2-PHENYLPROPIONIC ACID
Synonym(s):(±)-2-Phenylpropionic acid;(±)-Hydratropic acid
- CAS NO.：492-37-5
- Empirical Formula: C9H10O2
- Molecular Weight: 150.18
- MDL number: MFCD00002650
- EINECS: 207-752-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-18 17:01:59
What is 2-PHENYLPROPIONIC ACID?
Chemical properties
clear pale yellow to yellow liquid
The Uses of 2-PHENYLPROPIONIC ACID
2-Phenylpropionic acid is used in the preparation of ibuprofen derivatives for their anti-inflammatory activity. Also used in nucleation inhibitors in Dutch resolution of diastereomers.
Definition
ChEBI: A 2-arylpropionic acid carrying a phenyl group at position 2. It is a metabolite of alpha-methylstyrene (AMS), a volatile hydrocarbon.
Synthesis Reference(s)
Journal of the American Chemical Society, 99, p. 182, 1977 DOI: 10.1021/ja00443a033
The Journal of Organic Chemistry, 51, p. 4354, 1986 DOI: 10.1021/jo00373a005
Tetrahedron Letters, 21, p. 581, 1980 DOI: 10.1016/S0040-4039(01)85562-3
Synthesis
2-Phenylpropionic acid is prepared:
1) from Benzyl cyanide by Metbylation with
Methyl iodide and Sodamide to produce alpha-Phenylpropionitrile, from which the
acid is produced by acid hydrolysis.
2) from Acetophenone cyanhydrin with Hydriodic
acid.
Purification Methods
Fractionally distil the acid, or recrystallise it from pet ether (b 40-60o) with strong cooling (see references below). [Beilstein 9 II 348.]
Properties of 2-PHENYLPROPIONIC ACID
| Melting point: | 5 °C |
| Boiling point: | 260-262 °C (lit.) |
| Density | 1.1 g/mL at 25 °C (lit.) |
| refractive index | n |
| Flash point: | >230 °F |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | 9.9g/l |
| form | Liquid |
| pka | 4.34±0.10(Predicted) |
| color | Clear pale yellow to yellow |
| PH | 3 (5g/l, H2O, 20℃) |
| Water Solubility | 10 g/L (20 ºC) |
| BRN | 1863558 |
| CAS DataBase Reference | 492-37-5(CAS DataBase Reference) |
| NIST Chemistry Reference | Benzeneacetic acid, «alpha»-methyl-(492-37-5) |
| EPA Substance Registry System | Benzeneacetic acid, .alpha.-methyl- (492-37-5) |
Safety information for 2-PHENYLPROPIONIC ACID
| Signal word | Danger |
| Pictogram(s) |
 Corrosion Corrosives GHS05 |
| GHS Hazard Statements |
H314:Skin corrosion/irritation |
| Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
Computed Descriptors for 2-PHENYLPROPIONIC ACID
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