2-pyridiylamine
2-Aminopyrimidine
CAS: 109-12-6
Molecular Formula: C4H5N3
2-pyridiylamine - Names and Identifiers
| Name | 2-Aminopyrimidine |
| Synonyms | 2-pyridiylamine 2-Aminopyrimide 2-Pyrimidinamine 2-Pyrimidinemine PYRIMIDIN-2-AMINE 2-Aminopyrimidine pyrimidin-2-amine 2-amino-pyrimidin PYRIMIDIN-2-YLAMINE TIMTEC-BB SBB004387 2-Amino-1,3-diazine Aminopyrimidine, 2- pyrimidin-2-ylamine pyrimidin-2-amine analogue 1,2-dihydro-2-imine-pyrimidin |
| CAS | 109-12-6 |
| EINECS | 203-648-4 |
| InChI | InChI=1/C4H5N3/c5-4-6-2-1-3-7-4/h1-3H,(H2,5,6,7) |
| InChIKey | LJXQPZWIHJMPQQ-UHFFFAOYSA-N |
2-pyridiylamine - Physico-chemical Properties
| Molecular Formula | C4H5N3 |
| Molar Mass | 95.1 |
| Density | 1.1031 (rough estimate) |
| Melting Point | 122-126 °C (lit.) |
| Boling Point | 158 °C (139.5186 mmHg) |
| Flash Point | 103 °C |
| Water Solubility | SOLUBLE |
| Solubility | Easily soluble in water, alcohol, acetone and chloroform, slightly soluble in ether and benzene. Easy to sublimate. |
| Vapor Presure | 0.00521mmHg at 25°C |
| Appearance | Colorless crystal |
| Color | White to light yellow |
| BRN | 107014 |
| pKa | 3.45(at 20℃) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.5200 (estimate) |
| MDL | MFCD00006089 |
| Physical and Chemical Properties | Melting point 124-127°C boiling point 158 ° C (186 mmHg) flash point 103°C water-SOLUBLE solution |
| Use | Used as a pharmaceutical Intermediate |
2-pyridiylamine - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| UN IDs | UN 2811 |
| WGK Germany | 3 |
| RTECS | UV6326000 |
| FLUKA BRAND F CODES | 8 |
| TSCA | Yes |
| HS Code | 29335995 |
2-pyridiylamine - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Uses | Used in organic synthesis, as pharmaceutical intermediates and biochemical reagents. Used as a pharmaceutical intermediate |
| Production method | Using furochloric acid and guanidine nitrate as raw materials, it is obtained by cyclization, decarboxylation and dechlorination. The methanol solution of sodium methoxide and guanidine nitrate were added and filtered within 30min at 40-45 ℃ to obtain the methanol solution of free guanidine. This solution is added into a reaction tank, furfuric acid-methanol solution is added within 95 ℃ for 30min, after addition, heat preservation at 60±1 ℃ for 40min, decompression distillation is carried out, methanol is distilled to a certain amount, distillation is stopped, reactants are dissolved in water, acidified with 30% hydrochloric acid to pH = 1 at 30-35 ℃, filtered and washed with water, and dried at 95 ℃ to obtain crude cyclists. The crude cyclidine is placed in a sublimator, and decarboxylated and sublimated at 150-300 ℃ to obtain 2-amino -5-chloridine [5428-89-7]. The yield of cyclization and decarboxylation is about 67.5%. Isopropanol, water caustic soda, zinc mud, (zinc hydroxide 60%), 2-amino -5-chloropyrimidine and zinc powder are added to the reaction tank. After reflux at 77-80 ℃ for 8 hours, low boiling point distillate is recovered first, and isopropanol is recovered at 77-100 ℃. Cold to 77-85 ℃ and filter, wash the filter cake with hot water. The filtrate and part of the lotion are combined, granular caustic soda is added, and alkali is analyzed below 50 ℃ for 1h. Extract with formaldehyde ester below 70 ℃, separate the jelly, adjust the pH = 7.5-8 with hydrochloric acid, then separate the oil, and then recover the formaldehyde ester to precipitate 2-aminopyrimidine. The finished product was dried at 40-50 ℃ with a yield of 85.7%. Another method is to react with guanidine hydrochloride and propargaldehyde. Add 90ml concentrated hydrochloric acid to a 300ml three-mouth flask equipped with a thermometer, a dropping funnel and a stirrer, and cool the outside with an ice salt bath. Under stirring condition, 27g of guanidine hydrochloride with a purity of about 80% is added below 10 ℃. After the carbon dioxide is released, it is cooled to 0 ℃, and 11.1g of crude propargaldehyde (8.7g of pure product) is dripped. When dripping, the reaction temperature will rise accordingly, but the control shall not exceed 20 ℃. After the exotherm of the reaction is stopped, it is placed overnight at room temperature, then the reaction liquid is moved into a distillation flask, evaporated and concentrated under reduced pressure at about 35°C, and after cooling, 60ml of 30% sodium hydroxide solution is added to precipitate the product 2-aminopyrimidine. The substance is extracted with 1500ml benzene at 60-70 ℃, and the benzene solution is cooled and dried with calcium chloride. Distillation removes benzene to obtain 10.2-10.7g of product with a yield of 66.5%-70%. Melting point 125-127 ℃. |
Last Update：2024-04-09 21:11:58
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