ChemicalBook > CAS DataBase List > 2-Aminopyridine

2-Aminopyridine

Product Name
2-Aminopyridine
CAS No.
504-29-0
Chemical Name
2-Aminopyridine
Synonyms
PYRIDIN-2-YLAMINE;2-PYRIDINAMINE;2-amino-pyridin;2-PYRIDYLAMINE;2APY;NSC 431;AKOS 91158;AURORA KA-680;2-Pyridylamin;A-PYRIDYLAMINE
CBNumber
CB8152736
Molecular Formula
C5H6N2
Formula Weight
94.11
MOL File
504-29-0.mol
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2-Aminopyridine Property

Melting point:
59 °C
Boiling point:
204-210 °C(lit.)
Density 
1.0308 (estimate)
bulk density
600kg/m3
vapor pressure 
5 hPa (125 °C)
refractive index 
1.5560 (estimate)
Flash point:
198 °F
storage temp. 
Store below +30°C.
solubility 
890g/l
pka
6.82(at 20℃)
form 
Crystalline Powder, Crystals or Flakes
color 
Cream to light yellow-beige
Odor
Characteristic odour
Water Solubility 
Slightly soluble. 1-5 g/100 mL at 19 ºC
Sensitive 
Hygroscopic
Merck 
14,473
BRN 
105785
Exposure limits
NIOSH REL: TWA 0.5 ppm (2 mg/m3), IDLH 5 ppm; OSHA PEL: 0.5 ppm; ACGIH TLV: TWA 0.5 ppm.
LogP
0.53
CAS DataBase Reference
504-29-0(CAS DataBase Reference)
NIST Chemistry Reference
2-Pyridinamine(504-29-0)
EPA Substance Registry System
2-Aminopyridine (504-29-0)
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Safety

Hazard Codes 
T,Xi
Risk Statements 
21-25-36/37/38-23/24/25
Safety Statements 
26-36/37/39-45-38-28B
OEB
B
OEL
TWA: 0.5 ppm (2 mg/m3)
RIDADR 
UN 2671 6.1/PG 2
WGK Germany 
3
RTECS 
US1575000
F 
8-21
Autoignition Temperature
>630 °C
Hazard Note 
Toxic/Irritant
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29333999
Hazardous Substances Data
504-29-0(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 200 mg/kg
IDLA
5 ppm
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.01113
Product name
2-Aminopyridine
Purity
for synthesis
Packaging
100g
Price
$82.2
Updated
2024/03/01
Sigma-Aldrich
Product number
8.01113
Product name
2-Aminopyridine
Purity
for synthesis
Packaging
500g
Price
$312
Updated
2024/03/01
Sigma-Aldrich
Product number
09340
Product name
2-Aminopyridine
Purity
purum, ≥98.0% (NT)
Packaging
50g
Price
$33.7
Updated
2024/03/01
Sigma-Aldrich
Product number
09340
Product name
2-Aminopyridine
Purity
purum, ≥98.0% (NT)
Packaging
250g
Price
$74.1
Updated
2024/03/01
TCI Chemical
Product number
A0411
Product name
2-Aminopyridine
Purity
>99.0%(GC)(T)
Packaging
25g
Price
$18
Updated
2024/03/01
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2-Aminopyridine Chemical Properties,Usage,Production

Chemical Properties

2-Aminopyridine is a yellow or white crystalline (sand-like) solid with a characteristic odor. It is soluble in water, alcohol, benzene, ether and hot petroleum ether. It tastes bitter and has anesthetic effect. It is a significant synthetic synthon, with unique dual nucleophilic structure. It can react with ketones, aldehydes, acids, multifunctional esters, halogenated aromatics and other compounds to synthesize five- and six-member azaheterocycles. after prolonged storage, may darken in color.

Uses

2-Aminopyridine is used primarily in the pharmaceutical industry as an intermediate in chemical synthesis. It is used to manufacturing analgesic and anti-inflammatory drugs piroxicam and lornoxicam. 2-Aminopyridine is a basic building block of several heterocyclic compounds and Schiff bases. It has been shown to reversibly block voltage-dependent potassium channels, and is also a common impurity from the synthesis of compounds found in hair dyes. It is a derivatizing agent which can be used as a fluorescent label for oligosaccharide detection, chromatographic separation, fluorometric or mass spectrometric analysis. 2AP and its derivatives are good candidates for antimicrobial, anticorrosion and molecular sensing applications.

