2-Carboxy-4-chloroanisole
5-chloro-O-anisic acid
CAS: 3438-16-2
Molecular Formula: C8H7ClO3
2-Carboxy-4-chloroanisole - Names and Identifiers
| Name | 5-chloro-O-anisic acid |
| Synonyms | Glyburide IMP RARECHEM AL BO 0576 5-chloro-O-anisic acid 5-CHLORO-2-ANISIC ACID 2-Carboxy-4-chloroanisole 5-chloro-2-methoxybenzoate 5-CHLORO-2-METHOXYBENZOIC ACID 2-METHOXY-5-CHLOROBENZOIC ACID 5-chloro-2-methoxybenzoic acid 5-Chloro-N-(2-phenylethyl)-2-MethoxybenzaMide |
| CAS | 3438-16-2 |
| EINECS | 222-343-7 |
| InChI | InChI=1/C8H7ClO3/c1-12-7-3-2-5(9)4-6(7)8(10)11/h2-4H,1H3,(H,10,11)/p-1 |
2-Carboxy-4-chloroanisole - Physico-chemical Properties
| Molecular Formula | C8H7ClO3 |
| Molar Mass | 186.59 |
| Density | 1,259g/cm |
| Melting Point | 98-100 °C (lit.) |
| Boling Point | 150-152C |
| Flash Point | 140.9°C |
| Solubility | Chloroform, Methanol |
| Vapor Presure | 0.000276mmHg at 25°C |
| Appearance | White-like crystalline powder |
| Color | White to off-white |
| pKa | 3.72±0.10(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1,544-1546 |
| MDL | MFCD00017546 |
2-Carboxy-4-chloroanisole - 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. S37/39 - Wear suitable gloves and eye/face protection S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| HS Code | 29189900 |
| Hazard Note | Irritant |
2-Carboxy-4-chloroanisole - Reference Information
| Application | 5-chloro-2-methoxybenzoic acid as an intermediate for the synthesis of glibenclamide. Glibenclamide, as a hypoglycemic agent, is suitable for mild to moderate type II diabetes with unsatisfactory effect of diet control alone. The pancreatic islet B cells of patients have certain insulin secretion function and no serious complications. |
| preparation | method 1. adding 350kg of 30% sodium hydroxide solution and 30kg of 5-chlorosalicylic acid into the reaction tank in sequence, stirring evenly, adding 85kg of dimethyl sulfate dropwise, heating to 30 ℃, reacting for 3 hours, heating to 98 ℃, refluxing for 4 hours, acidification with 30% hydrochloric acid to pH = 5, stir for 1 hour, add 30% hydrochloric acid to continue acidification to pH = 2, consume 40kg of hydrochloric acid in total, stir for 2 hours, and filter to obtain 5-chlorine -2-methoxybenzoic acid wet product, place the wet product in an oven, and dry at 35 ℃ to obtain 27.7kg of 5-chlorine -2-methoxybenzoic acid crude product with a yield of 85.40%. Methods 2. adding 76g(0.5mol) of o-methoxybenzoic acid and 100ml of dichloromethane into a 500ml reaction bottle, stirring to dissolve it, controlling the temperature at 10~15 ℃ and adding 81g(0.6mol) of thioyl chloride dropwise for chlorination, keeping the temperature at 10~15 ℃ for 10min after the thioyl chloride dropwise addition, adding 200ml of water for washing, dividing out an organic phase, and evaporating dichloromethane under reduced pressure to obtain 87.7g of 5-chloro -2-methoxybenzoic acid, 175g of 50% alcohol recrystallized and dried to obtain 84.9g of white crystal. Yield ≥ 91%. Quality index: appearance: white crystal, melting point: 98.5~100.2 ℃, content: ≥ 99.5%(HPLC). |
| use | pharmaceutical intermediates. |
| production method | salicylic acid is obtained by chlorination and methylation. Dissolve salicylic acid in chlorobenzene, and pass chlorine at 55-80 ℃ under the irradiation of fluorescent lamp. End of chlorination, cooling, filtration, drying, 5-chlorosalicylic acid. Add it into sodium hydroxide solution, add dimethyl sulfate dropwise under stirring, and add sodium hydroxide solution to make the pH of the reaction solution 10-12 and keep the temperature below 35 ℃. After the addition, keep the temperature at 26-35 ℃ for 8 hours. Filter while hot, adjust the pH of the filtrate to 2-3 with 15% hydrochloric acid, cool, filter, wash, and dry to obtain 5-chloro-2-methoxybenzoic acid. |
Last Update：2024-04-09 19:05:11
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Product Name: 5-Chloro-2-Methoxybenzoic Acid Visit Supplier Webpage Request for quotationCAS: 3438-16-2
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Mobile: 18021002903
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