Welcome to LookChem.com Sign In|Join Free

CAS

  • or

504-24-5

Post Buying Request

504-24-5 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

504-24-5 Usage

Description

4-Aminopyridine (4-AP, fampridine, dalfampridine) is the first drug approved by the FDA to improve walking in patients with multiple sclerosis (MS). Dalfampridine is a voltage-gated potassium channel blocker that readily penetrates the CNS and increases the conduction and duration of action potential across nerve fibers resulting in enhanced functionality as observed in the walking speed of MS patients.From a safety perspective, seizure was the most important adverse event from various dalfampridine clinical trials. Therefore, dalfampridine is contraindicated in patients with a history of seizures. Since dalfampridine is primarily excreted by the kidney as unchanged drug, it is also contraindicated in patients with moderate to severe renal impairment. Assessing the overall benefit–risk profile from various clinical trials, the FDA approved dalfampridine (daily oral dose of 10 mg, b.i.d.) to improve walking in MS patients with existing gait impairment.

Chemical Properties

4-aminopyridine is a white crystalline solid that contains about 98% active ingredient. It is soluble in water and slightly soluble in benzene and ether. 4-Aminopyridine formulations are classifi ed by the US Environmental Protection Agency (US EPA) as restricted use pesticides (RUPs) and therefore should be purchased and used only by certifi ed and trained workers and applicators. Avitrol is available as grain baits or as a powder concentrate. It is one of the most prominent avicides. It is registered with the EPA for use against red-winged blackbirds, blackbirds in agricultural fi elds, grackles, pigeons, and sparrows around public buildings, and various birds around livestock feeding pens. Avitrol repels birds by poisoning a few members of a fl ock, causing them to become hyperactive.

Originator

Rush University Medical Center (United States)

Uses

Different sources of media describe the Uses of 504-24-5 differently. You can refer to the following data:
1. Avitrol (4-aminopyridine), has repellent–toxicant properties for birds and is classed as a severe poison and irritant. This secondary bird repellent can be used as a broadcast bait, causing uncoordinated flight and distress calls and escape responses in nearby birds.
2. Dalfampridine is used in characterizing subtypes of potassium channel, and has also been used to manage some of the symptoms of multiple sclerosis, and is indicated for symptomatic improvement of walking in adults with several variations of the disease. Dalfampridine is a precursor to the drug Pinacidil.

Definition

ChEBI: 4-aminopyridine is an aromatic amine that is pyridine bearing a single amino substituent at position 4. An orphan drug in the US, it is used to improve walking in adults with multiple sclerosis. It has a role as an avicide, a potassium channel blocker and an orphan drug. It is an aromatic amine and an aminopyridine.

Brand name

Neurelan (E′lan);Ampyra.

General Description

White crystalline material with no odor. Used as an avicide, an intermediate and as a fixer for some textile dyes.

Reactivity Profile

4-Aminopyridine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

4-Aminopyridine, a pyridine compound, is an extremely effective bird poison. In agriculture, 4-AP is used as an extremely effective bird poison sold under the brand name Avitrol. It is highly toxic to all mammals including humans if dosages are exceeded, and as an experimental drug, the recommended dose data is unavailable.

Fire Hazard

Material may produce irritating or poisonous gases in fire. Runoff from fire control water may give off irritating or poisonous gases.

Safety Profile

Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: hallucinations and vomiting. When heated to decomposition it emits toxic fumes of NOx,.

Potential Exposure

Used as a chemical intermediate in pharmaceuticals; as an agricultural chemical for field crops; and as a bird repellent and poison

in vitro

4-ap acts by selectively blocking fast, voltage-gated k+ channels in excitable tissues. in axons, k+ channel blockade increases the safety factor1 across demyelinated internodes and 4-ap can, therefore, restore conduction in focally demyelinated axons. 4-ap also increases calcium (ca2+) influx at presynaptic terminals thereby enabling an enhancement of neuroneuronal or neuromuscular transmission in normally myelinated neurons [1].

in vivo

investigations of the effects of 4-ap on neurologic deficits in animal in vivo models of demyelinating disease or sci have yielded inconsistent results. some trials have shown indications of potential neurological benefit, such as enhanced motor evoked potentials or reflex activity, while others have yielded no evident gains in function [1].

