224321-19-1

Basic information

• Product Name: 2-HYDROXY-2'-METHOXYACETOPHENONE
• Synonyms: 2-HYDROXY-1-(2-METHOXYPHENYL)ETHANONE;2-HYDROXY-2'-METHOXYACETOPHENONE
• CAS NO: 224321-19-1
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• Mol File: 224321-19-1.mol

Chemical Properties

• Boiling Point: 286.8°C at 760 mmHg
• Flash Point: 114.9°C
• Appearance: /
• Density: 1.166g/cm³
• Vapor Pressure: 0.00121mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: 2-HYDROXY-2'-METHOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-2'-METHOXYACETOPHENONE(224321-19-1)
• EPA Substance Registry System: 2-HYDROXY-2'-METHOXYACETOPHENONE(224321-19-1)

Safety Data

• Hazardous Substances Data: 224321-19-1(Hazardous Substances Data)

Usage

Uses

Used in Cosmetic Industry:
2-Hydroxy-2'-Methoxyacetophenone is used as a fragrance ingredient for its pleasant and floral scent, enhancing the sensory experience of various cosmetic and personal care products such as perfumes, lotions, and soaps.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-Hydroxy-2'-Methoxyacetophenone is utilized as a preservative due to its antimicrobial properties, helping to maintain the stability and safety of formulations by preventing microbial contamination.
Used in Chemical Industry:
2-Hydroxy-2'-Methoxyacetophenone is employed as a raw material or intermediate in the synthesis of other organic compounds, contributing to the development of new chemical products and processes.
Used in Antimicrobial Applications:
2-Hydroxy-2'-Methoxyacetophenone is used as an antimicrobial agent for its ability to inhibit the growth of microorganisms, making it suitable for use in sanitizing products and as a preservative in various formulations.
Used in Anti-Inflammatory and Antioxidant Applications:
2-HYDROXY-2'-METHOXYACETOPHENONE has been studied for its potential anti-inflammatory and antioxidant properties, suggesting its use in formulations aimed at reducing inflammation and oxidative stress, thereby promoting health and well-being.

InChI:InChI=1/C9H10O3/c1-12-9-5-3-2-4-7(9)8(11)6-10/h2-5,10H,6H2,1H3

Upstream product

• 1121543-12-1 α,α-dibromo-2'-methoxyacetophenone 
• 135-02-4 ortho-anisaldehyde 
• 298-12-4 Glyoxilic acid 
• 67-56-1 methanol 
• 135339-88-7 ((1-(2-methoxyphenyl)vinyl)oxy)trimethylsilane 
• 50-00-0 formaldehyd 
• 6706-96-3 2,2'-dimethoxybenzoin 
• 579-74-8 2-Methoxyacetophenone 
• 31949-21-0 bromomethyl 2-methoxyphenyl ketone 

Downstream Products

• 393796-18-4 (3S)-3-[(R)-(o-anisoyl)hydroxymethyl]-1-indanone 
• 346666-21-5 (2R,3R)-2,3-Dihydroxy-1-(2-methoxy-phenyl)-nonan-1-one 
• 346666-03-3 (2R,3S)-2,3-Dihydroxy-1-(2-methoxy-phenyl)-nonan-1-one 
• 346666-25-9 (2R,3R)-4-Benzyloxy-2,3-dihydroxy-1-(2-methoxy-phenyl)-butan-1-one 
• 346666-07-7 (2R,3S)-4-Benzyloxy-2,3-dihydroxy-1-(2-methoxy-phenyl)-butan-1-one 
• 346666-09-9 (2R,3S)-4-Ethyl-2,3-dihydroxy-1-(2-methoxy-phenyl)-hexan-1-one 

Relevant articles and documents

One-Pot Enzymatic-Chemical Cascade Route for Synthesizing Aromatic α-Hydroxy Ketones

2-Hydroxyacetophenone (2-HAP) is an important building block for the production of a series of natural products and pharmaceuticals; however, there is no safe, efficient, and economical method for 2-HAP synthesis. Here, a one-pot enzymatic-chemical cascade route was designed for synthesizing 2-HAP based on retrosynthetic analysis. First, a spontaneous proton-transfer reaction was designed using a computational simulation that enabled 2-HAP synthesis from the isomer 2-hydroxy-2-phenylacetaldehyde. A route for 2-hydroxy-2-phenylacetaldehyde synthesis was then constructed by introducing the unnatural substrate glyoxylic acid into a C-C ligation reaction catalyzed by Candida tropicalis pyruvate decarboxylase. Assembly and optimization of this enzymatic-chemical cascade route resulted in a final yield of 92.7%. Furthermore, stereospecific carbonyl reductases were introduced to construct a synthetic application platform that enabled further transformation of 2-HAP into (S)- and (R)-1-phenyl-1,2-ethanediol. This method of cascading spontaneous chemical and enzymatic reactions to synthesize chemicals offers insight into avenues for synthesizing other valuable chemicals.

