156-06-9
phenylpyruvic acid
CAS: 156-06-9
Molecular Formula: C9H8O3
156-06-9 - Names and Identifiers
156-06-9 - Physico-chemical Properties
| Molecular Formula | C9H8O3 |
| Molar Mass | 164.16 |
| Density | 1.257±0.06 g/cm3(Predicted) |
| Melting Point | 150-154 °C (lit.) |
| Boling Point | 299.1±19.0 °C(Predicted) |
| Flash Point | 148.9°C |
| JECFA Number | 1479 |
| Solubility | Soluble in alcohol, ether, benzene and other solvents |
| Vapor Presure | 0.000546mmHg at 25°C |
| Appearance | White crystal. |
| Color | White to Light yellow |
| BRN | 2207312 |
| pKa | 2.61±0.54(Predicted) |
| Storage Condition | -20°C |
| Sensitive | Light & Air Sensitive & Hygroscopic |
| MDL | MFCD00002589 |
156-06-9 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 3-8-10-23 |
| HS Code | 29183000 |
156-06-9 - Nature
Open Data Verified Data
White Crystal, melting point 158~160 °c. Soluble in alcohol, ether, benzene and other solvents.
Last Update：2024-01-02 23:10:35
156-06-9 - Preparation Method
Open Data Verified Data
- The benzyl chloride method is obtained from the catalytic carbonylation of benzyl chloride.
- a-acetyl amino cinnamic acid method from a acetyl amino cinnamic acid hydrolysis. The yield of this method can reach 88% ~ 94%.
Last Update：2022-01-01 10:43:41
156-06-9 - Application
Open Data Verified Data
It can be used as a raw material for the synthesis of L-phenylalanine, and can also be used for the preparation of sweet element (asapatinib), Food Nutrition Fortifier and various anticancer drugs.
Last Update：2025-08-19 16:24:40
156-06-9 - Reference Information
| FEMA | 3892 | 2-OXO-3-PHENYLPROPIONIC ACID |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Biological activity | 2-Oxo-3-phenylpropanoic acid (Phenylpyruvic acid) is used to synthesize phenyl lactic acid. |
| use | intermediate of ketophenylalanine calcium. |
| production method | 3. preparation method: 2-methyl -4-phenylmethylene -5-oxo -4,5-dihydrooxazole (3): add acetoaminoacetic acid (2)58.5g(0.5mol) and anhydrous sodium acetate 30g(0.37mol) into a 1L reaction bottle, 79g(0.74mol) of newly distilled benzaldehyde and 134g of 95% acetic anhydride are installed in a reflux condenser and shaken and warmed for 10~20min. Let it dissolve. Then reflux reaction for 1h. Leave overnight in the refrigerator after cooling. The yellow solid is treated with 125mL of cold water, crushed, pumped and filtered, washed with cold water, and dried in a vacuum dryer containing phosphorus pentoxide to obtain 69-72g of crude compound (3), mp148 -150 ℃, and the yield is 74%-77%. No further purification is required, and the next reaction is directly used. A- acetylaminocinic acid (4): find the one in a 1L reaction bottle and add 47g(0.25mol),450mL acetone and 175mL water to the above compound (3), heat and reflux for 4 hours. After steaming out most of the acetone, add 400mL of water and continue to reflux for 5min to complete hydrolysis. Filter, filter residue washed with hot water twice. Merge filtrate and washing liquid, and decolorize activated carbon. Place in the refrigerator overnight, filter, wash with water, and dry at 90~100 ℃ to obtain colorless needle-like crystals (4)41~46g,mp191~192 ℃, and yield 80% ~ 90%. Phenylpyruvic acid (1): add compound (4)10g(0.05mol),200 mL1mol/L hydrochloric acid into a 500mL round bottom flask, heat and boil for 3 hours. If there is a small amount of light green oil, it can be filtered and removed. Cooling, precipitating crystallization. Suction filtration, cold water washing, combined filtrate and washing liquid, ether extraction 4 times, 50mL each time. The ether is steamed out to obtain part of the solid. The solids obtained twice were combined and dried in a vacuum dryer containing calcium chloride and sodium hydroxide to obtain compound (1)7.2~7.7g,mp150~154 ℃, and the yield was 88% ~ 94%. [1] |
Last Update：2024-04-09 02:00:07
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