586-37-8

Basic information

• Product Name: 3-Methoxyacetophenone
• Synonyms: 3-ACETYLANISOLE;3'-METHOXYACETOPHENONE;3-METHOXYACETOPHENONE;1-(3-methoxyphenyl)ethanone;M-ACETYLANISOLE;M-ACETANISOLE;3'-Methoxyacetophenone m-Acetanisole 3-Acetanisole;3-Methoxyacetophenone,>99%
• CAS NO: 586-37-8
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• EINECS: 209-573-3
• Product Categories: Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 586-37-8.mol
• Article Data: 164

Chemical Properties

• Melting Point: -7 °C
• Boiling Point: 239-241 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear slightly yellow to slightly brown/Liquid
• Density: 1.094 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.41-10.665Pa at 20-25℃
• Refractive Index: n20/D 1.542(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: Fully miscible in water. Soluble in alcohol.
• Sensitive: Light Sensitive
• BRN: 878552
• CAS DataBase Reference: 3-Methoxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxyacetophenone(586-37-8)
• EPA Substance Registry System: 3-Methoxyacetophenone(586-37-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/38-22-36/37/38
• Safety Statements: 23-24/25-37/39-26-36
• WGK Germany: 3
• Hazardous Substances Data: 586-37-8(Hazardous Substances Data)

Usage

Chemical Properties

clear slightly yellow to slightly brown liquid

Uses

It is applied in the asymmetric transfer hydrogenation of ketones catalyzed by ruthenium(II) complexes.

Synthesis Reference(s)

Journal of the American Chemical Society, 109, p. 7137, 1987 DOI: 10.1021/ja00257a038Synthesis, p. 406, 1987 DOI: 10.1055/s-1987-27965

Flammability and Explosibility

Nonflammable

Upstream product

• 141-97-9 ethyl acetoacetate 
• 1711-05-3 m-anisoyl chloride 
• 766-85-8 3-methoxy-1-iodobenzene 
• 109-92-2 ethyl vinyl ether 
• 615-37-2 ortho-methylphenyl iodide 
• 269391-96-0 1-(2-iodo-5-methoxy)-phenylethanol 
• 89691-63-4 1-(3-methoxy)-phenylethanol 
• 768-70-7 1-ethynyl-3-methoxybenzene 
• 108-24-7 acetic anhydride 
• 2398-37-0 3-methoxyphenyl bromide 
• 139214-44-1 2-(3-methoxyphenyl)-2-methyl-1,3-dithiolane 
• 66107-33-3 3-methoxyphenyl triflate 
• 99-03-6 1-(3-aminophenyl)ethanone 
• 1139857-62-7 2-hydroxy-2-(3-methoxyphenyl)propanenitrile 

Downstream Products

• 855365-08-1 1,5-bis-(3-methoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-pentane-1,5-dione 
• 22966-24-1 (E)-1-(3-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 130820-51-8 (2E)-1-(3-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 32904-95-3 4-methoxy-1-phenylbutane-1,3-dione 
• 29681-99-0 m-methoxybenzoylacetone 
• 120125-63-5 cis/trans-ethyl 2-(3-methoxyphenyl)-2-methyl-1-oxirane-1-carboxylate 
• 87116-40-3 (2E)-1,3-bis(3-methoxyphenyl)prop-2-en-1-one 
• 73873-85-5 5-[1-(3-methoxy-phenyl)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 25108-57-0 3-(1-methylethenyl)anisole 
• 33733-83-4 3-tert-butyl-1-methoxybenzene 
• 66702-77-0 1-(3-Methoxy-phenyl)-2-nitrooxy-ethanone 
• 128588-63-6 2,3-Diphenyl-5-(3-methoxyphenyl)pyrrole 
• 22966-24-1 1-(3-methoxyphenyl)-3-phenyl-2-propene-1-one 
• 80534-78-7 methyl-1 metamethoxybenzylidene cyanoacetate d'ethyle 

Relevant articles and documents

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.

Interfacially synthesized 2D COF thin film photocatalyst: efficient photocatalyst for solar formic acid production from CO2and fine chemical synthesis

The targeted synthesis of an efficient, visible light active, recyclable, freestanding covalent organic framework thin film photocatalyst for multi-faceted photocatalysis is the essence of the proposed work. A simple, scalable, reagent free synthesis of a thin film at the interface of 5,10,15,20-tetra-(4-aminophenyl)porphyrin, 2-vinylbenzene-1,4-dicarbaldehyde in nitrobenzene and aqueous glyoxal affords centimetre sized continuous 2D thin film with substantial stability, flexibility and efficient visible light activity. Strikingly different from the regular imine based COF, the incorporation of the glyoxal unit as a modulator helps in band gap tuning and induces flexibility within the thin film. An interplay between time and concentration helps in achieving a thin film photocatalyst with efficient photocatalytic activity for 1,4-NADH regeneration and selective formic acid formation from CO2. The optimum band edge position of the thin film photocatalyst also enables solar fine chemical synthesisviareductive dehalogenation under visible light illumination with excellent recyclability. The present work gives insight into visible light active thin film formation en route to metal-free sustainable photocatalysis.

o-Quinone methide with overcrowded olefin component as a dehydridation catalyst under aerobic photoirradiation conditions

Ano-quinone methide (o-QM) featuring an overcrowded olefinic framework is introduced, which exhibits dehydridation activity owing to its enhanced zwitterionic character, particularly through photoexcitation. The characteristics of thiso-QM enable the operation of dehydridative catalysis in the oxidation of benzylic secondary alcohols under aerobic photoirradiation conditions. An experimental analysis and density functional theory calculations provide mechanistic insights; the ground-state zwitterionic intermediate abstracts a hydride and proton simultaneously, and the active oxygen species facilitate catalyst regeneration.