IC 50

170 and 230 μm at kv1.1 and kv1.2, respectively

Shipping

UN2671 Aminopyridines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials

Purification Methods

Crystallise the aminopyridine from *benzene/EtOH, then recrystallise it twice from water, then crush and dry it for 4hours at 105o [Bates & Hetzer J Res Nat Bur Stand 64A 427 1960]. It has also been crystallised from EtOH, *benzene, *benzene/pet ether, toluene and sublimes in a vacuum. [Beilstein 22/9 V 106.]

Toxicity evaluation

4-Aminopyridine is highly toxic to animals, with an approximate oral LD50 of 3.7 mg/kg body weight in the dog. 4-Aminopyridine blocks potassium channels, resulting in increased cholinergic nervous system activity. The ability of 4-aminopyridine to block potassium channels has led to some speculation that it may be an effective therapy for multiple sclerosis. Clinical signs in poisoned animals often develop within several hours of ingestion and commonly include tachycardia, salivation, tremors, ataxia, and seizures. Death from respiratory failure may develop within 4 hours of exposure. Chemical analysis of frozen stomach contents, liver, and urine is available at some diagnostic laboratories, and residues can be detected in poisoned birds. Although no specifi c antidotal therapy exists, anticonvulsants and activated charcoal administration are recommended.

Incompatibilities

Sodium nitrite, strong oxidizers. Avoid contact with acid anhydrides, acid chlorides; and strong acids.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposalIncineration with nitrogen oxides removal from effluent gas.

references

[1] hayes kc. the use of 4-aminopyridine (fampridine) in demyelinating disorders. cns drug rev. 2004 winter;10(4):295-316.

Check Digit Verification of cas no

The CAS Registry Mumber 504-24-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 4 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 504-24:
(5*5)+(4*0)+(3*4)+(2*2)+(1*4)=45
45 % 10 = 5
So 504-24-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)/p+1

504-24-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Sigma-Aldrich

  • (36687)  4-Aminopyridine  PESTANAL®, analytical standard

  • 504-24-5

  • 36687-1G

  • 255.06CNY

  • Detail
  • USP

  • (1162454)  Dalfampridine  United States Pharmacopeia (USP) Reference Standard

  • 504-24-5

  • 1162454-200MG

  • 4,647.24CNY

  • Detail
  • Aldrich

  • (275875)  4-Aminopyridine  ≥99%

  • 504-24-5

  • 275875-1G

  • 335.79CNY

  • Detail
  • Aldrich

  • (275875)  4-Aminopyridine  ≥99%

  • 504-24-5

  • 275875-5G

  • 985.14CNY

  • Detail
  • Aldrich

  • (A78403)  4-Aminopyridine  98%

  • 504-24-5

  • A78403-25G

  • 443.43CNY

  • Detail
  • Aldrich

  • (A78403)  4-Aminopyridine  98%

  • 504-24-5

  • A78403-100G

  • 1,404.00CNY

  • Detail

504-24-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-aminopyridine

1.2 Other means of identification

Product number -
Other names Dalfampridine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:504-24-5 SDS

504-24-5Synthetic route

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

N-(4-pyridyl) t-butyl carbamate

4-aminopyridine
504-24-5

4-aminopyridine

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

4-nitropyridine

4-aminopyridine
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%
4-iodopyridine
15854-87-2

4-iodopyridine

4-aminopyridine
504-24-5

4-aminopyridine

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

4-Chloropyridine

4-aminopyridine
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
isonicotinamide
1453-82-3

isonicotinamide

4-aminopyridine
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;
4-nitraminopyridine N-oxide
1124-33-0

4-nitraminopyridine N-oxide

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

N-benzyl-4-aminopyridine

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%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

4-aminopyridine
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

3,5-dibromopiperidin-4-one

4-aminopyridine
504-24-5

4-aminopyridine

Conditions
ConditionsYield
With ammonium hydroxide In dichloromethane at 40 - 45℃; for 4h;90.6%
4-aminopyridine-1-oxide
3535-75-9

4-aminopyridine-1-oxide

4-aminopyridine
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;
4-nitraminopyridine N-oxide
1124-33-0