Chiral Bidentate Phosphoramidite-Pd Catalyzed Asymmetric Decarboxylative Dipolar Cycloaddition for Multistereogenic Tetrahydrofurans with Cyclic N-Sulfonyl Ketimine Moieties

An asymmetric [3 + 2] cycloaddition of vinyl ethylenecarbonates (VECs) and (E)-3-arylvinyl substituted benzo[d] isothiazole 1,1-dioxides has been developed using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst, providing a wide variety of chiral multistereogenic vinyltetrahydrofurans in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).

Palladium-Catalyzed (3+3) Annulation of Allenylethylene Carbonates with Nitrile Oxides

In this paper, we designed and synthesized a new type of cyclic carbonates, allenylethylene carbonates (AECs). With AECs as reactive precursors, we developed palladium-catalyzed (3+3) annulation of AECs with nitrile oxides. Various AECs worked well in this reaction under mild reaction conditions. A variety of 5,6-dihydro-1,4,2-dioxazine derivatives with allenyl quaternary stereocenters can be accessed in a facile manner in high yields (≤98%).

Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes

A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.

NON-IONIC ARYL KETONE BASED POLYMERIC PHOTO-ACID GENERATORS

Non-ionic photo-acid generating (PAG) polymerizable monomers were prepared that contain a side chain sulfonate ester of an alpha-hydroxy aryl ketone. The aryl ketone group has a perfluorinated substituent alpha to the ketone carbonyl. The sulfur of the sulfonate ester is also directly linked to a fluorinated group. PAG polymers prepared from the PAG monomers release a strong sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development.

NON-IONIC LOW DIFFUSING PHOTO-ACID GENERATORS

Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group. The disclosed non-polymeric PAGs release a strong sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs undergo a thermal reaction to form a sulfonic acid.

Divergent synthesis of N-heterocycles by Pd-catalyzed controllable cyclization of vinylethylene carbonates

Here, we report a palladium-catalyzed controllable cyclization of vinyl ethylene carbonates that proceeds through formal migration [2+3] and [5+2] cycloadditions, respectively, under mild conditions. The transformation described here affords a series of synthetically versatile 5,7-membered N-heterocycles which are found in natural products and pharmaceuticals with biological and medicinal properties.

Enantioselective [3 + 2] Cycloaddition Reaction of Ethynylethylene Carbonates with Malononitrile Enabled by Organo/Metal Cooperative Catalysis

The first catalytic asymmetric decarboxylative [3 + 2] cycloaddition reaction of ethynylethylene carbonates with malononitrile has been developed successfully by an organo/copper cooperative system. This strategy led to a series of optically active polysu

Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C?N/C?S Bond Formation in Allylic Surrogates

Switchable catalytic transformation of reactants can be a powerful approach towards diversity-orientated synthesis from easily available molecular synthons. Herein, an endogenous ligand-controlled, Pd-catalyzed allylic substitution allowing for either selective C?N or C?S bond formation using vinylethylene carbonates (VECs) and N-sulfonylhydrazones as coupling partners has been developed. This versatile methodology provides a facile, divergent route for the highly chemo- and stereoselective synthesis of functional allylic sulfones or sulfonohydrazides. The newly developed protocol features wide substrate scope (nearly 80 examples), broad functional group tolerance, and potential for the late-stage functionalization of bioactive compounds. The isolation and crystallographic analysis of a catalytically competent π-allyl Pd complex suggests that the pathway leading to the allylic products proceeds through a different manifold as previously proposed for the functionalization of VECs with nucleophiles.

Palladium-Catalyzed (Z)-Selective Allylation of Nitroalkanes: Access to Highly Functionalized Homoallylic Scaffolds

Nitroalkanes undergo decarboxylative allylation in the presence of vinyl-substituted cyclic carbonates, providing a wide variety of functionalized homoallylated compounds with exquisite stereocontrol. This Pd-mediated procedure features operational simplicity, versatile substrate combinations, and also allows for the sequential introduction of different allyl groups in the nitroalkane scaffolds with high levels of stereocontrol through the intermediacy of a (Z)-configured palladacyclic intermediate. As far as we know, the developed protocol is the first general Pd-mediated methodology toward (Z)-configured homoallylic nitroalkanes with attractive functional group diversity.