2,6-dichloro-4-Trifluoromethyllaniline
2,6-dichloro-4-(trifluoromethyl)aniline
CAS: 24279-39-8
Molecular Formula: C7H4Cl2F3N
2,6-dichloro-4-Trifluoromethyllaniline - Names and Identifiers
| Name | 2,6-dichloro-4-(trifluoromethyl)aniline |
| Synonyms | TIMTEC-BB SBB003283 4-Amino-3,5-dichlorobenzotrifluoride 3,5-Dichloro-4-Amino Benzotrifluoride 2,6-dichloro-(trifluoromethyl)aniline 3,5-DICHLORO-4-AMINO BENZOTRIFLUORIDE 2,6-Dichloro-4-trifluoromethylaniline 2,6-dichloro-4-Trifluoromethyllaniline 2,6-DICHLORO-4-(TRIFLUOROMETHYL)ANILINE 2,6-dichloro-4-(trifluoromethyl)aniline |
| CAS | 24279-39-8 |
| EINECS | 416-430-0 |
| InChI | InChI=1/C7H4Cl2F3N/c8-4-1-3(7(10,11)12)2-5(9)6(4)13/h1-2H,13H2 |
| InChIKey | ITNMAZSPBLRJLU-UHFFFAOYSA-N |
2,6-dichloro-4-Trifluoromethyllaniline - Physico-chemical Properties
| Molecular Formula | C7H4Cl2F3N |
| Molar Mass | 230.01 |
| Density | 1.532g/mLat 25°C(lit.) |
| Melting Point | 34-36°C(lit.) |
| Boling Point | 60-62°C1mm Hg(lit.) |
| Flash Point | 190°F |
| Solubility | soluble in Methanol |
| Vapor Presure | 0.241mmHg at 25°C |
| Appearance | powder to lump |
| Specific Gravity | 1.532 |
| Color | White to Orange to Green |
| BRN | 2838819 |
| pKa | -1.13±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.518 |
| Physical and Chemical Properties | Density 1.532 melting point 33-36°C boiling point 60-62°C (1 mmHg) flash point 87°C |
| Use | Used as a pesticide intermediate |
2,6-dichloro-4-Trifluoromethyllaniline - Risk and Safety
| Risk Codes | R20/22 - Harmful by inhalation and if swallowed. R38 - Irritating to the skin R43 - May cause sensitization by skin contact R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S24 - Avoid contact with skin. S37 - Wear suitable gloves. 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. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 3 |
| HS Code | 29214300 |
| Hazard Note | Toxic |
| Hazard Class | 9 |
| Packing Group | III |
2,6-dichloro-4-Trifluoromethyllaniline - Reference Information
| use | 2, 6-dichloro-4-trifluorotolamine is the key intermediate of pesticide fipronil. The chemical name of fipronil is 5-amino -3-cyano -1-(2, 6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinyl pyrazole, The trade name is Ruijinte. It is a highly effective insecticide developed by French Rhone-Planck Company from 1987 to 1989 and registered in my country in 1992. 2, 6-dichloro-4-trifluoromethylaniline is a key intermediate for the synthesis of raxide. It is a slightly yellow crystal that is easy to combine with acid to form corresponding salts. raxide (Fipronil) is a new pyrazole broad-spectrum insecticide successfully developed by French Rhone-Planck Company in 1989. 2, 6-dichloro-4-trifluoromethylaniline is an important intermediate of the insecticide fipronil. In addition, its diazonium salt can be condensed by itself or with other compounds, Used in the dye industry, etc. Used as pesticide intermediate |
| Synthesis method | Using 4-chlorotrifluoromethylbenzene as raw material, the product is prepared by two-step reaction of amination and chlorination. For example, the first step of amination disclosed by the World Patent WO2004037766 is to add 4-chlorotrifluoromethylbenzene, cuprous chloride, potassium fluoride, ammonia, and methanol to the autoclave in sequence, stir and raise the temperature to 190-200 ℃, and keep the temperature for 6 After hours, the 4-trifluoromethylaniline is distilled under reduced pressure to obtain 4-trifluoromethylaniline; the second step of chlorination is to dissolve 4-trifluoromethylaniline in glacial acetic acid, and react with chlorine at 60 ℃ to obtain the product. The first step amination reaction conversion rate of this method is very low. |
| preparation | preparation of 3-chloro -4-amino -5-nitrotrifluorotoluene 3,4-dichloro -5-nitrotrifluorotoluene 600Kg is added to the reaction kettle, the reaction kettle is closed, nitrogen is replaced, stirring is started, the temperature is gradually increased to 160 ℃, ammonia gas is gradually introduced, and when the amount of injection reaches 125Kg, the sample tube is sampled and detected 3,4-dichloro -5-nitrotrifluorotoluene is 0.5%, cooled to below 80 ℃, ammonia gas is emptied to the tail gas recovery device, 200Kg * 2 water is added to the reaction kettle, the organic layer is washed with saturated salt water, and then dehydrated under reduced pressure, resulting in 544Kg of material (99.2% content, 0.5% water content and 98.0% yield). Preparation of 2, 6-dichloro-4-trifluoromethylaniline Add 1200Kg of 3-chloro -4-amino -5-nitrotrifluoroluene to the chlorination kettle, close the reaction kettle, replace with nitrogen, start stirring, gradually raise the temperature to 50 ℃, gradually introduce chlorine gas, control the reaction temperature to 70-80 ℃, and when the feed amount reaches 407Kg, the sample tube samples and detects 3-chloro -4-amino -5-nitrotrifluoroluene 0.5%, cooling to below 30 ℃, emptying chlorine gas to tail gas recovery device, adding ammonia water 200Kg * 4 to the reactor, washing with water, dewatering under reduced pressure, and distilling under reduced pressure to obtain 1090Kg of material (content 99.0%, moisture 0.5%, yield 95.0%). |
| Production method | The preparation method is usually 4-trifluoromethylaniline as raw material to prepare 2, 6-dichloro-4-trifluoromethylaniline. Put 50.0g of 4-trifluoromethylaniline into a 500mL reaction bottle, add 100mL of glacial acetic acid, start stirring, raise the temperature to 60 ℃, pass chlorine gas, stop the reaction when the raw material is tracked by gas chromatography to ≤ 0.5%, and after cooling, filtration and washing with water, 68.5g of solid product is 2,6-dichloro-4-trifluoromethylaniline with a content of 98%. It can also be reacted with p-chlorotrifluorotoluene at 180 ℃ with dimethylformamide in the presence of alkali for 24h, and the product obtained is N,N-dimethyl p-trifluoromethylaniline, and then chlorine gas is passed under light to obtain the product. |
Last Update：2024-04-10 22:29:15
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