4-nitraminopyridine N-oxide

A

4-aminopyridine
504-24-5

4-aminopyridine

B

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

4-aminopyridine-1-oxide

Conditions
ConditionsYield
With cyclohexa-1,4-diene; 5%-palladium/activated carbon In methanol at 120℃; for 0.0833333h; Microwave irradiation;A 90%
B 10%
4-azidopyridine
39910-67-3

4-azidopyridine

4-aminopyridine
504-24-5

4-aminopyridine

Conditions
ConditionsYield
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;
4-pyridylboronic acid
1692-15-5

4-pyridylboronic acid

4-aminopyridine
504-24-5

4-aminopyridine

Conditions
ConditionsYield
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%
4-pyridinecarbohydroxamic acid
4427-22-9

4-pyridinecarbohydroxamic acid

4-aminopyridine
504-24-5

4-aminopyridine

Conditions
ConditionsYield
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;
4-bromopyridine hydrochloride
19524-06-2

4-bromopyridine hydrochloride

4-aminopyridine
504-24-5

4-aminopyridine

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; lithium hexamethyldisilazane In toluene at 100℃; for 4h; Glovebox; Sealed tube;78%
4-bromopyridin
1120-87-2

4-bromopyridin

4-aminopyridine
504-24-5

4-aminopyridine

Conditions
ConditionsYield
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℃;
pyridin-4-ol
626-64-2

pyridin-4-ol

4-aminopyridine
504-24-5

4-aminopyridine

Conditions
ConditionsYield
With sodium tetrahydroborate; 5%-palladium/activated carbon; hydrazine hydrate; lithium hydroxide In 1,4-dioxane at 170℃; for 16h; Molecular sieve; Inert atmosphere;52%
4-Chloropyridine
626-61-9

4-Chloropyridine

4-aminopyridine
504-24-5

4-aminopyridine

Conditions
ConditionsYield
for 6h; Reflux; neat (no solvent);51%
2-(1,3-dithian-2-yl)propan-2-yl (pyridin-4-yl)carbamate

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

4-aminopyridine
504-24-5

4-aminopyridine

Conditions
ConditionsYield
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%
cyclohexanone-[4]pyridylhydrazone
1135-35-9

cyclohexanone-[4]pyridylhydrazone

sodium ethanolate
141-52-6

sodium ethanolate

A

4-aminopyridine
504-24-5

4-aminopyridine

B

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

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

C

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

N-ethylpyridine-4-amine

Conditions
ConditionsYield
In diethylene glycol at 235 - 240℃; for 0.25h;A 15%
B 39%
C 37%
cyclohexanone-[4]pyridylhydrazone
1135-35-9

cyclohexanone-[4]pyridylhydrazone

A

4-aminopyridine
504-24-5

4-aminopyridine

B

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

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

C

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

N-ethylpyridine-4-amine

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

(E)-4-phenylazopyridine

A

4-aminopyridine
504-24-5

4-aminopyridine

B

4-amino-phenol
123-30-8

4-amino-phenol

C

4-(2-(pyridin-4-yl)diazenyl)phenol
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

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

Conditions
ConditionsYield
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 acidA 19%
B 20%
C 22%
D 31%
N-Ethylidenasparaginsaeuredinitril

N-Ethylidenasparaginsaeuredinitril

A

4-aminopyridine
504-24-5

4-aminopyridine

B

butanedinitrile
110-61-2

butanedinitrile

C

2-Eth-(E)-ylideneamino-acrylonitrile

2-Eth-(E)-ylideneamino-acrylonitrile

D

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

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

E

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

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

Conditions
ConditionsYield
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
N-Ethylidenasparaginsaeuredinitril

N-Ethylidenasparaginsaeuredinitril

A

4-aminopyridine
504-24-5

4-aminopyridine

B

butanedinitrile
110-61-2

butanedinitrile

C

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

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

D

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

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

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

4-(N'-Pyridin-4-yl-hydrazino)-phenol

A

4-aminopyridine
504-24-5

4-aminopyridine

B

4-amino-phenol
123-30-8

4-amino-phenol

C

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

4-(2-(pyridin-4-yl)diazenyl)phenol

Conditions
ConditionsYield
With sulfuric acidA 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%
4-(4-chlorophenylazo)pyridine
20815-53-6

