7782-26-5

Basic information

• Product Name: (R)-(-)-2-Phenylpropionic acid
• Synonyms: (R)-(-)-2-PHENYLPROPIONIC ACID;(R)-2-PHENYLPROPIONIC ACID;(R)-HTA;(R)-(-)-HYDRATROPIC ACID;(R)-(-)-PHENYLPROPIONIC ACID;(R)-(-)-alpha-Methylphenylaceticacid;(R)-(-)-2-Phenylpropionicacid,97%;(r)-(-)-à-methylphenylacetic acid
• CAS NO: 7782-26-5
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• Product Categories: Carbonic Acid;Chiral Compounds;chiral;Analytical Chemistry;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination
• Mol File: 7782-26-5.mol
• Article Data: 156

Chemical Properties

• Melting Point: 29-30 °C(lit.)
• Boiling Point: 115 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Beige to slightly brown/Low Melting Solid or Liquid
• Density: 1.1 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.523(lit.)
• Storage Temp.: 2-8°C
• PKA: 4.34±0.10(Predicted)
• BRN: 2207688
• CAS DataBase Reference: (R)-(-)-2-Phenylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-2-Phenylpropionic acid(7782-26-5)
• EPA Substance Registry System: (R)-(-)-2-Phenylpropionic acid(7782-26-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 7782-26-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

Chiral building block. Resolving agent

Definition

ChEBI: The (R)-enantiomer of hydratropic acid.

Purification Methods

Purify the acids by vacuum distillation and by recrystallisation from pet ether. The S-anilide has m 103-104o (from H2O or CHCl3/*C6H6), [] D +47o (c 9, Me3CO) [Argus & Kenyon J Chem Soc 916 1939, Campbell & Kenyon J Chem Soc 25 1946, Levene et al. J Biol Chem 88 27, 34 1930]. [Beilstein 9 III 2417, 9 IV 1779.]

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

Upstream product

• 492-37-5 hydratropic acid 
• 64-17-5 ethanol 
• 492-38-6 2-phenylacrylic acid 
• 75-64-9 tert-butylamine 
• 25145-43-1 2-phenylpropionyl chloride 
• 67-63-0 isopropyl alcohol 
• 2510-99-8 ethyl 2-phenylpropanoate 
• 51117-40-9 (R)-2-chloro-2-phenyl-propionic acid 
• 64-19-7 acetic acid 
• 1445-91-6 (S)-1-phenylethanol 
• 143-33-9 sodium cyanide 
• 4513-94-4 1H-pyrrole-2-carbonitrile 
• 3156-07-8 methyl phenyl ketene 
• 1059200-51-9 (4S)-3-((2R)-2-phenylpropionyl)-4,5,5-triphenyl-oxazolidin-2-one 

Downstream Products

• 2510-99-8 ethyl (R)-2-phenylpropionate 
• 2510-99-8 (-)-Ethyl hydrotropate 
• 17609-56-2 (2R*)-2-Phenyl-N-((1R*)-1-phenylethyl)propanamide 
• 142793-67-7 (R)-2-Phenyl-propionic acid (1R,2R)-2-fluoro-1-p-tolylsulfanylmethyl-pent-4-enyl ester 
• 142793-69-9 (R)-2-Phenyl-propionic acid (1R,2S)-2-fluoro-1-p-tolylsulfanylmethyl-pent-4-enyl ester 
• 144788-22-7 (R)-2-Phenyl-propionic acid (1R,2S)-1-(chloro-difluoro-methyl)-2-p-tolylsulfanyl-pent-4-enyl ester 
• 144788-18-1 (R)-2-Phenyl-propionic acid (1R,2R)-1-(chloro-difluoro-methyl)-2-p-tolylsulfanyl-pent-4-enyl ester 
• 144788-20-5 (R)-2-Phenyl-propionic acid (1S,2S)-1-(chloro-difluoro-methyl)-2-p-tolylsulfanyl-pent-4-enyl ester 
• 144788-16-9 (R)-2-Phenyl-propionic acid (1S,2R)-1-(chloro-difluoro-methyl)-2-p-tolylsulfanyl-pent-4-enyl ester 
• 116505-04-5 (R)-(-)-2-phenylpropionyl bromide 
• 82826-58-2 (R)-N-Hydroxy-2-phenyl-propionamide 

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.

Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids

Asymmetric hydroxycarbonylation is one of the most fundamental yet challenging methods for the synthesis of carboxylic acids. Herein, we reported the development of a palladium-catalyzed highly enantioselective Markovnikov hydroxycarbonylation of vinyl arenes with CO and water. A monodentate phosphoramidite ligand L6 plays vital role in the reaction. The reaction tolerates a range of functional groups, and provides a facile and atom-economical approach to an array of 2-arylpropanoic acids including several commonly used non-steroidal anti-inflammatory drugs. The catalytic system has also enabled an asymmetric Markovnikov hydroalkoxycarbonylation of vinyl arenes with alcohols to afford 2-arylpropanates. Mechanistic investigations suggested that the hydropalladation is irreversible and is the regio- and enantiodetermining step, while hydrolysis/alcoholysis is probably the rate-limiting step.

Enantioselective Enzymatic Reduction of Acrylic Acids

An ene-reductase (ERED 36) with broad substrate specificity was identified, and optimization studies led to the development of an enzymatic protocol for the reduction of α,β-unsaturated acids under mild, aqueous conditions. The substrate scope includes aromatic- A nd aliphatic-substituted acrylic acids, as well as cyclic α,β-substituted acrylic acids, yielding chiral α-substituted acids with exquisite levels of enantioselectivity (>99% ee).