4-(4-HYDROXYPHENYL)BENZOIC ACID
4'-Hydroxybiphenyl-4-carboxylic acid
CAS: 58574-03-1
Molecular Formula: C13H10O3
4-(4-HYDROXYPHENYL)BENZOIC ACID - Names and Identifiers
| Name | 4'-Hydroxybiphenyl-4-carboxylic acid |
| Synonyms | AKOS BAR-1038 4-(4-CARBOXYPHENYL)-PHENOL 4-(4-HYDROXYPHENYL)BENZOIC ACID 4'-hydroxybiphenyl-4-carboxylate 4-Hydroxy-4-biphenylcarboxylic acid 4'-HYDROXYBIPHENYL-4-CARBOXYLIC ACID 4-hydroxybiphenyl-4'-carboxylic acid 4'-Hydroxybiphenyl-4-carboxylic acid 4'-HYDROXY-4-BIPHENYLCARBOXYLIC ACID 4'-Hydroxy-4-biphenylcarboxylic acid 4-HYDROXY-4'-BIPHENYLCARBOXYLIC ACID 4-HYDROXY-4'-BIPHENYLCARBOXYCLIC ACID 4'-HYDROXY-4,1'-BIPHENYL-1-CARBOXYLIC ACID 4'-HYDROXY[1,1'-BIPHENYL]-4-CARBOXYLIC ACID |
| CAS | 58574-03-1 |
| EINECS | 607-884-2 |
| InChI | InChI=1/C13H10O3/c14-12-7-5-10(6-8-12)9-1-3-11(4-2-9)13(15)16/h1-8,14H,(H,15,16)/p-1 |
4-(4-HYDROXYPHENYL)BENZOIC ACID - Physico-chemical Properties
| Molecular Formula | C13H10O3 |
| Molar Mass | 214.22 |
| Density | 1.1956 (rough estimate) |
| Melting Point | 295°C (dec.)(lit.) |
| Boling Point | 314.35°C (rough estimate) |
| Flash Point | 222.2°C |
| Solubility | almost transparency in hot Methanol |
| Vapor Presure | 8.08E-08mmHg at 25°C |
| Appearance | White powder |
| Color | Clear colorless to yellow |
| pKa | 4.29±0.10(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.5090 (estimate) |
| MDL | MFCD00059078 |
4-(4-HYDROXYPHENYL)BENZOIC ACID - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R37/38 - Irritating to respiratory system and skin. R36 - Irritating to the eyes |
| 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 S37 - Wear suitable gloves. |
| WGK Germany | 3 |
| HS Code | 29163990 |
4-(4-HYDROXYPHENYL)BENZOIC ACID - Reference Information
| Application | 4 '-hydroxybiphenyl-4-carboxylic acid is a white powdery chemical intermediate. In the field of chemical industry, it is the synthetic matrix of many important chemicals. But at the same time, because 4 '-hydroxybiphenyl-4-carboxylic acid can seriously stimulate the eyes, skin and respiratory tract of human body, 4'-hydroxybiphenyl-4-carboxylic acid is also a toxic powdery chemical intermediate. |
| preparation | synthesis of 4-acetoxybiphenyl (2) 40.00g(0.235mol) 4-hydroxybiphenyl was dissolved in 24.00 of pyridine under protection of nitrogen and cooling, and g(0.306mol) of acetyl chloride was added dropwise. After completion of dropwise addition and stirring at room temperature for 24h, the reaction solution was poured into 1500ml of ice water to precipitate a large amount of precipitate, and the crude product was washed with water by Suction filtration to obtain a beige solid. Recrystallized from n-hexane to give white crystals 45.83G. Yield 91.9%. m. P. 85-86 °c. Synthesis of 4 '-acetoxy-4-acetylbiphenyl (3) 67.92g(0.509mol) anhydrous aluminum chloride and 33.96g(0.433mol) dichloromethane were added dropwise to a ML three-necked flask. Solution of acetyl chloride in 20ml of dichloromethane the temperature was controlled at about 10 ° C. After stirring for 40min, a solution of 42.45g(0.20mol) of compound 2 in 80ml of dichloromethane was added dropwise. After the dropwise addition, stirring was continued for 21h at room temperature. The reaction solution was poured into ice water, stirred and separated. The aqueous layer was extracted with dichloromethane (50mL × 2). The combined dichloromethane layers were dried over anhydrous magnesium sulfate and concentrated to dryness under reduced pressure to obtain a crude product which was recrystallized from 87.6% ml of absolute ethanol to give colorless crystals in a yield of G. m. P. 124 °c. Synthesis of 4 '-benzyloxy-4-acetylbiphenyl (4) a 15.00 ml round-bottom flask was charged with 11.01g(0.059mol) of compound 3, g(0.087mol) of benzyl chloride, 3.90g of tetrabutylammonium bromide, 16.83g(0.30mol) of potassium hydroxide, 45ml of chlorobenzene and 75ml of water were stirred under reflux for 6h and cooled to room temperature. The solution was adjusted to pH with dilute hydrochloric acid and 40ml of water was added to neutral to distill off the chlorobenzene under reduced pressure. After cooling to room temperature, the crude product was washed with water by Suction filtration. To the obtained pale yellow solid, 90.0% of isopropanol was added, and the mixture was heated to boiling and filtered while hot to obtain white flaky crystals. m. P. 174 °c. 4 '-benzyloxy-4-biphenylcarboxylic acid 9.80g(0.032mol) of compound 4, 5.57g(0.139mol) of sodium hydroxide, 85ml of sodium hypochlorite solution (≥ 9%) was added dropwise with stirring under 14-dioxane. After the dropwise addition was completed, the temperature was raised to 38 ° C, stirred for 22h, then heated to 80 ° C, stirred for 1H, and then the pH of the solution was adjusted to 1 with dilute hydrochloric acid to precipitate a large amount of light yellow precipitate, which was suction filtered to dryness. To the crude product, 80ml of glacial acetic acid was added and heated 9.05G of pale yellow powder was obtained by boiling cooling and Suction filtration, and the yield was 93.0%. m.p.211 -212 °c. Synthesis of 4 '-hydroxybiphenyl-4-carboxylic acid (1) 4.15g(0.0136mol) of compound 5, 0.50g of 10% Pd/C, 50ml of NN-dimethylformamide was added to the reaction flask for hydrogenation for 4H, and then the Pd/C filtrate was removed by Suction filtration. The filtrate was poured into 85.8% of water to precipitate a white precipitate and was washed with water to obtain a white powder. 50g yield was. |
Last Update：2024-04-09 20:49:11
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Product Name: 4′-Hydroxy-4-biphenylcarboxylic acid Visit Supplier Webpage Request for quotationCAS: 58574-03-1
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Mobile: 18021002903
QQ: 3008007409
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