4-(4-chlorophenylazo)pyridine

A

4-aminopyridine
504-24-5

4-aminopyridine

B

4-(2,4-dichlorophenylazo)pyridine

4-(2,4-dichlorophenylazo)pyridine

C

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

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

D

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

4-amino-3-chlorophenol

E

2,4-Dichloroaniline
554-00-7

2,4-Dichloroaniline

F

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

(E)-4-(pyridin-4-yldiazenyl)phenol

Conditions
ConditionsYield
With sulfuric acid Rate constant; Product distribution; var. conc. of acid;A 26%
B 13%
C 15%
D 14%
E 10%
F 2%
4-(4-chlorophenylhydrazo)pyridine hydrochloride

4-(4-chlorophenylhydrazo)pyridine hydrochloride

A

4-aminopyridine
504-24-5

4-aminopyridine

B

4-(2,4-dichlorophenylazo)pyridine

4-(2,4-dichlorophenylazo)pyridine

C

2,4-Dichloroaniline
554-00-7

2,4-Dichloroaniline

D

4-chloro-aniline
106-47-8

4-chloro-aniline

E

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

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

F

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

4-(4-chlorophenylazo)pyridine

Conditions
ConditionsYield
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%
4-(2-phenylhydrazin)pyridine
72109-70-7

4-(2-phenylhydrazin)pyridine

A

4-aminopyridine
504-24-5

4-aminopyridine

B

4-amino-phenol
123-30-8

4-amino-phenol

C

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

N1-(4-pyridinyl)-1,4-benzenediamine

D

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

4-(2-(pyridin-4-yl)diazenyl)phenol

E

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

(E)-4-phenylazopyridine

F

aniline
62-53-3

aniline

Conditions
ConditionsYield
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%
4-(2-phenylhydrazin)pyridine
72109-70-7

4-(2-phenylhydrazin)pyridine

A

4-aminopyridine
504-24-5

4-aminopyridine

B

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

N1-(4-pyridinyl)-1,4-benzenediamine

C

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

(E)-4-phenylazopyridine

D

aniline
62-53-3

aniline

Conditions
ConditionsYield
With sulfuric acid Further byproducts given;A 15%
B 6%
C 9%
D 8%
4-aminopyridine
504-24-5

4-aminopyridine

2-chloroethyl isothiocyanate
1943-83-5

2-chloroethyl isothiocyanate

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

N-(2-chloroacetyl)-N'-(4-pyridyl)urea

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃;100%
In toluene at 0 - 12℃; for 12h;94%
In toluene at 20℃; for 6h;87%
4-aminopyridine
504-24-5

4-aminopyridine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

N-(4-pyridyl) t-butyl carbamate

Conditions
ConditionsYield
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%
methanesulfonic acid 3-(2-phenylethynyl-phenyl)-prop-2-ynyl ester
864950-69-6

methanesulfonic acid 3-(2-phenylethynyl-phenyl)-prop-2-ynyl ester

4-aminopyridine
504-24-5

4-aminopyridine

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

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

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;100%
4-aminopyridine
504-24-5

4-aminopyridine

2,4-dinitrophenyl benzoate
1523-15-5

2,4-dinitrophenyl benzoate

C18H14N4O6

C18H14N4O6

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 25℃; Kinetics;100%
4-aminopyridine
504-24-5

4-aminopyridine

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

2,3,4,5,6-pentachloropyridine

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

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

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 120℃; for 1h;100%
Heating;
4-aminopyridine
504-24-5

4-aminopyridine

1,12-dibromododecane
3344-70-5

1,12-dibromododecane

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

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

Conditions
ConditionsYield
In various solvent(s) for 24h; Heating;100%
4-aminopyridine
504-24-5

4-aminopyridine

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
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

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
ConditionsYield
With triethylamine In dichloromethane at 25℃; for 5h;100%
4-aminopyridine
504-24-5

4-aminopyridine

bis(4-aminopyridinium) hexafluorosilicate

bis(4-aminopyridinium) hexafluorosilicate

Conditions
ConditionsYield
With fluorosilicic acid In methanol100%
4-aminopyridine
504-24-5

4-aminopyridine

4-nitrobenzoic acid ester

4-nitrobenzoic acid ester

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

4-nitro-N-(pyridin-4-yl)benzamide

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

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
ConditionsYield
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%
4-aminopyridine
504-24-5

