2-Amino-4-bromopyridine
2-amino-4-bromopyridine
CAS: 84249-14-9
Molecular Formula: C5H5BrN2
2-Amino-4-bromopyridine - Names and Identifiers
| Name | 2-amino-4-bromopyridine |
| Synonyms | AURORA 23224 AKOS BBS-00001381 OTAVA-BB BB7110952492 4-BROMOPYRIDIN-2-AMINE 4-Bromo-2-pyridinamine 2-Amino-4-bromopyridine 4-Bromo-2-amine-pyridin 2-AMINO-4-BROMOPYRIDINE 4-Bromo-2-aminopyridine 2-amino-4-bromopyridine 4-Bromopyridine-2-amine 2-Amino-4-bromo pyridine 4-BROMO-PYRIDIN-2-YLAMINE 2--4- aMinopyridinebroMide |
| CAS | 84249-14-9 |
| EINECS | 640-931-5 |
| InChI | InChI:1S/C5H5BrN2/c6-4-1-2-8-5(7)3-4/h1-3H,(H2,7,8) |
| InChIKey | BAQKUNMKVAPWGU-UHFFFAOYSA-N |
2-Amino-4-bromopyridine - Physico-chemical Properties
| Molecular Formula | C5H5BrN2 |
| Molar Mass | 173.01 |
| Density | 1.710±0.06 g/cm3(Predicted) |
| Melting Point | 142-146 °C |
| Boling Point | 268.2±20.0 °C(Predicted) |
| Flash Point | 116 °C |
| Solubility | Chloroform (Slightly), Methanol (Slightly) |
| Appearance | White crystal |
| Color | Off-White to Beige |
| pKa | 5.72±0.11(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| MDL | MFCD01646115 |
2-Amino-4-bromopyridine - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R36 - Irritating to the eyes R22 - Harmful if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| HS Code | 29333990 |
| Hazard Class | IRRITANT |
2-Amino-4-bromopyridine - Reference Information
| Overview | 2-amino-4-bromopyridine, also known as 4-bromo-2-aminopyridine, because the bromine atom and amino group in the molecule can continue to biochemically introduce other functional groups, many novel and diverse heterocyclic compounds can be designed and synthesized, therefore, 2-Amino-4-bromopyridine is a widely used pharmaceutical intermediate. |
| Use | 2-amino-4-bromopyridine is a compound that can be used in organic synthesis. |
| preparation | CN201510652275.8 provides a new synthesis method of 2-amino -4 bromopyridine. the method has low raw material cost, high yield, simple reaction operation, convenient treatment of three wastes and easy industrialization. Including the following steps:(1) esterification reaction: 4-bromopyridine hydrochloride esterification to obtain 4-bromopyridine-2-ethyl formate crude product;(2) Ammoniation reaction: 4-bromopyridine-2-ethyl formate crude product is ammoniated to obtain 4-bromopyridine-2-formamide;(3) Hoffmann degradation reaction: 4-bromopyridine-2-formamide is degraded by Hoffman to obtain 2-amino-4-bromopyridine; Step 1: add ethyl pyruvate to a 20-liter three-mouth bottle, cool the temperature to 0 degrees, add hydrogen peroxide dropwise under mechanical stirring, control the temperature below 0 degrees during the dropwise process, and place it for use after the dropwise; add dichloromethane and 4-bromopyridine hydrochloride free dichloromethane solution in a 200-liter reactor (for example, take 5kg of 4-bromopyridine hydrochloride, dissolve it in 30 liters of water, and adjust the PH to 8 with sodium bicarbonate, use 50 liters of dichloromethane to extract three times), ferrous sulfate and a sulfuric acid aqueous solution with a concentration of 50wt%, stir and cool down to minus 10 degrees, drop the reagent prepared in a 20-liter reaction bottle before dropping, the drop process temperature is controlled between minus 10 degrees and 0 degrees, after dropping, heat preservation and stirring for one hour, TCL detection reaction is finished, the reaction system is added to 100 liters of water, fully stirred for 30 minutes, and the liquid is separated, repeat this operation until the water phase is colorless and the organic phase is concentrated to obtain 8.5kg of crude product, which is brown-red liquid A. It does not need purification and is directly used in the next step. Step 2: Add 8.5kg of A into 35 liters of ammonia water in batches, stir methane overnight, centrifuge to obtain crude product, soak with ethyl acetate, centrifuge to obtain 4.5kg of amide; Step 3: Add water and sodium hydroxide to a 50-liter reaction kettle, cool down to 0 degrees under stirring, add bromine dropwise, cool down to minus 10 degrees after dropping, add amide in batches, add heat preservation and stir for one hour, then heat to 80 degrees for one hour, TCL detected the end of the reaction, dropped to room temperature, centrifuged to obtain crude product, crystallized with toluene to obtain 1.5kg of pure product. |
Last Update：2024-04-09 15:16:35
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