1835-14-9

Basic information

• Product Name: 4'-Hydroxy-3'-methoxypropiophenone
• Synonyms: 3-METHOXY-4-HYDROXYPROPIOPHENONE;4-HYDROXY-3-METHOXYPROPIOPHENONE;1-(4-hydroxy-3-methoxyphenyl)-1-propanone;1-(4-HYDROXY-3-METHOXY-PHENYL)-PROPAN-1-ONE;PROPIOVANILLONE;1-(4-Hydroxy-3-methoxyphenyl)-1-propanone (propiovanillone);Propioguaiacone;Propiophenone, 4'-hydroxy-3'-methoxy
• CAS NO: 1835-14-9
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• Product Categories: Aromatic Propiophenones (substituted)
• Mol File: 1835-14-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 61-62 °C
• Boiling Point: 320.716 °C at 760 mmHg
• Flash Point: 126.89 °C
• Appearance: /
• Density: 1.127 g/cm³
• Vapor Pressure: 0.000166mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.92±0.31(Predicted)
• CAS DataBase Reference: 4'-Hydroxy-3'-methoxypropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Hydroxy-3'-methoxypropiophenone(1835-14-9)
• EPA Substance Registry System: 4'-Hydroxy-3'-methoxypropiophenone(1835-14-9)

Safety Data

• Hazard Codes: T,N
• Statements: 25-51/53
• Safety Statements: 45-61
• Hazardous Substances Data: 1835-14-9(Hazardous Substances Data)

Usage

Uses

1-(4-Hydroxy-3-methoxyphenyl)-1-propanone is a derivative of Guaiacol, a precursor to various flavorants, such as eugenol and vanillin.

Preparation

Preparation by Fries rearrangement of 2-methoxyphenyl propionate, (b.p.20 140–143°)with aluminium chloride in nitrobenzene, first at 60–80° for 1 h, then at r.t. overnight, at 60° for 1 h or at 50° for 5 h (44%) ;with aluminium chloride (2 mol) in nitromethane at r.t. for 24 h (65%)with aluminium chloride in carbon disulfidewith titanium tetrachloride (2 mol) in nitromethane at r.t. for 24 h (62%)with stannic chloride (2 mol) in nitromethane at r.t. for 24 h (69%)with antimony pentachloride (2 mol) in nitromethane at r.t. for 24 h (28%) with formation of important tars.

Synthesis Reference(s)

The Journal of Organic Chemistry, 15, p. 227, 1950 DOI: 10.1021/jo01148a001

InChI:InChI=1/C10H12O3/c1-3-8(11)7-4-5-9(12)10(6-7)13-2/h4-6,12H,3H2,1-2H3

Upstream product

• 91-16-7 1,2-dimethoxybenzene 
• 79-03-8 propionyl chloride 
• 2785-87-7 2-methoxy-4-n-propylphenol 
• 90-05-1 2-methoxy-phenol 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 
• 7451-98-1 3',4'-dihydroxypropiophenone 
• 74-88-4 methyl iodide 
• 881-68-5 vanillin acetate 
• 41753-49-5 Lepidophoron 
• 802294-64-0 propionic acid 
• 6997-34-8 1-(4-hydroxy-3-methoxyphenyl)propan-1-ol 
• 7598-60-9 2-methoxyphenyl propionate 

Downstream Products

• 1087-06-5 Meprophendiol 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 144-62-7 oxalic acid 
• 121-33-5 vanillin 
• 22637-50-9 (2-Methoxy-4-propionyl-phenoxy)-acetic acid 
• 1447024-82-9 C₁₃H₁₄O₅ 
• 1678-92-8 propylcyclohexane 
• 1123-86-0 cyclohexyl ethyl ketone 
• 68505-86-2 α-Chlorpropioguajacon 
• 938070-70-3 2-(methyloxy)4-propanoylphenyl trifluoromethanesulfonate 

Relevant articles and documents

Non-plasmonic Ni nanoparticles catalyzed visible light selective hydrogenolysis of aryl ethers in lignin under mild conditions

Light-driven catalysis on catalytically versatile group VIII metals, which has been widely used in thermal catalysis, holds great potential in solar-to-chemical conversion. We report a novel photocatalysis process for the selective hydrogenolysis of aryl ethers in lignin on a heterogeneous catalyst of non-precious Ni nanoparticles supported on ZrO2. Three aryl ether bonds in lignin were successfully cleaved under mild conditions with excellent conversion and good to excellent selectivity under visible light irradiation. We also used solar irradiation to demonstrate a significant reduction in the total energy consumption. The light irradiation excited interband transitions in Ni nanoparticles and the resultant energetic electrons enhanced the activity of reductive cleavage of the aryl ethers. Its application potential was illustrated by the depolymerization of dealkaline lignin to give a total monomer yield of 9.84 wt% with vanillin, guaiacol, and apocynin as the three major products.

A convenient synthetic approach to dioncoquinone B and related compounds

A total synthesis of dioncoquinone B and related compounds, including ancistroquinones B, C and malvon A, is presented. The strategy is based on available reagents and can be used as a preparative synthesis of a number of natural and synthetic biologically active (3-alkyl)-2,7,8-di(tri)methoxy(hydroxy)-1,4-naphthoquinones.