5650-40-8

Basic information

• Product Name: 2-hydroxypropiophenone
• Synonyms: 2-Hydroxypropiophenone; AI3-20420; 1-Propanone, 2-hydroxy-1-phenyl-; 2-hydroxy-1-phenylpropan-1-one
• CAS NO: 5650-40-8
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.1745
• EINECS: 227-091-1
• Mol File: 5650-40-8.mol
• Article Data: 186

Chemical Properties

• Boiling Point: 251.8°C at 760 mmHg
• Flash Point: 103.8°C
• Density: 1.109g/cm³
• Vapor Pressure: 0.0105mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 2-hydroxypropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxypropiophenone(5650-40-8)
• EPA Substance Registry System: 2-hydroxypropiophenone(5650-40-8)

Safety Data

• Hazardous Substances Data: 5650-40-8(Hazardous Substances Data)

Usage

General Description

2-Hydroxypropiophenone, also known as α-hydroxypropiophenone or α-benzoylpropionic acid, is a chemical compound with the molecular formula C9H10O2. This aromatic ketone is commonly used as an intermediate in the production of pharmaceuticals and perfumes. It is also used as a flavoring agent in the food industry. 2-Hydroxypropiophenone is a white crystalline solid with a melting point of 56-57°C and a boiling point of 284°C. It is soluble in alcohol and ether, and slightly soluble in water. 2-Hydroxypropiophenone has potential applications in the fields of medicine, fragrance, and food.

Upstream product

• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 78-97-7 2-hydroxy-propionitrile 
• 21894-15-5 (2S,3R)-2-Chloro-2-methyl-3-phenyl-oxirane 
• 97-64-3 ethyl 2-hydroxypropionate 
• 6493-83-0 2-methoxy-1-phenyl-propan-1-one 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 1855-09-0 1-phenyl-1,2-propandiol 
• 164577-21-3 2,2,5-trimethyl-4-phenyl-1,3-dioxolane 
• 103-65-1 phenylpropane 
• 98-88-4 benzoyl chloride 
• 141-78-6 ethyl acetate 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 75-07-0 acetaldehyde 
• 6084-15-7 2-iodo-1-phenylpropan-1-one 

Downstream Products

• 20907-13-5 2-methyl-1-phenylpropane-1,2-diol 
• 90925-49-8 2-phenyl-2,3-butanediol 
• 52183-00-3 1,1-diphenylpropane-1,2-diol 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 6493-83-0 2-methoxy-1-phenyl-propan-1-one 
• 91190-30-6 Trifluoro-methanesulfonic acid 1-methyl-2-oxo-2-phenyl-ethyl ester 
• 21120-36-5 1-fluoroethyl phenyl ketone 
• 1855-09-0 1-phenyl-1,2-propandiol 
• 91791-26-3 (+/-)-(E)-2-hydroxy-1-phenyl-1-propanone oxime 
• 91791-27-4 (+/-)-(Z)-2-hydroxy-1-phenyl-1-propanone oxime 
• 88196-06-9 syn-1-phenylpropane-1,2-diol 
• 40421-52-1 (1RS,2SR)-1-phenylpropane-1,2-diol 
• 5650-40-8 (S)-2-hydroxypropiophenone 
• 5650-40-8 (R)-2-hydroxy-1-phenylpropan-1-one 

Relevant articles and documents

Carboligation reactions mediated by benzoylformate decarboxylase immobilized on a magnetic solid support

In this study, magnetic nanoparticles (Fe3O4, magnetite) with immobilized metal affinity ligands (MSS) were prepared and characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), fourier transform infrared spectroscopy (FTIR), and vibrating-sample magnetometer (VSM) methods for purification and immobilization of the histidine-tagged recombinant benzoylformate decarboxylase (BFD). The MSS support was shown to be eligible for selective binding of HIS-tagged BFD by SDS-page analysis. Loading capacity of the MSS support was determined as 43.6 ± 1.1 mg/g. The regeneration ability for protein binding was also studied. An immobilized BFD was tested to catalyze benzoin condensation and representative cross acyloin reaction. Conversion and enantiomeric excess values were comparable with that of free enzyme catalyzed reactions. Chirality 25:415-421, 2013.

