95-73-8 - Names and IdentifiersName2,4-DichlorotolueneSynonyms2,4-DCT2,4-DICHLOROTOLUENE2,4-Dic
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| Name | 2,4-Dichlorotoluene |
| Synonyms | 2,4-DCT 2,4-DICHLOROTOLUENE 2,4-Dichlorotoluene Toluene, 2,4-dichloro- 2,4-dichloromethylbenzene 2,4-DICHLOROMETHYLBENZENE 2,4-dichloro-1-methylbenzene 1,3-DICHLORO-4-METHYLBENZENE 2,4-dichloro-1-methyl-benzen Benzene,2,4-dichloro-1-methyl- 2,4- Dichloro toluene |
| CAS | 95-73-8 |
| EINECS | 202-445-8 |
| InChI | InChI=1/C7H6Cl2/c1-5-2-3-6(8)4-7(5)9/h2-4H,1H3 |
| Molecular Formula | C7H6Cl2 |
| Molar Mass | 161.03 |
| Density | 1.246 g/mL at 25 °C (lit.) |
| Melting Point | -14 °C |
| Boling Point | 200 °C (lit.) |
| Flash Point | 175°F |
| Water Solubility | immiscible |
| Vapor Presure | 4 hPa (50 °C) |
| Appearance | Liquid |
| Color | Clear colorless |
| BRN | 1931691 |
| Storage Condition | Store below +30°C. |
| Refractive Index | n20/D 1.546(lit.) |
| Physical and Chemical Properties | Appearance:colorless transparent liquidMelting Point:-13.5℃Boiling Point:196-197℃relative density:1.249refractive index:1.548flash point:79℃Other:insoluble in water, soluble in alcohol, acetone |
| Use | Used as pesticides, dyes, pharmaceutical intermediates, used in the production of 2,4-dichlorobenzaldehyde, drug apheping, abdominal acid, etc |
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S23 - Do not breathe vapour. S24/25 - Avoid contact with skin and eyes. |
| UN IDs | UN 2810 |
| WGK Germany | 2 |
| RTECS | XT0730000 |
| TSCA | Yes |
| HS Code | 29036990 |
| Hazard Note | Harmful |
| Hazard Class | 9 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 2400 mg/kg |
| uses | used as pesticides, dyes, pharmaceutical intermediates, used in the production of 2, 4-dichlorobenzaldehyde, drug altepine, besilate and so on 2, 4-dichlorotoluene is an intermediate of bactericide diniconazole alcohol and benzylchlorotriazole alcohol, and is also a raw material for preparing 2, 4-dichlorobenzaldehyde. raw materials for organic synthesis, used in the pharmaceutical industry for the manufacture of antimalarial drugs, abamcinolone acid synthesis. For pesticide intermediates, manufacturing 2, 4-dichlorobenzyl chloride, 2, 4-dichlorobenzoyl chloride, also for the manufacture of 2, 4-dichlorobenzoic acid. |
| production method | There are two synthesis methods. 1.2, 4-dichlorotoluene method with 2, 4-diaminotoluene as raw material, by diazotization and chlorination. First, hydrochloric acid and water are put into the reaction Pan, heated to 50 ℃, dissolved in 2, 4-diaminotoluene under stirring, then hydrochloric acid and cuprous chloride are put into the pan, and 1% sodium nitrite solution is added uniformly, the temperature was maintained at about 60 ℃, and the layers were separated. The lower crude product was washed with water until neutral, alkali was added to alkaline, and then washed with water to remove alkali, A water vapor distillation was performed to obtain a finished product. 2.3-chloro -4-toluidine method by diazotization reaction with sodium nitrite, and then with copper chloride for sandemeier reaction. There are several preparation methods. P-chlorotoluene method p-chlorotoluene and catalyst ZrCl4 are put into the reactor, chlorine gas is passed for chlorination reaction, the amount of chlorine gas is controlled until the end of the reaction, the reaction is stopped, and the obtained reactant contains 2,4-dichlorotoluene 85.1%, if the chlorination reaction is carried out at 10~15 C with FeCl3 as the catalyst, the relative density of the solution is 1.025, and the product is 2, 4-dichlorotoluene and 3,4-dichlorotoluene, two component mass ratio is 100: 