5706-85-4

Basic information

• Product Name: 2-hydroxy-1-(4-hydroxyphenyl)ethanone
• Synonyms: 1-(4-Hydroxyphenyl)-2-hydroxyethanone;4-Hydroxyphenacyl alcohol;4'-Hydroxy-α-hydroxyacetophenone;α,4'-Dihydroxyacetophenone;ω,4'-Dihydroxyacetophenone;C13635
• CAS NO: 5706-85-4
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• Mol File: 5706-85-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 177–178°C
• Boiling Point: 358.8°Cat760mmHg
• Flash Point: 185°C
• Appearance: /
• Density: 1.301g/cm³
• CAS DataBase Reference: 2-hydroxy-1-(4-hydroxyphenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-1-(4-hydroxyphenyl)ethanone(5706-85-4)
• EPA Substance Registry System: 2-hydroxy-1-(4-hydroxyphenyl)ethanone(5706-85-4)

Safety Data

• Hazardous Substances Data: 5706-85-4(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of p-hydroxy-a-bromoacetophenone with formic acid in the presence of DBU,in benzene at 0°, followed by saponification of the intermediate formate ester with sodium hydroxide in methanol (99%) in methylene chloride, with the same treatment (49%).

Upstream product

• 194027-03-7 (S)-2-((S)-2-Amino-propionylamino)-propionic acid 2-(4-hydroxy-phenyl)-2-oxo-ethyl ester 
• 20816-46-0 α,α-dimethyl-p-hydroxyphenacyl acetate 
• 50-00-0 formaldehyd 
• 123-08-0 4-hydroxy-benzaldehyde 
• 6305-04-0 p-hydroxyphenacyl chloride 
• 2491-38-5 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone 
• 99-93-4 4-Hydroxyacetophenone 
• 270090-90-9 N-Boc-O-(4-hydroxyphenacyl)-Ala-Ala 
• 2380-75-8 1-(4-hydroxyphenyl)-1,2-ethanediol 
• 82246-94-4 4-(1-Hydroxy-2-phenoxy-ethyl)-phenol 
• 41978-29-4 ω-Phenoxy-p-hydroxy-acetophenon 
• 123-07-9 4-Ethylphenol 
• 2628-17-3 4-Vinylphenol 
• 99233-31-5 1-(4-hydroxyphenyl)-2-iodoethanone 

Downstream Products

• 23445-35-4 5-β-D-glucopyranosyloxy-3,7-dihydroxy-2-(4-hydroxy-phenyl)-chromenylium; chloride 
• 109649-54-9 (4-hydroxy-phenyl)-glyoxal-bis-phenylhydrazone 
• 479400-63-0 2-hydroxy-1-[4-(3-methyl-but-2-enyloxy)-phenyl]-ethanone 
• 125107-92-8 pelargonidin-3-O-glucoside 
• 84002-48-2 (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 
• 132020-70-3 7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one 
• 29682-12-0 1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone 
• 64-18-6 formic acid 
• 99-96-7 4-hydroxy-benzoic acid 
• 42528-99-4 2,4’-diacetoxyacetophenone 

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.

Selective oxidation of aliphatic C-H bonds in alkylphenols by a chemomimetic biocatalytic system

Selective oxidation of aliphatic C-H bonds in alkylphenols serves significant roles not only in generation of functionalized intermediates that can be used to synthesize diverse downstream chemical products, but also in biological degradation of these environmentally hazardous compounds. Chemo-, regio-, and stereoselectivity; controllability; and environmental impact represent the major challenges for chemical oxidation of alkylphenols. Here, we report the development of a unique chemomimetic biocatalytic system originated from the Gram-positive bacterium Corynebacterium glutamicum. The system consisting of CreHI (for installation of a phosphate directing/ anchoring group), CreJEF/CreG/CreC (for oxidation of alkylphenols), and CreD (for directing/anchoring group offloading) is able to selectively oxidize the aliphatic C-H bonds of p-And m-Alkylated phenols in a controllable manner. Moreover, the crystal structures of the central P450 biocatalyst CreJ in complex with two representative substrates provide significant structural insights into its substrate flexibility and reaction selectivity.

Substituted phenacyl molecules and photoresponsive polymers

Substituted phenacyl molecules are provided and employed to create molecules and polymers/copolymers that exhibit photoresponsiveness. In some instances, the substituted phenacyl molecule is incorporated into the polymer/copolymer backbone, and photoirradiation of the polymer/copolymer causes the substituted phenacyl group to break down and the polymer/copolymer to undergo degradation. In other instances, the substituted phenacyl molecules extend as a side chain from the polymer/copolymer backbone. In yet other instances the substituted phenacyl molecules extend as a side chain from the polymer/copolymer backbone, and a drug or polymer additive is linked to the photoresponsive substituted phenacyl group such that photoirradiation releases the drug or additive. In yet other embodiments the substituted phenacyl molecules extend as a side chain from the polymer/copolymer backbone, and serve to link the polymer/copolymer to another polymer/copolymer backbone, and photoirradiation breaks the links.