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

• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 6832-17-3 2-diazo-1-(4-methoxyphenyl)ethanone 
• 55991-65-6 [1-(4-methoxyphenyl)vinyloxy]trimethylsilane 
• 132531-87-4 2-(4-methoxyphenyl)-1-(phenylsulfenyl)-1,2-bis(trifluoroacetoxy)ethane 
• 97006-85-4 [1,2-Dihydroxy-2-(4-methoxy-phenyl)-ethyl]-phosphonic acid diethyl ester 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 74087-85-7 3,3-dimethyldioxirane 
• 171119-05-4 2-Oxo-2-(4-methoxyphenyl)ethyl formate 
• 178180-83-1 1-Methoxy-1-(p-methoxyphenyl)-oxiran 
• 51440-56-3 1-Methoxy-4-(1-methoxy-vinyl)-benzene 
• 58518-78-8 p-methoxyphenacyl acetate 
• 166248-67-5 1'-(4-methoxyphenyl)-<2'-<(1,1-dimethylethyl)dimethylsilyl>oxy>ethanol 
• 105782-42-1 (2RS,3SR)-2,3-epoxy-1-(4-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one 

Downstream Products

• 178180-80-8 2-(p-Methoxyphenyl)-propan-1,2-diol 
• 68940-85-2 2,3-dihydroxy-1-(4-methoxyphenyl)propan-1-one 
• 35512-31-3 4-(4-methoxyphenyl)-1H-imidazole 
• 37715-28-9 3-hydroxy-5,7-dimethoxy-2-(4-methoxy-phenyl)-chromenylium; chloride 
• 125219-12-7 4-(4-Methoxy-phenyl)-[1,3]dioxol-2-one 
• 155108-43-3 2,2-Diethoxy-2,5-dihydro-4(4'-methoxyphenyl)-furan 
• 21070-22-4 Methyl-phosphonic acid 2-(4-methoxy-phenyl)-2-oxo-ethyl ester 4-nitro-phenyl ester 
• 121-98-2 methyl 4-methoxybenzoate 
• 125219-02-5 C₁₈H₁₄N₂O₅ 
• 13603-63-9 (R)-1-(4-methoxyphenyl)ethane-1,2-diol 
• 100-09-4 4-methoxybenzoic acid 
• 50-00-0 formaldehyd 
• 113680-16-3 diethyl (2-(4-methoxyphenyl)-2-oxoethyl) phosphate 
• 1025955-30-9 2-methoxymethoxy-1-(4-methoxy-phenyl)-ethanone 

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.

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%).

Synthesis of pentafluorobenzene-based NHC adducts and their catalytic activity in the microwave-assisted reactions of aldehydes

N-Heterocyclic carbenes (NHCs) have been widely used in organometallic chemistry as ligands, as well as standalone organocatalysts in various reactions, mostly using aromatic aldehydes as substrates. We have previously demonstrated the efficiency of azolium-2-carboxylate zwitterions in the hydroxymethylation of aldehydes, especially aliphatic aldehydes, under microwave irradiation. In the present work, we report a series of pentafluorobenzene-based NHC adducts and their efficiency in the hydroxymethylation and self-condensation of aliphatic and aromatic aldehydes using microwave irradiation. The free carbenes are released under the reaction conditions and 1,3-dimesityl-2-(perfluorophenyl)imidazolidine and 1,3-bis(2,6-dimethylphenyl)-2-(perfluorophenyl)imidazolidine proved to be the most potent precatalysts.