2-chloro-5-(chloromethyl)-1,3-thiazole
2-Chloro-5-Chloromethylthiazole
CAS: 105827-91-6
Molecular Formula: C4H3Cl2NS
2-chloro-5-(chloromethyl)-1,3-thiazole - Names and Identifiers
2-chloro-5-(chloromethyl)-1,3-thiazole - Physico-chemical Properties
| Molecular Formula | C4H3Cl2NS |
| Molar Mass | 168.04 |
| Density | 1.503±0.06 g/cm3(Predicted) |
| Melting Point | 31 |
| Boling Point | 268.6±32.0 °C(Predicted) |
| Flash Point | 116.3°C |
| Vapor Presure | 0.0126mmHg at 25°C |
| Appearance | White to pale yellow crystals or colorless liquids |
| BRN | 5861439 |
| pKa | 0.19±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,2-8°C |
| Refractive Index | n20/D1.571 |
| MDL | MFCD01073549 |
| Physical and Chemical Properties | This product is colorless liquid, m.p.30 ℃, B. p.108 ~ 110 ℃/2.4kPa, needle-like crystal at room temperature, insoluble in water, soluble in dichloromethane, chloroform, carbon tetrachloride and other solvents. |
| Use | Used as pesticide, pharmaceutical intermediates |
2-chloro-5-(chloromethyl)-1,3-thiazole - Risk and Safety
| Risk Codes | 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. R43 - May cause sensitization by skin contact R34 - Causes burns R24 - Toxic in contact with skin R22 - Harmful if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37 - Wear suitable gloves. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | 2922 |
| WGK Germany | 3 |
| HS Code | 29349990 |
| Hazard Note | Irritant |
| Hazard Class | 8 |
| Packing Group | Ⅱ |
2-chloro-5-(chloromethyl)-1,3-thiazole - Reference Information
| introduction | 2-chloro -5-chloromethylthiazole (CCMT for short) is a light yellow crystal or light yellow liquid with a content of ≥ 98% and a melting point of 29-31 ℃. It is a necessary intermediate for the synthesis of second-generation neonicotinoid insecticides such as thiamethoxam, thiacloprid, and chlorothioline. The mechanism of action of the second-generation neonicotinoid insecticides is similar to that of the first-generation neonicotinoid insecticides, but it has the advantages of lower dosage, wider insecticidal spectrum, and higher safety. Pests have a certain degree of control, and can process stems, leaves, soil, and seeds. |
| Synthesis method | Using 3-chloropropene as raw material: chlorine (or chlorine-producing compounds, such as sulfonyl chloride) and 1-isothiocyanate-2-propylene chloroform solution are simultaneously injected into the refluxed chloroform solution for reaction. The reaction requires excessive chlorine gas, with more side reactions, the purity of the crude product is 41.1%, the purity after simple distillation is only 47.8%, and the yield is 50.4%. 1-Isothiocyanate-2-propene can be prepared by reacting 3-chloropropene with sodium thiocyanate and rearranging. The reaction is as follows: |
| chemical properties | this product is colorless liquid, m.p.30 ℃, B. p.108 ~ 110 ℃/2.4kPa, needle crystal at room temperature, insoluble in water, soluble in dichloromethane, chloroform, carbon tetrachloride and other solvents. |
| use | 2-chloro -5-chloromethyl-thiazole is an intermediate of the insecticide thiamethoxam and thiacidamide. used as pesticide, pharmaceutical intermediates used in the synthesis of pesticides thiamethoxam, thiacidin, medicine ritonavir. At present, thiamethoxam, as a new generation of nicotine insecticide, has attracted the attention of the pesticide industry and has a good market prospect. Ritonavir, as an inhibitor of human immunodeficiency virus (HIV), is also indispensable in the absence of specific drugs |
| production method | its preparation method is to add 2-chloropropenyl isothiocyanate and solvent chloroform into the reaction bottle, then add thioyl chloride dropwise, keep the internal temperature at 30 ℃, then react at room temperature for 2.5h after dropping, at this time the internal temperature rises to 36 ℃, after the reaction is finished, the solvent and the remaining thioyl chloride are removed by distillation, the residue is dissolved in dichloromethane, and is washed and dried respectively with NaHCO3 solution and water, the product is obtained by steaming off the solvent (under reduced pressure). The reaction equation is shown in the figure. |
Last Update：2024-04-09 21:01:54
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