4136-21-4

Basic information

• Product Name: 2-HYDROXY-1-(4-METHOXYPHENYL)-1-ETHANONE
• Synonyms: A-HYDROXY-4-METHOXYACETOPHENONE;2-HYDROXY-1-(4-METHOXYPHENYL)-1-ETHANONE;2-HYDROXY-1-(4-METHOXYPHENYL)ETHANONE;alpha-hydroxy-4'-methoxyacetophenone;1-(4-Methoxyphenyl)-2-hydroxyethanone;4'-Methoxy-α-hydroxyacetophenone;α-Hydroxy-4'-methoxyacetophenone;NSC 67341
• CAS NO: 4136-21-4
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 223-955-7
• Mol File: 4136-21-4.mol
• Article Data: 92

Chemical Properties

• Melting Point: 100-103°C
• Boiling Point: 316.6 °C at 760 mmHg
• Flash Point: 129.4 °C
• Appearance: /
• Density: 1.166 g/cm³
• PKA: 12.88±0.10(Predicted)
• CAS DataBase Reference: 2-HYDROXY-1-(4-METHOXYPHENYL)-1-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-1-(4-METHOXYPHENYL)-1-ETHANONE(4136-21-4)
• EPA Substance Registry System: 2-HYDROXY-1-(4-METHOXYPHENYL)-1-ETHANONE(4136-21-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 4136-21-4(Hazardous Substances Data)

Usage

Preparation

Obtained by photocatalytic oxidation of 2-(4-methoxyphenyl)-1,2-ethanediol using silica-encapsulated H3PW12O40 as photocatalyst in acetonitrile for 1 h at r.t. under oxygen as the sole reoxidant of the catalyst Also obtained by treatment of 4-methoxyacetophenone with iodosobenzene in methanolic sodium hydroxide (50%).

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 3453, 1985 DOI: 10.1016/S0040-4039(00)98662-3

Upstream product

• 105782-42-1 (2RS,3SR)-2,3-epoxy-1-(4-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one 
• 67-64-1 acetone 
• 57508-48-2 carbethoxyacetamidine hydrochloride 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 40140-16-7 ethyl (p-methoxyphenyl)oxoacetate 
• 32345-64-5 1-(4-methoxyphenyl) ethane-1,2-diol 
• 64-18-6 formic acid 
• 1076-95-5 p-methoxyphenylglyoxal 
• 122-52-1 triethyl phosphite 
• 55991-65-6 [1-(4-methoxyphenyl)vinyloxy]trimethylsilane 
• 123-11-5 4-methoxy-benzaldehyde 
• 298-12-4 Glyoxilic acid 
• 67-56-1 methanol 
• 93435-57-5 α-tosyloxy-p-methoxyacetophenone 

Downstream Products

• 178180-80-8 2-(p-Methoxyphenyl)-propan-1,2-diol 
• 125219-12-7 4-(4-Methoxy-phenyl)-[1,3]dioxol-2-one 
• 113680-16-3 diethyl (2-(4-methoxyphenyl)-2-oxoethyl) phosphate 
• 427875-98-7 (2R,3R,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one 
• 427875-99-8 (2R,3S,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one 
• 131029-11-3 (R)-2-(t-butyldimethylsiloxy)-1-(4-methoxyphenyl)ethanol 
• 131029-14-6 (R)-2-hydroxy-2-(4-methoxyphenyl)ethyl acetate 
• 131029-13-5 (R)-2-(t-butyldimethylsiloxy)-1-(4-methoxyphenyl)ethyl benzoate 
• 131029-12-4 (S)-2-(t-butyldimethylsiloxy)-1-(4-methoxyphenyl)ethyl benzoate 
• 10557-27-4 1-(4-methoxy-phenyl)-propane-1,2-dione 
• 1226790-02-8 3,3-dibromo-1-(4-methoxyphenyl)prop-2-en-1-one 
• 1280492-50-3 4-(4-methoxyphenyl)-2,3-dihydro-[1,2,5]-thiadiazole-1,1-dioxide 
• 1280492-72-9 (R)-3-(4-methoxyphenyl)[1,2,5]thiadiazolidine-1,1-dioxide 

Relevant articles and documents

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).

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.

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.