Preparation

2-Aminopyridine is manufactured using the reaction of pyridine with sodium amide (Chichibabin amination). It is obtained in high yield after the hydrolysis of the intermediate salt (Merck, 2001; Shimizu et al., 1993).

Application

2-Aminopyridine has also been used to derivatize sialyloligosaccharides for detection in FAB-MS. It can also be used:
As a reactant in the synthesis of 3-aroylimidazopyridines from chalcones by aerobic oxidative amidation using copper acetate catalyst.
In the synthesis of crystalline Cu(II) complex, di-μ-(2-aminopyridine(N,N′))-bis[(2,6 pyridinedicarboxylate)aquacopper(II)] tetrahydrate using 2,6-pyridinedicarboxylic acid and Cu(CH3COO)2.H2O.
As an imprinting molecule for the preparation of poly(methacrylic acid–ethylene glycol dimethacrylate) polymer. It is packed in micro-column for selective solid phase extraction of 2-aminopyridine.
As a reactant in the synthesis of 2-aryl-3-(pyridin-2-yl)-1,3-thiazolidin-4-ones in the presence of Lewis acid catalysts.
As a reactant in the synthesis of 2-(2-aminopyridinium)acetyl starch with antioxidant property.

Synthesis Reference(s)

The Journal of Organic Chemistry, 72, p. 4554, 2007 DOI: 10.1021/jo070189y
Tetrahedron Letters, 11, p. 3901, 1970

General Description

2-aminopyridine appears as white powder or crystals or light brown solid. It is soluble in water and alcohol. It is toxic by ingestion and by inhalation of the dust. It is used to make pharmaceuticals and dyes. (NTP, 1992)

Air & Water Reactions

Decomposes in air. Soluble in water.

Reactivity Profile

2-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. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. Reacts with oxidizing agents .

Hazard

Toxic.

Health Hazard

2-Aminopyridine causes central nervous system effects.

Fire Hazard

2-Aminopyridine is combustible.

Biological Activity

Aminopyridine 2 (1-((6-aminopyridin-3-yl)methyl)-3-(4-bromophenyl)urea) is an orally available, potent and selective irreversible inhibitor of myeloperoxidase (MPO) th at blocks vasomotor dysfunction in r at aortic rings. Aminopyridine 2 inhibits myeloperoxidase in a mouse model of peritonitis.

Safety Profile

Poison by ingestion, inhalation, subcutaneous, intravenous, and intraperitoneal routes. Toxic effects resemble strychnine poisoning. Human systemic effects by inhalation: somnolence, convulsions, and antipsychotic effects. Human central nervous system effects by inhalation. When heated to decomposition it emits highly toxic fumes of NOx,.

Potential Exposure

2-Aminopyridine is used in the manufacture of pharmaceuticals; especially antihistamines.

Carcinogenicity

The LD50 in mice by intraperitoneal injection was 35 mg/kg; lethal doses in animals also produced excitement, tremors, convulsions and tetany.1 Fatal doses were readily absorbed through the skin. A 0.2 M aqueous solution dropped in a rabbit’s eye was only mildly irritating.
2-Aminopyridine was not mutagenic in a variety of Salmonella tester strains with or without metabolic activation.

Environmental Fate

Soil. When radio-labeled 4-aminopyridine was incubated in moist soils (50%) under aerobic conditions at 30 °C, the amount of 14CO2 released from an acidic loam (pH 4.1) and an alkaline, loamy sand (pH 7.8) was 0.4 and 50%, respectively (Starr and Cunningham, 1975).
Chemical/Physical. Releases toxic nitrogen oxides when heated to decomposition (Sax and Lewis, 1987).

Shipping

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

Purification Methods

It crystallises from *benzene/pet ether (b 40-60o) or CHCl3 /pet ether. [Beilstein 22/8 V 280.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides

Waste Disposal

Incineration with nitrogen oxides removal from effluent gas.

References

[1] RAO R N, CHANDA K. 2-Aminopyridine – an unsung hero in drug discovery[J]. Chemical Communications, 2021, 3: 343-382. DOI:10.1039/D1CC04602K.
[2] D. M. BYSTROV  L. L F. Reactivity of 2-aminopyridine N-oxides[J]. Russian Chemical Bulletin, 2024, 73 1: 33-52. DOI:10.1007/s11172-024-4120-2.
[3] KUMPINA I, BASKEVICS V, WALBY G D, et al. Synthesis of 2-Aminopyridine-Modified Peptide Nucleic Acids[J]. Synlett, 2023, 25 1: 0. DOI:10.1055/a-2191-5774.
[4] MEHMET TüMER. Antimicrobial activity studies of the binuclear metal complexes derived from tridentate Schiff base ligands[J]. Transition Metal Chemistry, 1999, 24 4: 414-420. DOI:10.1023/A:1006973823926.

