2-アミノピリジン 化学特性,用途語,生産方法
外観
白色～ほとんど白色, 結晶～結晶性粉末
溶解性
有機溶媒に可溶。
用途
糖鎖還元末端の蛍光ラベル化剤。
用途
スルファジンなどの医薬品原料。ビスマス、アンチモン、金の検出に用いる。
化学的特性
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.
使用
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.
主な応用
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.
製造方法
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).
一般的な説明
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)
空気と水の反応
Decomposes in air. Soluble in water.
反応プロフィール
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 .
危険性
Toxic.
健康ハザード
2-Aminopyridine causes central
nervous system effects.
火災危険
2-Aminopyridine is combustible.
安全性プロファイル
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,.
職業ばく露
2-Aminopyridine is used in the manufacture of pharmaceuticals; especially antihistamines.
発がん性
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.
環境運命予測
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).
輸送方法
UN2671 Aminopyridines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
純化方法
It crystallises from *benzene/pet ether (b 40-60o) or CHCl3 /pet ether. [Beilstein 22/8 V 280.]
不和合性
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
廃棄物の処理
Incineration with nitrogen oxides removal from effluent gas.
参考文献
[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-アミノピリジン 上流と下流の製品情報
原材料
準備製品
スルファサラジン
2,6-ジアミノピリジン
2-アセトアミド-5-フルオロピリジン
PAN
3-(2-クロロエチル)-6,7,8,9-テトラヒドロ-2-メチル-4H-ピリド[1,2-a]ピリミジン-4-オン
ピロキシカム
2,5-ジブロモ-3-ニトロピリジン
テノキシカム
2-ベンジルアミノピリジン
2-フルオロピリジン-5-ボロン酸
2-アセトアミド-5-アミノピリジン
2-メチルイミダゾ[1,2-a]ピリジン-3-カルボン酸
2-(5-ブロモ-2-ピリジルアゾ)-5-(ジエチルアミノ)フェノール
2-ブロモピリジン
N-(3-ホルミル-2-ピリジニル)-2,2-ジメチルプロパンアミド
2-アミノ-5-ニトロピリジン
2-アセトアミド-2-ニトロピリジン
7-CHLORO-10-(4-HYDROXYANILINO)-2-METHOXY BENZO(B)-1,5-NAPHTHY RIDINE
イマゾスルフロン
ロルノキシカム
イミダゾ[1,2-A]ピリジン-2-カルボン酸ナトリウム0.5水和物
5-(AMINOMETHYL)PYRIDIN-2-AMINE
2-メチル-イミダゾ[1,2-A]ピリジン-3-カルボン酸エチルエステル
2-フルオロ-5-ヨードピリジン
2-ヒドロキシ-5-ニトロピリジン
スルファピリジン
2-クロロ-5-ニトロピリジン
ピリジン-2,3,6-トリアミン
2-CHLORO-5-FLUOROISONICOTINIC ACID
イミダゾ[1,2-A]ピリジン-2-カルボン酸エチルエステル
2-クロロ-5-ヨードピリジン 塩化物 ヨウ化物
2-クロロピリジン