Name | 4-Aminopyridine |
Synonyms | Fampridine phillips1861 Phillips 1861 4-pyridylamine pyridin-2-amine 4-Aminopyridine Amino-4-pyridine 4-aminopyridinium PARA-AMINOPYRIDINE Pimadin (free base) gamma-aminopyridine AMINOPYRIDINE, 4-(P) 4-AMINOPYRIDINE,REAGENT 4-AMINO PYRIDINE PYRIDIN-4-YLAMINE |
CAS | 504-24-5 |
EINECS | 207-987-9 |
InChI | InChI=1/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)/p+1 |
InChIKey | NUKYPUAOHBNCPY-UHFFFAOYSA-N |
Molecular Formula | C5H6N2 |
Molar Mass | 94.11 |
Density | 1.26 |
Melting Point | 155-158 °C (lit.) |
Boling Point | 273 °C (lit.) |
Flash Point | 156°C |
Water Solubility | Soluble in water(112 g/L at 20 deg C). Soluble in ethyl ether, benzene. Slightly soluble in ligroin. Very soluble in ethanol. Soluble in methanol, acetone, tetrahydrofuran, isopropanol, acetonitrile, |
Solubility | H2O: soluble50mg/mL, clear, colorless |
Vapor Presure | 0.046Pa at 25℃ |
Appearance | Crystalline Powder, Solid or Crystals |
Color | White to faint grey to light yellow |
Merck | 14,3933 |
BRN | 105782 |
pKa | 9.114(at 25℃) |
Storage Condition | 2-8°C |
Refractive Index | 1.5560 (estimate) |
Physical and Chemical Properties | Toxicity LD 50(mg/kg) traits from benzene in the precipitation of colorless needle-like crystals, ammonia odor. solubility slightly soluble in petroleum ether, soluble in water, ether and benzene, soluble in ethanol. |
Use | Used as pesticide, medicine and dye intermediates; Also used as chemical reagents. Synthesis of antibiotic drug 4-acetamidopiperidine acetate and other intermediates, but also the preparation of cardiotonic, bactericidal agents, antiarrhythmic drugs, antiulcer drugs and antispasmodic milverine raw materials; an important raw material of new antihypertensive drug pinacidil. |
Risk Codes | R28 - Very Toxic if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 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.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S37/39 - Wear suitable gloves and eye/face protection S28A - S1 - Keep locked up. |
UN IDs | UN 2671 6.1/PG 2 |
WGK Germany | 3 |
RTECS | US1750000 |
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: 21 mg/kg |
LogP | -0.76 at pH7.4 |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
biological activity | 4-Aminopyridine (4-AP, Fampridine, Dalfampridine) is an effective and non-selective voltage gated potassium channels (Kv) inhibitor. In CHO cells, the IC50s for Kv1.1 and Kv1.2 are 170 μM and 230 μM respectively. Obtained a hazardous chemicals business license |
Target | Value |
Kv1.4 () | 13 μM |
Kv3.1 () | 29 μM |
Kv3.2 () | 100 μM |
Kv1.3 () | 195 μM |
Kv1.1 () | 290 μM |
use | used in organic synthesis, can be used as a pharmaceutical intermediate. is an intermediate for the synthesis of antibiotic drugs |
Production method | Pyridine is oxidized with hydrogen peroxide, phthalic anhydride is added to phthalate, and then decomposed with dilute hydrochloric acid to make N-oxidized pyridine hydrochloride. N-oxypyridine hydrochloride is nitrated to produce N-oxy-4-nitropyridine. N-oxy-4-nitropyridine is reduced by iron powder to obtain 4-aminopyridine. Dissolve 1gN-oxy-4-nitropyridine (melting point 159 ℃) in 30ml of acetic acid, add 2.2g of iron powder, and the reaction starts immediately. After adding, keep the 100% for 1h and cool. After adding about 50ml of water to dilute, neutralize with 30% sodium hydroxide solution and adjust to strong alkaline, extract with ether 3 times, 100ml each time. The ether extract was combined and dried with anhydrous potassium carbonate. After the ether is evaporated, the crude 4-aminopyridine is distilled under reduced pressure. Recrystallization of the crude product from benzene or toluene-petroleum ether mixed solvent yields 0.6g of white needle crystal 4-aminopyridine with 90% yield. |
category | pesticide |
toxicity classification | highly toxic |
acute toxicity | oral-rat LD50: 21 mg/kg; Oral-mouse LD50: 42 mg/kg |
flammability hazard characteristics | open flame is combustible; high heat emits toxic nitrogen oxide gas |
storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidants, acids and food additives |
fire extinguishing agent | dry powder, foam, carbon dioxide, sand |
spontaneous combustion temperature | 640°C |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |