| Identification | More | [Name]
2-Aminopyridine | [CAS]
504-29-0 | [Synonyms]
2-AMINOPYRIDINE
2APY
2-PYRIDINAMINE
2-PYRIDINYLAMINE
2-PYRIDYLAMINE
AKOS 91158
AKOS BBS-00004471
ALPHA-AMINOPYRIDINE
AMINOPYRIDINE, 2-
A-PYRIDYLAMINE
AURORA KA-680
PYRIDIN-2-YLAMINE
TIMTEC-BB SBB004394
1,2-dihydro-2-iminopyridine
2-aminoazabenzene
2-amino-pyridin
alpha-Pyridinamine
alpha-Pyridylamine
-Aminopyridine
aminopyridine(non-specificname) | [EINECS(EC#)]
207-988-4 | [Molecular Formula]
C5H6N2 | [MDL Number]
MFCD00006312 | [Molecular Weight]
94.11 | [MOL File]
504-29-0.mol |
| Chemical Properties | Back Directory | [Appearance]
2-Aminopyridine is a flammable, colorless crystalline solid, or white leaflets or powder, or colorless liquid with a characteristic odor | [Melting point ]
59 °C | [Boiling point ]
204-210 °C(lit.)
| [density ]
1.0308 (estimate) | [vapor pressure ]
5 hPa (125 °C) | [refractive index ]
1.5560 (estimate) | [Fp ]
198 °F
| [storage temp. ]
Store below +30°C. | [solubility ]
890g/l | [form ]
Crystalline Powder, Crystals or Flakes | [pka]
6.82(at 20℃) | [color ]
Cream to light yellow-beige | [Odor]
Characteristic odour | [Water Solubility ]
Slightly soluble. 1-5 g/100 mL at 19 ºC | [Sensitive ]
Hygroscopic | [Detection Methods]
GC,NMR | [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]
504-29-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xi | [Risk Statements ]
R21:Harmful in contact with skin.
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S38:In case of insufficient ventilation, wear suitable respiratory equipment . | [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 | [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,. | [Hazardous Substances Data]
504-29-0(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 200 mg/kg | [IDLA]
5 ppm |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Toluene-->Sodium carbonate-->Pyridine-->Sodium amide-->2-Bromopyridine-->6-Aminonicotinic acid-->Stainless steel tank | [Preparation Products]
2-Chloropyridine-->2-CHLORO-5-FLUOROISONICOTINIC ACID-->2-Bromopyridine-->2-Chloro-5-nitropyridine-->N-(3-FORMYL-2-PYRIDINYL)-2,2-DIMETHYLPROPANAMIDE-->2-Hydroxy-5-nitropyridine-->2-Fluoropyridine-5-boronic acid-->3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one-->7-CHLORO-10-(4-HYDROXYANILINO)-2-METHOXY BENZO(B)-1,5-NAPHTHY RIDINE-->2-(5-BROMO-2-PYRIDYLAZO)-5-(DIETHYLAMINO)PHENOL-->5-(AMINOMETHYL)PYRIDIN-2-AMINE-->2-Acetamido-5-fluoropyridine-->1-(2-Pyridylazo)-2-naphthol-->Lornoxicam-->2-Amino-5-nitropyridine-->2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER-->PYRIDINE-2,3,6-TRIAMINE-->2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID-->Imazosulfuron-->2-Fluoro-5-iodopyridine-->2,5-Dibromo-3-nitropyridine-->IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID-->Tenoxicam-->2-ACETAMIDO-5-AMINOPYRIDINE-->2,6-Diaminopyridine-->IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER-->Sulfasalazine-->2-Acetamido-5-nitropyridine-->2-Chloro-5-iodopyridine-->Piroxicam-->2-Benzylaminopyridine-->Sulfapyridine |
| Hazard Information | Back Directory | [General Description]
White powder or crystals or light brown solid. | [Reactivity Profile]
2-AMINOPYRIDINE(504-29-0) 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 . | [Air & Water Reactions]
Decomposes in air. Soluble in water. | [Hazard]
Toxic. | [Potential Exposure]
2-Aminopyridine is used in the manufacture of pharmaceuticals; especially antihistamines. | [Fire Hazard]
This chemical is combustible. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit | [Shipping]
UN2671 Aminopyridines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. | [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 | [Chemical Properties]
2-Aminopyridine is a flammable, colorless crystalline solid, or white leaflets or powder, or colorless liquid with a characteristic odor | [Waste Disposal]
Incineration with nitrogen oxides removal from effluent gas. | [Physical properties]
Colorless to yellow crystals, leaflets, flakes, or powder with a characteristic odor. May darken
after prolonged storage. | [Uses]
Compound 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.
2-Aminopyridine is used primarily in the pharmaceutical industry as an intermediate in chemical synthesis.
2-Aminopyridine is a basic building block of several heterocyclic compounds and Schiff bases.
2-Aminopyridine (2AP) 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. | [Uses]
The main use of 2-aminopyridine is in manufacturing pharmaceuticals
such as antihistamines. | [Uses]
Used to label neutral and acidic glycans for fluorescent and UV detection in HPLC.1
2-AP has also been used to derivatize sialyloligosaccharides for detection in FAB-MS.2
2-Aminopyridine has been used as a reactant in the synthesis of 2-(2-aminopyridinium)acetyl starch with antioxidant property.
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. | [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. | [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). | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 72, p. 4554, 2007 DOI: 10.1021/jo070189y
Tetrahedron Letters, 11, p. 3901, 1970 | [Health Hazard]
2-Aminopyridine causes central
nervous system effects. | [Flammability and Explosibility]
Notclassified | [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). | [Purification Methods]
It crystallises from *benzene/pet ether (b 40-60o) or CHCl3 /pet ether. [Beilstein 22/8 V 280.] | [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. |
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