2-Chloro-5-picoline
2-Chloro-5-methylpyridine
CAS: 18368-64-4
Molecular Formula: C6H6ClN
2-Chloro-5-picoline - Names and Identifiers
| Name | 2-Chloro-5-methylpyridine |
| Synonyms | 6-CHLORO-3-PICOLINE 2-CHLORO-5-PICOLINE 2-Chloro-5-picoline 2-chloro-5-methylpyrdine 2-Chloro-5-methylpyridine 2-chloro-5-methyl-pyridin 2-CHLORO-5-METHYLPYRIDINE 6-CHLORO-3-METHYL PYRIDINE 2-chloro-5-methyl pyridine 2-CHLORO-5-PICOLINE 2-CHLORO-5-METHYLPYRIDINE 2-CHLORO-5-METHYLPYRIDINE (2-CHLORO-5-PICOLINE) |
| CAS | 18368-64-4 |
| EINECS | 418-050-0 |
| InChI | InChI=1/C6H6ClN/c1-5-2-3-6(7)8-4-5/h2-4H,1H3 |
| InChIKey | VXLYOURCUVQYLN-UHFFFAOYSA-N |
2-Chloro-5-picoline - Physico-chemical Properties
| Molecular Formula | C6H6ClN |
| Molar Mass | 127.57 |
| Density | 1.169 g/mL at 25 °C (lit.) |
| Melting Point | 97 ºC (30 MMHG) |
| Boling Point | 97 °C/30 mmHg (lit.) |
| Flash Point | 195°F |
| Water Solubility | Slightly soluble in water. |
| Vapor Presure | 0.736mmHg at 25°C |
| Appearance | Bright yellow liquid |
| Specific Gravity | 1.169 |
| Color | Clear light yellow to straw-yellow or light pink-orange |
| pKa | 0.54±0.10(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | n20/D 1.53(lit.) |
| MDL | MFCD00792460 |
| Physical and Chemical Properties | Light yellow liquid |
| Use | Used as a pesticide intermediate |
2-Chloro-5-picoline - Risk and Safety
| Risk Codes | R21/22 - Harmful in contact with skin and if swallowed. R38 - Irritating to the skin R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S23 - Do not breathe vapour. S25 - Avoid contact with eyes. S36/37 - Wear suitable protective clothing and gloves. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 2 |
| RTECS | US6740000 |
| HS Code | 29333999 |
2-Chloro-5-picoline - Reference Information
| Use | Used as a pesticide intermediate 2-chloro-5-methylpyridine is an intermediate of imidacloprid and acetamiprid, referred to as monochloride, used to synthesize the next intermediate 2-chloro-5-chloromethylpyridine. |
| production method | there are many synthesis methods of 2-chloro-5-methylpyridine. according to the different raw materials used, there are mainly the following three routes. Using N-benzyl-N-acrylylacetamide as raw material, N-benzyl-N-acrylylacetamide and phosphorus oxychloride were stirred and reacted at 100 ℃ for 16h to obtain 2-chloro-5-methylpyridine with 67.5% yield. Aminopyridine is used as raw material. The methanol solution of 2-amino-5-methylpyridine is first saturated with hydrogen chloride, and then the mixture of methyl nitrite and hydrogen chloride is introduced to obtain 2-chloro-5-methylpyridine. Methyl nitrite can also be replaced by nitroso chloride or chlorobenzene as a solvent. Using 3-methylpyridine-N-oxide as raw material. Depending on the chlorinating agent used, there are four different ways to choose from. Phosphorus oxychloride is used as chlorinating agent. 3-methylpyridine-N-oxide reacts with phosphorus oxychloride in the presence of an organic base to produce 2-chloro-5-methylpyridine, and has a by-product 2-chloro-3-methylpyridine. Add a certain amount of 3-methylpyridine-N-oxide and solvent into the reaction kettle, add phosphorus oxychloride and organic phosphorus at -10 ℃, after dropping, react at -2 ℃ for 5h, hydrolyze, desolvate, distill to obtain crude products, and then freeze and crystallize to obtain fine monochloride. COCl2 can also be used instead of POCl3 as chlorinating agent. N,N-diethylamino phosphorus oxychloride as chlorinating agent. At room temperature, a dichloromethane solution containing 2-chloro-5-methylpyridine-N-oxide was treated with N,N-diethylaminooxyphosphorus and diisopropylamine dissolved in dichloromethane to obtain a mixture containing 2-chloro-5-methylpyridine-82%, 2-chloro-3-methylpyridine-12% in 83% yields. Phthalyl chloride is used as chlorinating agent. Phthalyl chloride was added dropwise to a mixture containing 3-methylpyridine-N-oxide, triethylamine and dichloromethane for reaction to obtain a mixture containing 2-chloro-5-methylpyridine 84% and 2-chloro-3-methylpyridine 16% with 85% yields. Organic salt is used as intermediate. 2-chloro-5-methylpyridine can also be prepared from n-propionaldehyde, methyl acrylate and morpholine. At present, some domestic enterprises also adopt this method. |
Last Update：2024-04-09 20:48:19
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