2-Aminopyridine Preparation Products And Raw materials

Raw materials

2-Bromopyridine Toluene Stainless steel tank Pyridine Sodium amide 6-Aminonicotinic acid Sodium carbonate

Preparation Products

Sulfasalazine 2,6-Diaminopyridine 2-Acetamido-5-fluoropyridine 1-(2-Pyridylazo)-2-naphthol 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Piroxicam 2,5-Dibromo-3-nitropyridine Tenoxicam 2-Benzylaminopyridine 2-Fluoropyridine-5-boronic acid 2-ACETAMIDO-5-AMINOPYRIDINE 2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID 2-(5-BROMO-2-PYRIDYLAZO)-5-(DIETHYLAMINO)PHENOL 2-Bromopyridine N-(3-FORMYL-2-PYRIDINYL)-2,2-DIMETHYLPROPANAMIDE 2-Amino-5-nitropyridine 2-Acetamido-5-nitropyridine 7-CHLORO-10-(4-HYDROXYANILINO)-2-METHOXY BENZO(B)-1,5-NAPHTHY RIDINE Imazosulfuron Lornoxicam IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 5-(AMINOMETHYL)PYRIDIN-2-AMINE 2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER 2-Fluoro-5-iodopyridine 2-Hydroxy-5-nitropyridine Sulfapyridine 2-Chloro-5-nitropyridine PYRIDINE-2,3,6-TRIAMINE 2-CHLORO-5-FLUOROISONICOTINIC ACID IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER 2-Chloro-5-iodopyridine 2-Chloropyridine
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View Lastest Price from 2-Aminopyridine manufacturers

Hebei Mujin Biotechnology Co.,Ltd
Product
2-Aminopyridine 504-29-0
Price
US $0.00/Kg/Bag
Min. Order
1ASSAYS
Purity
99%
Supply Ability
20ton
Release date
2021-10-09
Shanghai UCHEM Inc.
Product
2-aminopyridine 504-29-0
Price
US $59.00/kg
Min. Order
1kg
Purity
0.98
Supply Ability
25kg
Release date
2023-11-13
Shaanxi Dideu Medichem Co. Ltd
Product
2-Aminopyridine 504-29-0
Price
US $0.00-0.00/KG
Min. Order
1g
Purity
99%
Supply Ability
2000tons
Release date
2019-12-31

504-29-0, 2-AminopyridineRelated Search:

2-Chloro-3-cyanopyridine EC 2.6.1.2 ALTRENOGEST Pyridine Acetaminophen Tris(hydroxymethyl)aminomethane 6-Aminocaproic acid (2-AMINO-PYRIDIN-4-YL)-METHANOL Glycine Diethylstilbestrol 2-Hydrazinopyridine 4-(2-PYRIDYLAZO)RESORCINOL 2-Anilinopyridine 2-(2-AMINOETHYLAMINO)-5-NITROPYRIDINE 4-Dimethylaminopyridine 3-Aminopyridine 3-ETHOXY-2-NITROPYRIDINE 2-(Methylamino)pyridine

  • PYRIDIN-2-YLAMINE
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  • 2-AMINO PYRIDINE PYRIDIN-2-YLAMINE
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  • a-Aminopyridine
  • 2-Aminopyridine,2-AP, 2-Pyridinamine, 2-Pyridylamine
  • 2(1H)-Pyridinimine
  • AMINOPYRIDINE, 2-(RG)
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  • 2-Aminopyridine chemical book
  • Mepyramine maleate EP Impurity C
  • Piroxicam EP Impurity A
  • Piroxicam Impurity 1(Piroxicam EP Impurity A)
  • Tenoxicam Impurity 1(EP Impurity A)
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  • Tenoxicam EP Impurity A
  • Mepyramine EP Impurity C (Tenoxicam EP Impurity A/ Piroxicam EP Impurity A/ 2-Aminopyridine)
  • Piroxicam EP Impurity A (Tenoxicam EP Impurity A/ Mepyramine EP Impurity C/ 2-Aminopyridine)