4-aminopyridine

2-chloroethanesulfonyl fluoride
762-70-9

2-chloroethanesulfonyl fluoride

C7H10FN2O2S(1+)*Cl(1-)

C7H10FN2O2S(1+)*Cl(1-)

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 0.0833333h; Menshutkin Reaction;100%
4-aminopyridine
504-24-5

4-aminopyridine

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

1-Bromo-2-iodobenzene

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

N-(2-bromophenyl)pyridin-4-amine

Conditions
ConditionsYield
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%
4-aminopyridine
504-24-5

4-aminopyridine

methyl iodide
74-88-4

methyl iodide

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

N-methyl-4-aminopyridinium iodide

Conditions
ConditionsYield
for 8h;99%
In ethyl acetate
In diethyl ether at 20℃;
In acetonitrile at 80℃;
4-aminopyridine
504-24-5

4-aminopyridine

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

2-(2-Dimethylamino-benzylsulfanyl)-nicotinic acid

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

2-(2-Dimethylamino-benzylsulfanyl)-N-pyridin-4-yl-nicotinamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 3h; Ambient temperature;99%
4-aminopyridine
504-24-5

4-aminopyridine

maleic anhydride
108-31-6

maleic anhydride

maleic acid 4-pyridylmonoamide

maleic acid 4-pyridylmonoamide

Conditions
ConditionsYield
In 1,4-dioxane at 20℃;99%
In tetrahydrofuran at 25℃; for 3h;78.6%
4-aminopyridine
504-24-5

4-aminopyridine

carbon monoxide
201230-82-2

carbon monoxide

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

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

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

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); trifuran-2-yl-phosphane; caesium carbonate In toluene at 90℃; under 760 Torr; for 18h; Michael addition;99%
isopropenyl (5-tert-butyl-2-(p-tolyl)-2H-pyrazol-3-yl)carbamate
865094-47-9

isopropenyl (5-tert-butyl-2-(p-tolyl)-2H-pyrazol-3-yl)carbamate

4-aminopyridine
504-24-5

4-aminopyridine

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

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

Conditions
ConditionsYield
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

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

4-aminopyridine
504-24-5

4-aminopyridine

carbon monoxide
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

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

Conditions
ConditionsYield
With trifuran-2-yl-phosphane; caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 90℃; for 18h;99%
4-aminopyridine
504-24-5

4-aminopyridine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl alcohol
75-65-0

tert-butyl alcohol

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

N-(4-pyridyl) t-butyl carbamate

Conditions
ConditionsYield
With potassium hydroxide In water99%
4-aminopyridine
504-24-5

4-aminopyridine

ammonium hexafluorophosphate

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)(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

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

Conditions
ConditionsYield
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%
4-aminopyridine
504-24-5

4-aminopyridine

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

trans-bis[O-methyl-(4-methoxyphenyl)phosphonodithioato]nickel

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

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

Conditions
ConditionsYield
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%
4-aminopyridine
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(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

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

Conditions
ConditionsYield
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%
4-aminopyridine
504-24-5

4-aminopyridine

benzyl alcohol
100-51-6

benzyl alcohol

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

N-benzyl-4-aminopyridine

Conditions
ConditionsYield
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%
4-aminopyridine
504-24-5

4-aminopyridine

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

(pyridine)2Ni{CH2CH2C(=O)O}

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

[Ni(4-aminopyridine)2(C2H4COO)]

Conditions
ConditionsYield
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%
4-aminopyridine
504-24-5

4-aminopyridine

piperonol
495-76-1

piperonol

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

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

Conditions
ConditionsYield
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%
4-aminopyridine
504-24-5

4-aminopyridine

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

pyridine-2,4-dicarboxylic acid

N-(pyridin-4-yl)isonicotinamide

N-(pyridin-4-yl)isonicotinamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;99%
4-aminopyridine
504-24-5

4-aminopyridine

ethyl bromide
74-96-4

ethyl bromide

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

4-amino-1-ethylpyridinium bromide

Conditions
ConditionsYield
In acetone for 16h; Inert atmosphere; Schlenk technique;99%
In acetone at 20℃; for 12h;95%
4-aminopyridine
504-24-5

