Name | 2-Aminopyridine |
Synonyms | 2APY AURORA KA-680 2-pyridylamine 2-Pyridinamine A-PYRIDYLAMINE 2-amino-pyridin 2-Aminopyridine 2-Amino Pyridine Aminopyridine, 2- 2-aminopyridinium PYRIDIN-2-YLAMINE 2-aminoazabenzene alpha-Pyridinamine TIMTEC-BB SBB004394 1,2-dihydro-2-iminopyridine |
CAS | 504-29-0 |
EINECS | 207-988-4 |
InChI | InChI=1/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7)/p+1 |
Molecular Formula | C5H6N2 |
Molar Mass | 94.11 |
Density | 1.0308 (estimate) |
Melting Point | 59 °C |
Boling Point | 204-210°C(lit.) |
Flash Point | 198°F |
Water Solubility | Slightly soluble. 1-5 g/100 mL at 19 ºC |
Solubility | 890g/l |
Vapor Presure | 5 hPa (125 °C) |
Appearance | Crystalline Powder, Crystals or Flakes |
Color | Cream to light yellow-beige |
Odor | Characteristic odour |
Exposure Limit | NIOSH REL: TWA 0.5 ppm (2 mg/m3), IDLH 5 ppm; OSHA PEL: 0.5 ppm;ACGIH TLV: TWA 0.5 ppm. |
Merck | 14,473 |
BRN | 105785 |
pKa | 6.82(at 20℃) |
Storage Condition | Store below +30°C. |
Sensitive | Hygroscopic |
Refractive Index | 1.5560 (estimate) |
Physical and Chemical Properties | appearance crystalline, toxic. Irritant, organic synthesis. Drug
|
Use | Raw materials for the manufacture of drugs, detergents, fungicides |
Risk Codes | 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 Description | 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 the label whenever possible.) S38 - In case of insufficient ventilation, wear suitable respiratory equipment. S28B - |
UN IDs | UN 2671 6.1/PG 2 |
WGK Germany | 3 |
RTECS | US1575000 |
FLUKA BRAND F CODES | 8-21 |
TSCA | Yes |
HS Code | 29333999 |
Hazard Note | Toxic/Irritant |
Hazard Class | 6.1 |
Packing Group | II |
Toxicity | LD50 orally in Rabbit: 200 mg/kg |
Raw Materials | Sodium amide Pyridine Toluene |
Downstream Products | 2-Bromopyridine Salazosulfapyridine piroxicam usp |
LogP | 0.53 |
NIST chemical information | information provided by: webbook.nist.gov (external link) |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
Introduction | 2-aminopyridine, English name 2-aminopyridine, is a white flake or crystalline solid, the melting point was 57-58 °c. 2-aminopyridine is widely used in the production of chemical products, for example, it can be converted into azo compounds by diazotization reaction of 2-amino group, and azo compounds are an important class of synthetic dye intermediates. |
Application | in the field of medicine, 2-aminopyridine, as an important pharmaceutical intermediate, can be condensed, hydrolysis of the sulfonamide antibacterial drug-pyridine sulfonamide. Sulfasalazine was prepared by coupling and acidification of sulfasalazine after diazotization with salicylic acid. Sulfasalazine is a sulfa drug which is not easily absorbed orally. It is hydrolyzed into 5-aminosalicylic acid and sulfapyridine through intestinal microbial absorption. In addition, 2-aminopyridine is also used in the synthesis of analgesic anti-inflammatory drugs-piroxicam, Lornoxicam, etc., for osteoarthritis, rheumatoid arthritis and ankylosing spondylitis symptom relief. |
preparation | a method for preparing 2-aminopyridine by using 2-OP distillation residue, comprising the following steps: 2-OP distillation residue in situ-catalytic cracking and vacuum distillation: the zeolite or silica gel is impregnated with a 10% ~ 80% mass% Phosphoric acid aqueous solution for 2~48 hours and then filtered to remove the liquid phase, the solid material obtained is burned in a muffle furnace at 300 ° C. To 800 ° C. For 2 to 12 hours, and then the solid material after being burned at high temperature is pulverized to obtain phosphorylated zeolite or phosphorylated silica gel; the phosphorylated zeolite and/or phosphorylated silica gel and 2-OP distillation residue are added into the pyrolysis reactor according to the mass ratio of 1~10: 10~1000, and under the conditions of stirring, temperature of 240 ℃ ~ 400 ℃ and vacuum degree of 0.01MPa ~ 0.1MPa, that is, a vacuum distillation distillate containing pyridine-2-carboxamide was obtained in a yield of 60% to 90% relative to the mass of the 2-OP distillation residue. The distillate is cooled and crystallized to obtain a crude pyridine-2-carboxamide. Add crude pyridine-2-carboxamide (2g) and 10% aqueous sodium hydroxide solution (20 ml) to a suitable round bottom flask, the NaClO solution (active chlorine content about 5%,20 ml) was slowly added dropwise after the ice bath was cooled to 0-5 °c. After completion of the dropwise addition, the reaction mixture was warmed to 75-80 °c and reacted for about 1.5 hours until the starting material content was less than 1% as monitored by HPLC. After completion of the reaction, the reaction solution was cooled to room temperature, and extracted three times with dichloromethane (20 ml). