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HomeProduct name list2-PHENYLPROPIONIC ACID

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: 2024-07-16 18:25:32
2-PHENYLPROPIONIC ACID Structural

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  n20/D 1.522(lit.)
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)
ghs
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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