4-aminopyridine

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

1,1,1-trifluoro-2-isocyanatoethane

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

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

Conditions
ConditionsYield
at 20℃;99%
4-aminopyridine
504-24-5

4-aminopyridine

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

3-(chlorosulfonyl)benzenesulfonyl fluoride

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

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

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction;99%
4-aminopyridine
504-24-5

4-aminopyridine

4-(chlorosulfonyl)benzenesulfonyl fluoride

4-(chlorosulfonyl)benzenesulfonyl fluoride

C11H9FN2O4S2

C11H9FN2O4S2

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

504-24-5Relevant articles and documents

Crystal Engineering in Supramolecular Polyoxometalate Hybrids through pH Controlled in Situ Ligand Hydrolysis

Roy, Soumyabrata,Mumbaraddi, Dundappa,Jain, Ankit,George, Subi J.,Peter, Sebastian C.

, p. 590 - 601 (2018)

A family of five different three-dimensional polyoxometalate (POM) based supramolecular hybrids were synthesized by a hydrothermal route under different pH using a hydrolyzable naphthalene diimide ligand. The mechanism of crystallographic phase variation of the POM-amino pyridine hybrids under different pH was studied through controlled experiments where the final hydrolyzed products were analyzed through NMR and single crystal X-ray diffraction. Different pH conditions led to variation in the extent of protonation and hydrolyzation of the ligand, yielding different phases. All of these were identified, and the structures of the supramolecular hybrids were characterized extensively. Mechanistic study proved that only the reaction conditions are responsible for the hydrolysis of the ligand and the in situ generated POM species do not have any role in it. Magnetic measurements confirmed the hexavalent oxidation states of the transition metal center (Mo) in the POM. Optical band gap measurements revealed that these hybrids are semiconducting in nature. Two of the compounds were studied for hydrogen peroxide mediated selective oxidation catalysis of small organic molecules and found to exhibit very good activity with high percentage of selectivity for the desired products of industrial importance.

Indirect reduction of CO2and recycling of polymers by manganese-catalyzed transfer hydrogenation of amides, carbamates, urea derivatives, and polyurethanes

Liu, Xin,Werner, Thomas

, p. 10590 - 10597 (2021/08/20)

The reduction of polar bonds, in particular carbonyl groups, is of fundamental importance in organic chemistry and biology. Herein, we report a manganese pincer complex as a versatile catalyst for the transfer hydrogenation of amides, carbamates, urea derivatives, and even polyurethanes leading to the corresponding alcohols, amines, and methanol as products. Since these compound classes can be prepared using CO2as a C1 building block the reported reaction represents an approach to the indirect reduction of CO2. Notably, these are the first examples on the reduction of carbamates and urea derivatives as well as on the C-N bond cleavage in amides by transfer hydrogenation. The general applicability of this methodology is highlighted by the successful reduction of 12 urea derivatives, 26 carbamates and 11 amides. The corresponding amines, alcohols and methanol were obtained in good to excellent yields up to 97%. Furthermore, polyurethanes were successfully converted which represents a viable strategy towards a circular economy. Based on control experiments and the observed intermediates a feasible mechanism is proposed.

Heterogeneous photocatalysis of azides: Extending nitrene photochemistry to longer wavelengths

Argüello, Juan E.,Lanterna, Anabel E.,Lemir, Ignacio D.,Scaiano, Juan C.

supporting information, p. 10239 - 10242 (2020/10/02)

The photodecomposition of azides to generate nitrenes usually requires wavelengths in the 300 nm region. In this study, we show that this reaction can be readily performed in the UVA region (368 nm) when catalyzed by Pd-decorated TiO2. In aqueous medium the reaction leads to amines, with water acting as the H source; however, in non-protic and non-nucleophilic media, such as acetonitrile, nitrenes recombine to yield azo compounds, while azirine-mediated trapping occurs in the presence of nucleophiles. The heterogeneous process facilitates catalyst separation while showing great chemoselectivity and high yields.

Copper(ii)-catalyzed c-n coupling of aryl halides and n-nucleophiles promoted by quebrachitol or diethylene glycol

Chen, Guoliang,Chen, Yuanguang,Du, Fangyu,Fu, Yang,Wu, Ying,Zhou, Qifan

supporting information, p. 2161 - 2168 (2019/11/25)

Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-Arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C-N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 504-24-5