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 
• 492-38-6 2-phenylacrylic acid 
• 20102-12-9 2-hydroxy-2-phenylpropionitrile 
• 585-71-7 (1-bromoethyl)benzne 
• 873-73-4 4-n-chlorophenylacetylene 
• 201230-82-2 carbon monoxide 
• 118778-90-8 5-Methyl-2-[1-methyl-2-oxo-2-phenyl-eth-(E)-ylidene]-5-phenyl-[1,3]dithiolan-4-one 
• 1857-74-5 2,3-diphenylbutane 
• 124-38-9 carbon dioxide 
• 1123-85-9 (RS)-2-phenyl-1-propanol 
• 60014-86-0 (2,2-dibromo 1-methylethenyl)benzene 
• 672-65-1 (1-chloroethyl)benzene 
• 103-82-2 phenylacetic acid 

Downstream Products

• 56946-52-2 9-(1-phenyl-ethyl)-acridine 
• 31469-26-8 1,1-bis(trimethylsilyloxy)-2-phenylpropene 
• 109092-58-2 2-Methyl-2-phenyl-3-p-tolyl-propionsaeure 
• 59697-79-9 3-Hydroxy-2,3-dimethyl-2-phenyl-buttersaeure 
• 107402-31-3 4-(N-Benzoylamino)-2-methyl-2-phenylbutanoic acid 
• 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 
• 83247-38-5 2',6'-Dihydroxy-4'-methoxy-3'-methyl-2-phenylpropiophenon 
• 83247-39-6 2,4-Dihydroxy-6-methoxy-3,5-bis(2-phenylpropionyl)toluol 
• 156025-60-4 N-Hydroxy-N-methyl-2-phenyl-propionamide 
• 104435-84-9 3-Methoxy-4-[6-(2-phenyl-propionylamino)-indol-1-ylmethyl]-benzoic acid methyl ester 
• 492-37-5 (+)-α-phenylpropionic acid 
• 492-37-5 (-)-2-phenylpropanoic acid 
• 137074-81-8 1-(2-phenylpropanoyl)-4-(pyridin-3-ylcyanomethyl)piperazine 

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.

Dynamic Kinetic Resolution of I-Substituted Cyclic β-Ketoesters via Asymmetric Hydrogenation: Constructing Chiral Cyclic β-Hydroxyesters with Three Contiguous Stereocenters

An efficient asymmetric hydrogenation of racemic I-substituted cyclic β-ketoesters via dynamic kinetic resolution to provide chiral cyclic β-hydroxy esters with three contiguous stereocenters is reported. Using a chiral spiro iridium catalyst (R)-5 (Ir-SpiroSAP), a series of racemic I-Aryl/alkyl substituted cyclic β-ketoesters were hydrogenated to the corresponding chiral cyclic β-hydroxy esters in high yields (84-97%) with good to excellent enantioselectivities (69->99% ee) and cis,cis-selectivities (up to >99:1).

Insertion of Diazo Esters into C-F Bonds toward Diastereoselective One-Carbon Elongation of Benzylic Fluorides: Unprecedented BF3Catalysis with C-F Bond Cleavage and Re-formation

Selective transformation of C-F bonds remains a significant goal in organic chemistry, but C-F insertion of a one-carbon-atom unit has never been established. Herein we report the BF3-catalyzed formal insertion of diazo esters as one-carbon-atom sources into C-F bonds to accomplish one-carbon elongation of benzylic fluorides. A DFT calculation study revealed that the BF3 catalyst could contribute to both C-F bond cleavage and re-formation. This elongation provided α-fluoro-α,β-diaryl esters with a high level of diastereoselectivity. Various benzylic fluorides and diazo esters were applicable. The synthetic utility of this method was demonstrated by the synthesis of a fluoro analogue of a compound that is used as a transient receptor and potential canonical channel inhibitor.