15307-93-4
2,6-Dichlorodiphenylamine
CAS: 15307-93-4
Molecular Formula: C12H9Cl2N
15307-93-4 - Names and Identifiers
| Name | 2,6-Dichlorodiphenylamine |
| Synonyms | TIMTEC-BB SBB003229 2,6-dichlorobisaniline ,6-DICHLORODIPHENYLAMINE 2,6-DICHLORODIPHENYLAMINE 2,6-Dichlorodiphenylamine 2,6-dichloro diphenylamine N-Phenyl-2,6-dichloroaniline 2,6 Dichloro di phenol amine N-PHENYL-2,6-DICHLOROANILINE 2,6-dichloro-N-phenylaniline Benzenamine, 2,6-dichloro-N-phenyl- |
| CAS | 15307-93-4 |
| EINECS | 239-349-0 |
| InChI | InChI=1/C12H9Cl2N/c13-10-7-4-8-11(14)12(10)15-9-5-2-1-3-6-9/h1-8,15H |
| InChIKey | HDUUZPLYVVQTKN-UHFFFAOYSA-N |
15307-93-4 - Physico-chemical Properties
| Molecular Formula | C12H9Cl2N |
| Molar Mass | 238.11 |
| Density | 1.327±0.06 g/cm3(Predicted) |
| Melting Point | 50-53°C(lit.) |
| Boling Point | 115 °C(Press: 0.01 Torr) |
| Flash Point | >230°F |
| Solubility | Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) |
| Vapor Presure | 0.000625mmHg at 25°C |
| Appearance | Solid |
| Color | Pale brown |
| BRN | 2725987 |
| pKa | -2.57±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Sensitive | Sensitive to air |
| Refractive Index | 1.649 |
| MDL | MFCD00269648 |
| Physical and Chemical Properties | Liquid. Boiling point 109-111 °c/0.4. |
15307-93-4 - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/38 - Irritating to eyes and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S60 - This material and its container must be disposed of as hazardous waste. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| HS Code | 29214200 |
15307-93-4 - Reference Information
| Use | 2, 6-dichloro-N-phenylaniline is an analog of diclofenac, diclofenac is a non-steroidal anti-inflammatory compound, Is a decyclooxygenase (COX) inhibitor. An intermediate of diclofenac. |
| Biological activity | 2,6-Dichlorodiphenylamine is a structural analog of diclofenac sodium (HY-15037) with anti-Candida albicans activity. Diclofenac Sodium is an effective, non-selective anti-inflammatory agent and an inhibitor of COX. In CHO cells, the IC50 values for human COX-1 and COX-2 are 4 and 1.3 nM respectively. |
| production method | 1. preparation method N-phenyl -2,2,6,6, 6-tetrachlorocycloheximide (3): add 2,2,6,6, 6-tetrachlorocyclohexanone (2)100g(0.424mol), aniline 71g(0.763mol), glacial acetic acid 200mL into a reaction bottle equipped with a stirrer and a temperature group, the reaction was stirred at 45~50 ℃ for 6h. After cooling to room temperature, slowly pour into 300mL of ice water to separate the oil layer. The water layer was extracted with toluene (50mL × 3), the oil layer and toluene layer were combined, and then washed with saturated sodium bicarbonate, saturated salt water and water, and dried with anhydrous sodium sulfate. Retract the solvent under reduced pressure to obtain brown oil, and cure after cooling. Recrystallize with methanol, decolorize with activated carbon, and precipitate yellow crystals after cooling. Extraction filtration, drying, N-phenyl -2,2,6, 6-tetrachlorocycloheximide (3)123g, yield 93.5%,mp70~73 ℃. N-phenyl -2, 6-dichloroaniline (1): 100g(0.322mol) of the above compound (3) was added to a reaction bottle equipped with a stirrer and thermometer, DMF10mL, and stirred at 135~137 ℃ for 0.5h. Cold to room temperature, add 300mL of toluene, 150mL of water, and stir at room temperature for 30min. The organic layer is separated, the water layer is organic layer, the water layer is extracted with toluene, the organic layer is combined, the water is washed to neutral, and the anhydrous sodium sulfate is dried. Distillate the solvent under reduced pressure, and the remainder cools and solidifies. Recrystallization with methanol, decolorization of activated carbon, and precipitation of solid after cooling. Filtration, drying, yellow crystalline powder N-phenyl -2, 6-dichloroaniline (1)74g, yield 96.5%,mp51.5~53 ℃, literature value 49.5~50.7 ℃. [1] |
Last Update：2024-04-10 22:29:15
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