TL 1473
4,7-Dichloroquinoline
CAS: 86-98-6
Molecular Formula: C9H5Cl2N
TL 1473 - Names and Identifiers
| Name | 4,7-Dichloroquinoline |
| Synonyms | tl1473 TL 1473 Sulfate Impurity 4,7-Dichloroquinone Amobiquine Impurity 1 4,7-dichloro-quinolin 4,7-DICHLOROQUINOLINE 4,7-Dichloroquinoline Hydroxychloroquine Sulfate EP Impurity G |
| CAS | 86-98-6 |
| EINECS | 201-714-7 |
| InChI | InChI=1/C9H5Cl2N/c10-6-1-2-7-8(11)3-4-12-9(7)5-6/h1-5H |
| InChIKey | HXEWMTXDBOQQKO-UHFFFAOYSA-N |
TL 1473 - Physico-chemical Properties
| Molecular Formula | C9H5Cl2N |
| Molar Mass | 198.05 |
| Density | 1.4178 (rough estimate) |
| Melting Point | 81-83 °C (lit.) |
| Boling Point | 298.4 °F (148°C) |
| Flash Point | 164 °C |
| Water Solubility | insoluble |
| Solubility | chloroform: soluble50mg/mL, clear, colorless to greenish-yellow |
| Vapor Presure | 0.103Pa at 25℃ |
| Appearance | Crystallization |
| Color | White to pale brown |
| BRN | 125359 |
| pKa | 1.99±0.27(Predicted) |
| Storage Condition | 2-30°C |
| Refractive Index | 1.6300 (estimate) |
| MDL | MFCD00006774 |
| Physical and Chemical Properties | Needle-like crystals. The melting point of 93 deg C, boiling point of 148 deg C (1.33kPa). |
| Use | As a drug chloroquine phosphate intermediate |
TL 1473 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system 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. S22 - Do not breathe dust. |
| WGK Germany | 3 |
| RTECS | VB4200000 |
| TSCA | Yes |
| HS Code | 29334910 |
| Hazard Note | Irritant |
TL 1473 - Reference Information
| LogP | 3.193 at 25℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | 4, 7-dichloroquinoline is a white needle-like crystalline solid with a melting point of 84-86°C, it is an important pharmaceutical intermediate and a raw material for the synthesis of hydroxychloroquine sulfate, a drug for the treatment of discoid lupus erythematosus and systemic lupus erythematosus. |
| Application | 4, 7-dichloroquinoline is an important intermediate of antimalarial drugs such as chloroquine phosphate, hydroxychloroquine sulfate and amodiaquine, it is usually obtained by chlorination and isolation of 7-chloro-4-hydroxyquinoline. |
| preparation | 300g of toluene, 5g of N,N-dimethylformamide, 5g of triphenylphosphine oxide, 7-chloro-4-hydroxyquinoline 100g, stirring was started, and the temperature was raised to 50-100 °c. 23% G of toluene solution of triphosgene was prepared, completely dissolved, and then placed in a constant pressure dropping funnel. The temperature in the reaction flask was maintained at 50 ° C. To 100 ° C., and 23% triphosgene toluene solution was slowly added dropwise, and the dropwise addition time was controlled to be 1 to 8 hours. After completion of the dropwise addition, the reaction was continued until the completion of the reaction was monitored by TLC (about 1-3 hours for completion of the reaction). After completion of the reaction, the reaction was distilled under reduced pressure at 50 ° C. To 100 ° C., and the distillation was stopped after the distillation was performed under reduced pressure until there were no obvious droplets in the condenser. 300g of anhydrous ethanol and 1-5g of activated carbon were added under stirring, and the temperature was raised to reflux for decolorization for 1 hour. Filter the filtrate while hot, then cool down to 10 ℃ ~ 30 ℃ to filter the filter cake, the filter cake is washed with 10~50g anhydrous ethanol, and the wet product is dried at 60 ℃ under reduced pressure to obtain 4, 7-dichloroquinoline. |
| Use | 4, 7-dichloroquinoline is used in the synthesis of hybrid aminoquinoline-triazine derivatives with antimicrobial activity. In addition, it is also used in the synthesis of novel oxazolidinones as antimicrobial agents, showing effective efficacy against common bacterial strains. Chloroquinoline impurity. used as a drug intermediate of chloroquine phosphate |
| production method | is obtained by chlorination of 7-chloro-4-hydroxyquinoline. |
Last Update：2024-04-09 15:16:53
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