492-37-5

Basic information

• Product Name: DL-2-Phenylpropionic acid
• Synonyms: Benzeneacetic acid, .alpha.-methyl-;(n)-2-phenylpropionic acid;(n)-à-methylphenylacetic acid;2-HENYLPROPIONIC ACID;2-PHENYLPROPINICACID;dl-PPA;α-methyl-α-toluic acid;2-PHENYLPROPIONIC ACID 98%
• CAS NO: 492-37-5
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• EINECS: 207-752-0
• Product Categories: Aliphatics;Carboxylic Acids;Organic acids;Carboxylic Acids;Pharmaceutical Intermediates
• Mol File: 492-37-5.mol
• Article Data: 238

Chemical Properties

• Melting Point: 5 °C
• Boiling Point: 260-262 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear pale yellow to yellow/Liquid
• Density: 1.1 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00601mmHg at 25°C
• Refractive Index: n20/D 1.522(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 9.9g/l
• PKA: 4.34±0.10(Predicted)
• Water Solubility: 10 g/L (20 ºC)
• BRN: 1863558
• CAS DataBase Reference: DL-2-Phenylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2-Phenylpropionic acid(492-37-5)
• EPA Substance Registry System: DL-2-Phenylpropionic acid(492-37-5)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 492-37-5(Hazardous Substances Data)

Usage

Chemical Properties

clear pale yellow to yellow liquid

Uses

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/ja00443a033The Journal of Organic Chemistry, 51, p. 4354, 1986 DOI: 10.1021/jo00373a005Tetrahedron Letters, 21, p. 581, 1980 DOI: 10.1016/S0040-4039(01)85562-3

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.]

InChI:InChI=1/C9H10O2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-7H,1H3,(H,10,11)/t7-/m0/s1

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 79-21-0 peracetic acid 
• 34713-70-7 2-Phenylpropanal 
• 20102-12-9 2-hydroxy-2-phenylpropionitrile 
• 16052-39-4 3-(2′-phenylpropionyloxy)tropane 
• 585-71-7 (1-bromoethyl)benzne 
• 100-42-5 styrene 
• 144-62-7 oxalic acid 
• 103-82-2 phenylacetic acid 
• 74-88-4 methyl iodide 
• 98-83-9 isopropenylbenzene 
• 81616-82-2 N,N-dimethyl-2-phenylpropionamide 
• 47004-02-4 2-phenyl-propionic acid nortropan-3-yl ester 
• 3990-44-1 2-phenyl-propionic acid 9-methyl-(1rN,2tH,4tH,5cN)-3-oxa-9-aza-tricyclo[3.3.1.0^2,4]non-7t-yl ester 

Downstream Products

• 31508-44-8 2-phenylpropionic acid methyl ester 
• 57780-74-2 2-phenylpropanoyl 2-phenylpropanoate 
• 56946-52-2 9-(1-phenyl-ethyl)-acridine 
• 4370-81-4 3-hydroxy-2-methyl-2-phenylpropanoic acid 
• 65569-15-5 5-Chloro-N-(2-diethylamino-ethyl)-2-methoxy-4-(2-phenyl-propionylamino)-benzamide 
• 109092-58-2 2-Methyl-2-phenyl-3-p-tolyl-propionsaeure 
• 107402-32-4 4-(3,3-Diethyl-ureido)-2-methyl-2-phenyl-butyric acid 
• 107402-34-6 2-Methyl-2-phenyl-4-(2-phenyl-propionylamino)-butyric acid 
• 107402-33-5 4-{1-[2-(3,3-Diethyl-ureido)-ethyl]-3,3-diethyl-ureido}-2-methyl-2-phenyl-butyric acid 
• 241818-32-6 (4S,1'RS)-4,5-dihydro-4-(1-methylethyl)-2-(1-phenylethyl)oxazole 
• 98876-60-9 (4S,1'S)-4-(1-Methylethyl)-2-(1-phenylethyl)-4,5-dihydrooxazole 
• 98876-61-0 (4S,1'R)-4-(1-Methylethyl)-2-(1-phenylethyl)-4,5-dihydrooxazole 
• 4371-02-2 2-methyl-2-phenylmalonic acid 
• 83243-96-3 2,2-Difluor-5,7-dimethoxy-8-methyl-4-(2-phenylethyl)-1-oxa-3-oxonia-2-boratanaphthalin 

Relevant articles and documents

Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel-Catalyzed Cascade Reactions: Facile Synthesis of Profens

We report a stereoselective conversion of terminal alkynes to α-chiral carboxylic acids using a nickel-catalyzed domino hydrocarboxylation-transfer hydrogenation reaction. A simple nickel/BenzP* catalyst displayed high activity in both steps of regioselective hydrocarboxylation of alkynes and subsequent asymmetric transfer hydrogenation. The reaction was successfully applied in enantioselective preparation of three nonsteroidal anti-inflammatory profens (>90 % ees) and the chiral fragment of AZD2716.

Catalytic α-Deracemization of Ketones Enabled by Photoredox Deprotonation and Enantioselective Protonation

This study reports the catalytic deracemization of ketones bearing stereocenters in the α-position in a single reaction via deprotonation, followed by enantioselective protonation. The principle of microscopic reversibility, which has previously rendered this strategy elusive, is overcome by a photoredox deprotonation through single electron transfer and subsequent hydrogen atom transfer (HAT). Specifically, the irradiation of racemic pyridylketones in the presence of a single photocatalyst and a tertiary amine provides nonracemic carbonyl compounds with up to 97% enantiomeric excess. The photocatalyst harvests the visible light, induces the redox process, and is responsible for the asymmetric induction, while the amine serves as a single electron donor, HAT reagent, and proton source. This conceptually simple light-driven strategy of coupling a photoredox deprotonation with a stereocontrolled protonation, in conjunction with an enrichment process, serves as a blueprint for other deracemizations of ubiquitous carbonyl compounds.

A direct synthesis of carboxylic acidsviaplatinum-catalysed hydroxycarbonylation of olefins

The platinum-catalysed hydroxycarbonylation of olefins is reported for the first time. Using a combination of PtCl2/2,2′-bis(tert-butyl(pyridin-2-yl)phosphanyl)-1,1′-binaphthalene (Neolephos) in the presence of sulfuric acid [0.6 M] in acetic acid selective carbonylation of terminal aliphatic olefins proceeds to good yields and selectivities to the corresponding carboxylic acids. Comparing the reactivity of different butenes (iso- andn-butenes), the terminal olefin can be selectively carbonylated.