Fluotrimazol
Fluotrimazol
CAS: 31251-03-3
Molecular Formula: C22H16F3N3
Fluotrimazol - Names and Identifiers
Fluotrimazol - Physico-chemical Properties
| Molecular Formula | C22H16F3N3 |
| Molar Mass | 379.38 |
| Density | 1.21±0.1 g/cm3(Predicted) |
| Melting Point | 132°C |
| Boling Point | 485.6±55.0 °C(Predicted) |
| Storage Condition | 2-8℃ |
| Physical and Chemical Properties | The pure chemical product is white crystal. The solubility at m.p.132 ℃ and 20 ℃ is dichloromethane 40%, cyclohexanone 20%, toluene 10%, propylene glycol 5%, water 1.5mg/L. Decomposed in 0.2mol/L sulfuric acid solution and stabilized in 0.1mol/L sodium hydroxide solution. |
| Use | Use 1. Fluorine-containing azole fungicides. It is characterized by high biological activity, low toxicity, and has special effects on cucumber, peach, barley, grape and other powdery mildew. 2, fluorine triazole because of containing fluorine atoms, high biological activity, reduce the toxicity of cucumber, barley, grape and other powdery mildew control has special effects. 3, for efficient, broad-spectrum fungicides, cucumber, peach, grape, barley, sugar beet and other crops powdery mildew has special effects |
Fluotrimazol - Upstream Downstream Industry
| Raw Materials | Diethyl ether Formamide METHYL CHLORIDE Benzophenone Benzotrifluoride 2,4-Dihydroxybenzophenone Triphenylmethanol |
Fluotrimazol - Nature
| morphology | neat |
| acidity coefficient (pKa) | 2.15±0.10(Predicted) |
| BRN | 8395848 |
| NIST chemical information | Fluotrimazol(31251-03-3) |
Last Update：2024-04-10 22:29:15
Fluotrimazol - Uses and synthesis methods
Toxicity
the acute oral LD50 in rats is 5000mg/kg, and the acute percutaneous LD50 is> 1000mg/kg. The 90-day feeding test was 800mg/kg for rats and 5000mg/kg for dogs. Safe for bees.
production method
1. Using m-brominated trifluorotoluene as the starting material, Grignard reagent is formed, and then nucleophilic addition is carried out with benzophenone, and then hydrolyzed with ammonium chloride to obtain 3-trifluoromethyl triphenylmethanol. Then continue to react with concentrated hydrochloric acid to produce 3-trifluoromethyltriphenylchloromethane, and finally use triethylamine as the acid binding agent, and N,N-dimethylformamide as the solvent, under the protection of nitrogen, and 1,2, 4-triazole reaction to obtain fluorotriazole. (1) Put 4.8g of magnesium chips and small iodine into a reaction flask, drop 30ml of anhydrous ether solution containing m-brominated trifluorotoluene (4.5g of m-brominated trifluorotoluene dissolved in 100ml of anhydrous ether), and warm it in a water bath. Slowly drop the remaining m-brominated trifluorotoluene anhydrous ether solution under stirring, add it, reflux for 30min, evaporate the ether, cool, and drop the benzene solution containing benzophenone (36g benzophenone dissolved in 150ml benzene). After dropping, heat reflux for 2h, cooling, dropping in an aqueous solution containing 40g of ammonium chloride to decompose the product, separate the benzene layer, debenzene, dehydrate, distillation under reduced pressure, and collect 180-184 ℃(0.08kPa) fractions. Let it stand and cool to obtain a colorless mass with a melting point of 50-52°C, which is 3-trifluoromethyl triphenylmethanol. (2) shake 32g of 3-trifluoromethyl triphenylmethanol, 15.6g of benzene and 22g of concentrated hydrochloric acid together until the mass is completely dissolved. Then the benzene layer is separated, dried, and debenzene to obtain a light yellow oil, which is 3-trifluoromethyltriphenylchloromethane. (3) 34.6g,1,2,4-triazole 7g, 250ml of N,N-dimethylformamide and 11g of triethylamine were added to the reaction bottle, and heated to 93-100 ℃ for 3h under the protection of nitrogen. The desolubilization residue was washed with water and then extracted with dichloromethane. The extract is dried and evaporated to remove methylene chloride to obtain a light yellow solid. Fluorotriazole was obtained by recrystallization with acetone, melting point 128-130 ℃. Prepare 50% wettable powder, 125g/L emulsifiable concentrate.
2, preparation of 3-trifluoromethyl triphenylmethanol 0.2mol of m-brominated trifluorotoluene is dissolved in 100mL of anhydrous ether, 30mL is added dropwise to a reaction bottle containing 0.2mol of magnesium chips and a small particle of iodine, and then warm it in a water bath to start the reaction. The remaining m-bromotrifluorotoluene is then slowly dropped and the reaction bottle is cooled with cold water. After dropping, heat and reflux with cold water bath for 30min, so that magnesium chips can completely act. Evaporate ether, cool, drop anhydrous benzene solution containing benzophenone (0.2mol benzophenone +150mL benzene), drop after heating and reflux for 2 hours. Cooling, dropping ammonium chloride saturated aqueous solution (containing NH4Cl 40g) to hydrolyze the product, separate the benzene layer, extract the water layer, merge the benzene layer, evaporate the benzene, steam distillation, the resulting brown-red viscous substance is reduced to water, and 180~184 ℃/80Pa fraction is collected. 49% yield. After the oil is placed, it forms a massive crystal of 3-trifluoromethyl triphenylmethanol.
preparation of 3-trifluoromethyltriphenylchloromethane 0.1mol of the previous product and 15.6g of benzene are mixed, then 0.22mol of concentrated hydrochloric acid is added, shaken to dissolve the alcohol, and the benzene layer is separated. the hydrochloric acid layer is extracted with benzene, the benzene layer is combined, the benzene layer is dried and steamed to obtain the light yellow oily product 3-trifluoromethyltriphenylchloromethane, which can be directly.
The synthesis of trifluorobenzazole uses DMF as solvent and triethylamine as acid binding agent. Under the protection of nitrogen, 3-trifluoromethyltriphenylchloromethane reacts with 1,2, 4-triazole to obtain trifluorobenzazole. The operation process is as follows: 0.1mol, 1,2, 4-triazole 0.1mol, 250mL of N,N-dimethylformamide and 11.0g of triethylamine are reacted at 90~100 ℃ for 3h under the protection of nitrogen, decompressed and desolamated, the residue is washed with hydrogen chloride with water, then extracted with dichloromethane and dried with anhydrous magnesium sulfate to obtain light yellow solid. Recrystallized with acetone to obtain white crystals. The total yield of 2 and 3 steps is 55%.
Last Update：2024-04-09 21:00:56
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Raw Materials for Fluotrimazol