24065-33-6
5-Chloro-2-thiophenecarboxylic acid
CAS: 24065-33-6
Molecular Formula: C5H3ClO2S
24065-33-6 - Names and Identifiers
| Name | 5-Chloro-2-thiophenecarboxylic acid |
| Synonyms | AKOS B000092 Rivaroxaban Impurity N Chlorothiophene-2-carboxy 2-Chlorothiophene-5-formicacid 5-chlorothiophene-2-carboxylate 5-chloro-2-thiophenecarboxylicaci 5-CHLORO-2-THIOPHENECARBOXYLIC ACID 2-chlorothiophene-5-carboxylic acid 5-Chloro-2-thiophenecarboxylic acid 5-Chlorothiophene-2-carboxylic acid 5-CHLOROTHIOPHENE-2-CARBOXYLIC ACID 5-Chlorothiophene-2-carboxilic acid 5-Chloro-2-thiophene carboxylic acid 2-Thiophenecarboxylic acid, 5-chloro- |
| CAS | 24065-33-6 |
| EINECS | 000-000-0 |
| InChI | InChI=1/C5H3ClO2S/c6-4-2-1-3(9-4)5(7)8/h1-2H,(H,7,8)/p-1 |
| InChIKey | QZLSBOVWPHXCLT-UHFFFAOYSA-N |
24065-33-6 - Physico-chemical Properties
| Molecular Formula | C5H3ClO2S |
| Molar Mass | 162.59 |
| Density | 1.466 (estimate) |
| Melting Point | 154-158°C(lit.) |
| Boling Point | 287.0±20.0 °C(Predicted) |
| Flash Point | 127.4°C |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Vapor Presure | 0.00119mmHg at 25°C |
| Appearance | White solid |
| Color | Cream-yellow |
| BRN | 118361 |
| pKa | 3.32±0.10(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| MDL | MFCD00041426 |
24065-33-6 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36 - Irritating to the eyes R43 - May cause sensitization by skin contact R36/37/38 - 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. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | XM8400000 |
| HS Code | 29349990 |
| Hazard Class | IRRITANT |
24065-33-6 - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| Overview | 2-chlorothiophene-5-formic acid is a pharmaceutical intermediate that can be used to prepare rivaroxaban's intermediate 5-chlorothiophene-2-formyl chloride. Rivaroxaban, whose English name is Rivaroxaban, is a new oral anticoagulant. It has a long-term effect through oral absorption. It is used to prevent and treat venous thrombosis. It has a wide range of treatment and does not require routine coagulation function monitoring. The world's first direct factor Xa inhibitor developed for Bayer was approved for listing by the U.S. Food and Drug Administration (FDA) in 2011. |
| Application | 2-chlorothiophene-5-formic acid white solid powder, anti-inflammatory antibacterial drugs for livestock, mainly used for the treatment of chicken, rabbit, sheep coccidiosis (cecum coccidiosis), chicken cholera and typhoid; It is an intermediate of rivaroxaban, an API for adult patients undergoing elective hip or knee replacement surgery to prevent venous thrombosis (VTE); rivaroxaban intermediate. |
| use | 2-chlorothiophene-5-formic acid is an intermediate in organic synthesis and pharmaceutical, mainly used as an intermediate of rivaroxaban, an API for preventing venous thrombosis (VTE) in laboratory research and development and chemical pharmaceutical synthesis. anti-inflammatory and antibacterial drugs for livestock, mainly used to treat chicken, rabbit, sheep coccidiosis (cecal coccidia), chicken cholera and typhoid disease rivaroxaban intermediate |
| Preparation | Step 1: The preparation of 5-chlorothiophene-2-formaldehyde is connected to a 1-liter dry four-mouth bottle with stirring, thermometer, condenser tube and constant pressure drip funnel, Add 200 grams of N,N-dimethylformamide (DMF), 118.5 grams (1.0 moles) of 2-chlorothiophene, heat, and keep the internal temperature between 40-60 ℃, slowly drip 169g (1.1 mol) of phosphorus oxychloride from the constant pressure drop funnel, after dropping, stir at 95-100 ℃ for 2 hours. Cool to 20°C, pour the reaction liquid into a beaker filled with 400 grams of crushed ice and 400 grams of water, and then neutralize it with a 30% sodium hydroxide solution to a pH of 6-7, and separate the oil layer, and the water layer Use dichloromethane to extract 3 times, use 300 grams of dichloromethane each time, combine the dichloromethane layer with the separated oil layer, wash the organic phase once with 50 grams of water, distill the organic phase to recover dichloromethane, and then reduce the pressure Distillation, 141.5g 5-chlorothiophene-2-formaldehyde was obtained with 96.6% yield and 99.97% GC purity. Step 2: Preparation of 2-chlorothiophene-5-formic acid To a 500 ml four-mouth bottle with stirring and thermometer, add 200 grams of dichloromethane, 29.5 grams (0.2 moles) of 5-chlorothiophene-2-formaldehyde, 30 grams of 30% hydrogen peroxide, and stir for 6 hours between 25 and 30 degrees. Stratified, the water layer is extracted with dichloromethane for 3 times, 50 grams of dichloromethane each time, the dichloromethane layer is combined, the organic phase is washed once with 20 grams of 5% sodium sulfite aqueous solution, the organic phase is distilled to recover dichloromethane, and the residue is recrystallized with petroleum ether to obtain 30.5 grams of white solid 2-chlorothiophene-5-formic acid, the yield is 93.8%, and the HPLC purity is 99.98%. |
Last Update：2024-04-09 20:52:54
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