Asymmetric oxidation of silyl enol ethers using chiral dioxiranes derived from α-fluoro cyclohexanones

Asymmetric oxidation of silyl enolethers derived from tetralone, 2-methyl-tetralone, propiophenone and deoxybenzoin using chiral dioxiranes generated in situ from oxone and new chiral α-fluorinated cyclohexanones or fructose-derived ketone have been studied. It was observed that tetrasubstituted silyl enolethers are poor substrates, that substitution at C8 of the fluoro-ketones has a significant effect on the enantioselectivities obtained and that the fructose-derived-ketone provides higher enantioselectivities. The absolute configuration of the major hydroxy ketones obtained can be rationalized using a spiro model proposed for epoxidation of olefins.

Covalent immobilization of benzoylformate decarboxylase from Pseudomonas putida on magnetic epoxy support and its carboligation reactivity

Epoxy attached magnetic nanoparticles were prepared and used as solid support for covalent immobilization and stabilization of benzoylformate decarboxylase (BFD, E.C. 4.1.1.7) from Pseudomonas putida. A three-step immobilization/stabilization procedure is applied. The enzyme is firstly covalently immobilized under mild experimental conditions (e.g. pH 7.0, no added MgSO4 and 20 C). Secondly, the enzyme is immobilized under more drastic conditions (higher pH values, higher ionic strengths, etc.) to facilitate an increase in effective concentration of the enzyme on the support near the epoxide reactive sites. Thirdly, the remaining epoxy groups are blocked to stop any additional interaction between the enzyme and the support. With more drastic conditions, the loading of enzyme can be increased from 1.25 to 6.70 mg enzyme per gram of support. The covalently bounded enzyme was characterized in terms of its activity and stability for the formation of (S)-2-hydroxypropiophenone (2-HPP). The activity of the immobilized BFD was determined to be 53.0% related to the activity of the free enzyme. The immobilized biocatalyst retained 95% of its original activity after five reaction cycles.

Fluorescence spectroscopy as a novel method for on-line analysis of biocatalytic C-C bond formations

On-line analysis of bioprocesses is of increasing interest avoiding the time delay for off-line sample preparation and the following analyses via chromatographic methods. Moreover, continuous monitoring of the reaction components during chemo- or biocatalytic transformations provides a direct control of the process. Since productivity of the processes can be controlled simultaneously, on-line monitoring of the processes is attractive for industrial applications. The reliable in situ monitoring of biocatalyzed reactions has been a challenge where reactions run in aqueous solutions. Limited work has been published on the use of spectroscopic methods for on-line analysis of biocatalytic reactions up to now. However, in this communication two dimensional (2D)-fluorescence spectroscopy has been proved to be an effective tool for on-line monitoring of the carboligation reactions catalyzed by wild type benzoylformate decarboxylase (BFD) from Pseudomonas putida. BFD is a thiamine diphosphate (ThDP)-dependent enzyme that catalyzes the asymmetric C-C bond formation to (S)-2-hydroxypropiophenone ((S)-2-HPP) starting from benzaldehyde and acetaldehyde. The analysis of the fluorescence spectra was achieved by chemometric modeling performing principle component analysis (PCA) and partial least square (PLS) regression. The derived chemometric models were used for the validation of concentrations of yielded 2-HPP and the substrate benzaldehyde with low root mean square error of calibration (RMSEC).

Carboligation reactivity of benzaldehyde lyase (BAL, EC 4.1.2.38) covalently attached to magnetic nanoparticles

Epoxy-functionalized Fe3O4-SiO2 core-shell magnetic nanoparticles (epoxy-M-support) were prepared by modification with glycidyloxypropyltrimethoxysilane (GPTMS) and characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), and fourier transform infrared spectroscopy (FTIR) methods. Pure histidine-tagged recombinant benzaldehydelyase (BAL, EC 4.1.2.38) was efficiently immobilized onto the epoxy-M-support with covalent binding. An immobilized BAL epoxy-M-support system was tested to catalyze the self and cross condensation reactions of aldehydes, and the kinetic resolution of racemic acyloins. The acyloin products were obtained in high yield and with high enantiomeric excesses (≥98% ee). The carboligation reactivity of the immobilized enzyme was comparable to that of free enzyme-catalyzed reactions. The covalent immobilization offers high enzyme activity and stability (at least 5 repeats without losing its activity).

