51863-60-6

Basic information

• Product Name: 3,5-Dihydroxyacetophenone
• Synonyms: 1-(3,5-dihydroxyphenyl)-ethanone;5-ACETYLRESORCINOL;3',5'-DIHYDROXYACETOPHENONE;3,5-DIHYDROXYACETOPHENONE;3,5-DIHYDROXYACETOPHENONE MONOHYDRATE;ETHANONE, 1-(3,5-DIHYDROXYPHENYL)-;1-(3,5-dihydroxyphenyl)ethan-1-one;3,5-DIHYDROXYACETOPHENON
• CAS NO: 51863-60-6
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• EINECS: 257-480-1
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Acetophenones & Derivatives (substituted);Building Blocks for Dendrimers;Functional Materials;Alcohols;Monomers;Polymer Science
• Mol File: 51863-60-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 145-146 °C(lit.)
• Boiling Point: 234.6°C (rough estimate)
• Flash Point: 159.6 °C
• Appearance: Off-white to brown/Powder
• Density: 1.2143 (rough estimate)
• Refractive Index: 1.4447 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.63±0.10(Predicted)
• BRN: 1936502
• CAS DataBase Reference: 3,5-Dihydroxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dihydroxyacetophenone(51863-60-6)
• EPA Substance Registry System: 3,5-Dihydroxyacetophenone(51863-60-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 51863-60-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 51863-60-6 differently. You can refer to the following data:
1. 3',5'-Dihydroxyacetophenone is a dihydroxy derivative of acetophenone. 3',5'-Dihydroxyacetophenone shows inhibitory activity towards plant germination and growth as well as some antitumor activity.
2. 3'',5''-Dihydroxyacetophenone is a dihydroxy derivative of acetophenone. 3'',5''-Dihydroxyacetophenone shows inhibitory activity towards plant germination and growth as well as some antitumor activity.

Preparation

Preparation from 3,5-dimethoxyacetophenone (SM) by demethylation with aluminium chloride in refluxing chlorobenzene (71%) The starting material (SM) was prepared by a three-step procedure from 3,5-dimethoxy-benzoic acid.

Upstream product

• 90664-17-8 1-(3,5-Dibenzyloxyphenyl)-2-methylsulfonyl-1-ethanon 
• 50513-72-9 (3,5-di-benzyloxy)benzoic acid benzyl ester 
• 28924-21-2 3,5-dibenzyloxyacetophenone 
• 35086-59-0 1-(3',5'-diacetoxyphenyl)ethanone 
• 39151-19-4 1-(3,5-dimethoxyphenyl)ethan-1-one 

Downstream Products

• 63437-99-0 1-[3-Hydroxy-5-(2-hydroxy-propoxy)-phenyl]-ethanone 
• 63437-98-9 1-[3-Hydroxy-5-(3-hydroxy-propoxy)-phenyl]-ethanone 
• 162783-64-4 1-{3-[2-(2-{2-[2-(3-acetyl-5-hydroxy-phenoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-5-hydroxy-phenyl}-ethanone 
• 335274-51-6 O-acetophenone 3,5-bis(N,N'-diethylthiocarbamate) 
• 35086-59-0 1-(3',5'-diacetoxyphenyl)ethanone 
• 4299-72-3 5-ethylresorcinol 
• 406919-42-4 3',5'-diisovalerylacetophenone 
• 406919-44-6 3',5'-dipivaloyloxyacetophenone 
• 28924-21-2 3,5-dibenzyloxyacetophenone 
• 62932-92-7 2-bromo-1-(3,5-dihydroxyphenyl)ethan-1-one 
• 208930-08-9 m,m'-di(dodecyloxy)acetophenone 
• 63437-86-5 1-[3-Hydroxy-5-(2-hydroxy-ethoxy)-phenyl]-ethanone 
• 63438-00-6 1-[3-(2,3-Dihydroxy-propoxy)-5-hydroxy-phenyl]-ethanone 
• 39151-19-4 1-(3,5-dimethoxyphenyl)ethan-1-one 

Relevant articles and documents

Synthesis of (R)-bambuterol based on asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with incubated whole cells of Williopsis californica JCM 3600

To achieve the synthesis of (R)-bambuterol, a prodrug of (R)-terbutaline, asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with whole cells of Williopsis californica JCM 3600 pre-incubated on glycerol as a carbon source was examined. Initially, the insolubility of this crystalline substrate (mp 126-127 C) in the incubation broth was an obstacle that needed to be overcome. To solve the problem, the concentration of glycerol was increased to 10% during reduction. Glycerol worked well for recycling oxido-reduction cofactors and for enhancing the water solubility of the substrate. The reduction proceeded smoothly to give enantiomerically pure (R)-alcohol in 81% isolated yield.

A Practical Method for the Preparation of 2-Arylbenzofurans and the Synthesis of Moracin A and B

Oxidative rearrangement of 2-benzyloxychalcones 2 with Tl(NO3)3 in methanol to 1,2-diaryl-3,3-dimethoxy-1-propanones 3, alkaline degradation to aryl 2-benzyloxybenzyl ketones 4, debenzylation, and ring closure gave 2-arylbenzofurans 1.In this way moracin A and B (1a, b), further 2-(2,4-dihydroxyphenyl)-5,6-dimethoxybenzofuran (1c) were synthesized.The latter was not identical with a substance isolated from Myroxylon balsamum for which structure 1c was claimed.