide

Conditions

Conditions	Yield
In acetone for 16h; Inert atmosphere; Schlenk technique;	99%
In acetone at 20℃; for 12h;	95%

: 504-24-5
4-aminopyridine

: 371-92-6
1,1,1-trifluoro-2-isocyanatoethane

: 1-(pyridin-4-yl)-3-(2,2,2-trifluoroethyl)urea

Conditions

Conditions	Yield
at 20℃;	99%

: 504-24-5
4-aminopyridine

: 2489-52-3
3-(chlorosulfonyl)benzenesulfonyl fluoride

: 3-(N-(pyridin-4-yl)sulfamoyl)benzene-1-sulfonyl fluoride

Conditions

Conditions	Yield
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction;	99%

: 504-24-5
4-aminopyridine

: 4-(chlorosulfonyl)benzenesulfonyl fluoride

: C11H9FN2O4S2

Conditions

Conditions	Yield
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction;	99%

4-Aminopyridine Consensus Reports

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

4-Aminopyridine Standards and Recommendations

DOT Classification: 6.1; Label: Poison

4-Aminopyridine 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.

Product Name

4-Aminopyridine

Synthetic route

4-Aminopyridine Consensus Reports

4-Aminopyridine Standards and Recommendations

4-Aminopyridine Specification

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