Heterofunctional Magnetic Metal-Chelate-Epoxy Supports for the Purification and Covalent Immobilization of Benzoylformate Decarboxylase from Pseudomonas Putida and Its Carboligation Reactivity

In this study, the combined use of the selectivity of metal chelate affinity chromatography with the capacity of epoxy supports to immobilize poly-His-tagged recombinant benzoylformate decarboxylase from Pseudomonas putida (BFD, E.C. 4.1.1.7) via covalent attachment is shown. This was achieved by designing tailor-made magnetic chelate-epoxy supports. In order to selectively adsorb and then covalently immobilize the poly-His-tagged BFD, the epoxy groups (300 μmol epoxy groups/g support) and a very small density of Co2+-chelate groups (38 μmol Co2+/g support) was introduced onto magnetic supports. That is, it was possible to accomplish, in a simple manner, the purification and covalent immobilization of a histidine-tagged recombinant BFD. The magnetically responsive biocatalyst was tested to catalyze the carboligation reactions. The benzoin condensation reactions were performed with this simple and convenient heterogeneous biocatalyst and were comparable to that of a free-enzyme-catalyzed reaction. The enantiomeric excess (ee) of (R)-benzoin was obtained at 99 ± 2% for the free enzyme and 96 ± 3% for the immobilized enzyme. To test the stability of the covalently immobilized enzyme, the immobilized enzyme was reused in five reaction cycles for the formation of chiral 2-hydroxypropiophenone (2-HPP) from benzaldehyde and acetaldehyde, and it retained 96% of its original activity after five reaction cycles. Chirality 27:635-642, 2015.

Zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source

The zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source and zinc as reductant was successfully conducted. The presented method provides a low-cost, environmentally friendly and practical preparation of α-aryl amino esters, α-hydroxyketones and phenylethylenes. By using D2O as deuterium source, the corresponding products were obtained in high efficiency with excellent deuterium incorporation rate, which gives a cheap and safe tool for access to valuable deuterium-labelled compounds. This journal is

Structural insights into the desymmetrization of bulky 1,2-dicarbonyls through enzymatic monoreduction

Benzil reductases are dehydrogenases preferentially active on aromatic 1,2-diketones, but the reasons for this peculiar substrate recognition have not yet been clarified. The benzil reductase (KRED1-Pglu) from the non-conventional yeast Pichia glucozyma showed excellent activity and stereoselectivity in the monoreduction of space-demanding aromatic 1,2-dicarbonyls, making this enzyme attractive as biocatalyst in organic chemistry. Structural insights into the stereoselective monoreduction of 1,2-diketones catalyzed by KRED1-Pglu were investigated starting from its 1.77 ? resolution crystal structure, followed by QM and classical calculations; this study allowed for the identification and characterization of the KRED1-Pglu reactive site. Once identified the recognition elements involved in the stereoselective desymmetrization of bulky 1,2-dicarbonyls mediated by KRED1-Pglu, a mechanism was proposed together with an in silico prediction of substrates reactivity.

Organocatalytic Synthesis of Substituted Vinylene Carbonates

The organocatalytic synthesis of substituted vinylene carbonates from benzoins and acyloins was studied using diphenyl carbonate as a carbonyl source. A range of N-Heterocyclic Carbene (NHC) precursors were screened and it was found that imidazolium salts were the most active for this transformation. The reaction occurs at 90 °C under solvent-free conditions. A wide range of substituted vinylene carbonates (symmetrical and unsymmetrical, aromatic or aliphatic), including some derived from natural products, were prepared with 20–99% isolated yields (24 examples). The reaction was also developed using thermomorphic polyethylene-supported organocatalysts as recoverable and recyclable species. The use of such species facilitates the workup and allows the synthesis of vinylene carbonates on the preparative scale (>30 g after 5 runs). (Figure presented.).