30. After chlorination, wash with water to neutral, and treat with 10% NaOH solution at 100~110 ℃ to remove other impurities. The treated chloride is subjected to distillation separation in a high efficiency distillation column (2,4-dichlorotoluene B. P. 200 °c, 3, 4-dichlorotoluene B. P. 207 °c). The yields of 2, 4-dichlorotoluene and 3, 4-dichlorotoluene were 64.4% and 9.8%, respectively. O-chlorotoluene method O-chlorotoluene is chlorinated at 142~196 ℃ with sulfuryl chloride as chlorinating agent. Products include 2, 4-dichlorotoluene and 2, 3-dichlorotoluene, and unreacted raw materials, their compositions were 55%, 6% and 39%, respectively. After distillation (2, 4-dichlorotoluene B. P. 200 °c, 2, 3-dichlorotoluene B. P. 207-208 ℃, O-chlorotoluene B. P. 157-159 °c) 2, 4-dichlorotoluene was isolated. O-nitrotoluene chlorination of O-nitrotoluene in the presence of FeCl3 catalyst at 35~40 ℃, When the relative density of the reactant reaches 1.320(15 ℃), the material is washed to neutral, and the reactant contains 15% of the raw material, 49% of 2-chloro-6-nitrotoluene and 21% of 4-chloro-2-nitrotoluene, there are more than 15% chlorides, after distillation and crystallization, 2-chloro-6-nitrotoluene and 4-chloro-2-nitrotoluene were obtained, the yield was 50% and 30% respectively, 4-chloro-2-nitrotoluene 4-chloro-2-aminotoluene was obtained by hydrogenation reduction reaction and steam distillation, and then diazotization and Sandmeyer reaction were carried out by adding CH2Cl2 to obtain 2, 4-dichlorotoluene. This process is used for the production of 2-chloro-6-nitrotoluene, the by-product 4-chloro-2-nitrotoluene for the herbicide quinclorac intermediate. 2, 4-diaminotoluene method 2, 4-diaminotoluene was subjected to diazotization reaction in the presence of NaNO2 and hydrochloric acid, followed by Sandmeyer reaction in the presence of Cu2Cl2 to obtain 2, 4-dichlorotoluene. 3-chloro-4-methylaniline method 3-chloro-4-methylaniline and hydrochloric acid were added to the reaction kettle, and then NaNO2 aqueous solution was added dropwise at 3~5 ℃, and the addition was completed within 2~3H, the diazotization reaction was carried out, and then the diazotization solution was added dropwise to a hydrochloric acid solution containing Cu2Cl2 at 2 to 5 ° C. For Sandmeyer reaction to obtain 2, 4-dichlorotoluene. In the above methods, P-chlorotoluene and O-chlorotoluene are used as raw materials to generate chlorides with many impurities and similar boiling points, and high-efficiency distillation column shall be used for fractionation, More than 98% of 2, 4-dichlorotoluene was obtained. These two methods are difficult to operate, and the cost of equipment investment is large. 2, 4-diaminotoluene method is not suitable for industrialization, and the basic principle of preparing 2, 4-dichlorotoluene by O-nitrotoluene method and 3-chloro-4-methylaniline method is the same, both are by diazotization and Sandmeyer reaction, there is a disadvantage of more wastewater. 2-chloro-6-nitrotoluene was produced by the O-nitrotoluene method and further reduced to obtain 2-chloro-6-aminotoluene, which is an important intermediate for production of quinclorac. |
| category | toxic substances |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 2400 mg/kg; Oral-mouse LD50: 2400 mg/kg |
| flammability hazard characteristics | open flame flammability; Toxic chloride fumes from combustion |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored separately from oxidants and food additives |
| fire extinguishing agent | foam, carbon dioxide, water mist, sand. |
| spontaneous combustion temperature | >450°C |
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