Pyridine N-oxide
Pyridine-N-oxide
CAS: 694-59-7
Molecular Formula: C5H5NO
Pyridine N-oxide - Names and Identifiers
| Name | Pyridine-N-oxide |
| Synonyms | pyridineoxide Pyridine oxide Pyridin-N-oxid 1-oxidePyridine PYRIDINE-1-OXIDE PYRIDINE-N-OXIDE pyridine 1-oxide Pyridine N-oxide Pyridine-N-oxide Pyridine-N-Oxidee |
| CAS | 694-59-7 |
| EINECS | 211-774-6 |
| InChI | InChI=1/C5H5NO/c7-6-4-2-1-3-5-6/h1-5H |
Pyridine N-oxide - Physico-chemical Properties
| Molecular Formula | C5H5NO |
| Molar Mass | 95.1 |
| Density | 1.1418 (rough estimate) |
| Melting Point | 62-67°C(lit.) |
| Boling Point | 270°C(lit.) |
| Flash Point | 143 °C |
| Water Solubility | soluble |
| Vapor Presure | 0.0116mmHg at 25°C |
| Appearance | Crystalline Solid, Crystals, and/or Chunks |
| Color | White to brownish |
| Merck | 14,7972 |
| BRN | 105257 |
| pKa | 0.79(at 24℃) |
| Storage Condition | 2-8°C |
| Sensitive | Hygroscopic |
| Refractive Index | 1.5939 (estimate) |
| MDL | MFCD00006194 |
| Physical and Chemical Properties | Colorless crystals |
Pyridine N-oxide - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed R40 - Limited evidence of a carcinogenic effect R20/21/22 - Harmful 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. S24/25 - Avoid contact with skin and eyes. S37/39 - Wear suitable gloves and eye/face protection S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S22 - Do not breathe dust. |
| WGK Germany | 3 |
| RTECS | UT6410000 |
| FLUKA BRAND F CODES | 21 |
| TSCA | Yes |
| HS Code | 29333999 |
Pyridine N-oxide - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Chemical reaction | pyridine N-oxide is a kind of stable organic compound, which can be used as a starting material to synthesize pyridine derivatives. The conversion of pyridine N-oxide to ortho-substituted alkyl pyridines using abundant and readily available olefins as alkylating agents is very attractive. However, there are only a few such reports and they are only applicable to electron-deficient olefins. For example, perfluoropropene and pyridine N-oxide are reacted by 1,3-dipolar cycloaddition and carbonyl fluoride elimination to obtain tetrafluoroethyl substituted pyridine (Fig. 1a,J. Org. Chem. 3343, 33, 3344-; Mendelev complexes., 16, 161-163). Although pyridine N-oxides contain polar N-O bonds, their 1,3-dipole activity is low for cycloaddition reactions, the reason for this may be that the aromaticity of both substrates is destroyed simultaneously in the reaction. One solution to this problem is to catalyze the free radical species of simple olefin formation as the alkylating component of the pyridine N-oxide. Because this kind of cationic radical has sufficient electrophilicity, it can be coupled with pyridine N-oxide to generate a radical intermediate, and then after the intramolecular ortho-addition and carbonyl compound elimination, ortho-substituted pyridine products can be obtained. Figure 1. Conversion of pyridine N-oxide to ortho-alkyl substituted pyridines (source: angelw. Chem. Int. Ed.) |
| production method | 1. Preparation of pyridine by peroxyphthalic acid oxidation. 2. In a 1 l Three-necked flask equipped with a stirrer, thermometer and dropping funnel, 110g (1.39 mol) of pyridine are placed, 250 (285G, 1.50 mol) of 40% peroxyacetic acid were added (10% or 20% peroxyacetic acid was also used). It takes 50-60 minutes to complete the procedure. Stirring was continued until the temperature of the mixture dropped to 40 ° C. When inspection of acetic acid with potassium iodide solution showed no peroxide, the acetic acid solution was evaporated on a water vapor bath and under water pump reduced pressure. The residue (180-190g) was distilled at a pressure of 1mm and the solid distillate was collected. The vacuum pump must be protected with a dry ice cold trap (about 60 ml of acetic acid produced by the dissociation of pyridine oxide acetate at low pressure may be collected in the cold trap). Heat in an oil bath and do not raise the temperature above 130 °c. This gave 103-110g (78-83%) of a colorless solid. |
Last Update：2024-04-09 15:16:52
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