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product was recrystallized from toluene and dried to give a white solid in 75% yield. Add the crude pyridine-2-carboxamide prepared above (2g) and 10% aqueous sodium hydroxide solution (20 ml) to a suitable round bottom flask, the NaBrO solution (20 ml, prepared by mixing liquid bromine with sodium hydroxide solution) was slowly added dropwise after cooling to 0-5 °c in an ice bath. After completion of the dropwise addition, the reaction mixture was warmed to 75-80 °c and reacted for about 1.5 hours until the starting material content was less than 1% as monitored by HPLC. After completion of the reaction, the reaction solution was cooled to room temperature, and extracted three times with dichloromethane (20 ml). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product was recrystallized from toluene and dried to give a white solid in 78% yield. |
uses | for organic synthesis, can be used as intermediates and chemical reagents for drugs and dyes. used as an intermediate in organic synthesis used as an analytical reagent, and also used in microscopic microcrystalline analysis and organic synthesis used as a raw material in the manufacture of drugs, detergents and fungicides organic synthesis, intermediates, chemical reagents for drugs and dyes. Organic synthesis intermediates were used as analytical reagents, microcrystallite analysis and organic synthesis were used to examine antimony, bismuth, cobalt, copper, gold and zinc antimony, bismuth, cobalt, copper, gold and zinc. Organic Synthesis. Used as an intermediate in the manufacture of pharmaceuticals, and also used in organic synthesis |
production method | the reaction of sodium amino acid with pyridine is usually carried out in the presence of a solvent. During the reaction, hydrogen gas is evolved and a sodium derivative of aminopyridine is produced, which is hydrolyzed to produce free aminopyridine. Operation example 1 sodium amino acid was added to dry toluene, heated to reflux, pyridine was added and nitrogen gas was passed through, and reflux was continued for 6 hours. At the end of the reaction, the reaction was cooled to 20 ℃, nitrogen was permeated, water was slowly added, and the temperature was increased to 60-70 ℃. The toluene layer was separated by standing, the water layer was maintained at 60-70 ℃, and extracted twice with toluene, the toluene was recovered under reduced pressure, and the distillate was collected at 100-140 ° C. (8kPa) to obtain 2-aminopyridine. The yield was 66-70%. Operating example 2 toluene was added to a dry stainless steel tank, heated, and the toluene was distilled off until the distillate was clear. After cooling to below 35 °c, sodium amino acid was added. The temperature was raised to 108 °c, and pyridine was added dropwise. After addition, reflux was performed for 6H. Cooled to 40 °c water was added and stirred at 70 °c for 1H. Cold to below 30 ℃, The aqueous layer was separated (extracted once with toluene). The toluene layer was dried with anhydrous sodium carbonate. After the toluene was recovered, it was cooled and solidified to give 2-aminopyridine. The yield was 65%. The other 6-aminonicotinic acids of 2-aminopyridine are decarboxylated by melting at a temperature above the melting point; Are prepared from pyridinecarboxamide by the Hoffmann reaction; By aminolysis of 2-bromopyridine. In industrial production, the newly prepared sodium amino acid particles and toluene are added to the reactor, and when heated to 110 ° C with slight reflux, pyridine is added dropwise under stirring, and the reaction rate is controlled by cooling. After the reaction is slow, continue heating, stirring and refluxing for 3H; Cool to 40 ℃ and add water to decompose. When all the reactants are dissolved, separate the lower alkali solution while it is hot, distill off the toluene in the oil layer, distill it under reduced pressure, and solidify after cooling, white crystals were obtained with a yield of 60%-63%. |
category | toxic substances |
toxicity grade | high toxicity |
Acute toxicity | oral-rat LD50: 200 mg/kg; Oral-mouse LD50: 145 mg/kg |
flammability hazard characteristics | open flame flammable; High thermal decomposition of toxic nitrogen oxide gases |
storage and transportation characteristics | The warehouse is ventilated and dried at low temperature, separate storage of food additives |
extinguishing agent | dry powder, foam, carbon dioxide, sand, anti-soluble foam. |
Occupational Standards | TLV-TWA 0.5 PPM (2 mg/m3); PEL 1.5 PPM (6 mg/m3) |
spontaneous combustion temperature | >630°C |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
immediate life-and health-threatening concentration | 5 ppm |