3027-13-2

Basic information

• Product Name: 3-METHOXYPHENYLACETONE
• Synonyms: 2-Propanone, 1-(3-methoxyphenyl)-;M-METHOXYPHENYL ACETONE;3-METHOXYPHENYLACETONE;1-(3-METHOXYPHENYL)ACETONE;1-(3-Methoxyphenyl)-2-propanone;3-methoxyphenylpropan-2-one;3-METHOXYBENZYL METHYL KETONE;Methyl(3-methoxybenzyl) ketone
• CAS NO: 3027-13-2
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• EINECS: 221-191-9
• Product Categories: Aromatic Ketones (substituted);C10;Carbonyl Compounds;Ketones
• Mol File: 3027-13-2.mol
• Article Data: 29

Chemical Properties

• Melting Point: 258 °C
• Boiling Point: 258-260 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.911 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0133mmHg at 25°C
• Refractive Index: n20/D 1.5252(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Miscible with dimethyl sulfoxide.
• BRN: 2044357
• CAS DataBase Reference: 3-METHOXYPHENYLACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHOXYPHENYLACETONE(3027-13-2)
• EPA Substance Registry System: 3-METHOXYPHENYLACETONE(3027-13-2)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3027-13-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 3027-13-2 differently. You can refer to the following data:
1. 3-Methoxyphenylacetone is a substituted phenylacetone used in the preparation of optically active cyanohydrins. 3-Methoxyphenylacetone is also used in the preparation of CNS active compounds.
2. 3-Methoxyphenylacetone is employed in the preparation of optically active cyanohydrins. It is also used in the synthesis of central nervous system (CNS) active compounds. Further, it plays an important role in the preparation of 4-amino-3-methoxypropiophenone.

InChI:InChI=1/C10H12O2/c1-8(11)6-9-4-3-5-10(7-9)12-2/h3-5,7H,6H2,1-2H3

Upstream product

• 25594-66-5 1-cyano-1-(m-methoxyphenyl)propan-2-one 
• 996-82-7 sodium diethylmalonate 
• 6834-42-0 3-methoxyphenylacetic acid chloride 
• 17354-63-1 4-(2-nitro-propenyl)-anisole 
• 18738-95-9 1-(m-methoxyphenyl)-2-nitro-1-propene 
• 766-85-8 3-methoxy-1-iodobenzene 
• 128190-66-9 potassium enolate of acetone 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 100-66-3 methoxybenzene 
• 67-64-1 acetone 
• 144380-81-4 (Z)-1-(3-Methoxy-phenyl)-propen-2-ol 
• 78-95-5 chloroacetone 
• 79-24-3 Nitroethane 
• 591-31-1 3-methoxy-benzaldehyde 

Downstream Products

• 34322-78-6 3-(m-methoxyphenyl)propan-2-ol 
• 76106-55-3 1-(3-methoxyphenyl)-5,5-dimethylhex-3-en-2-one 
• 136178-70-6 2,2-dimethoxy-1-(3-methoxyphenyl)propane 
• 586-38-9 3-Methoxybenzoic acid 
• 71901-41-2 (+)-(2S)-1-(3-methoxyphenyl)propan-2-ol 
• 120869-14-9 5-(3-Methoxy-phenyl)-5-methyl-2-phenyl-4,5-dihydro-oxazole 
• 120869-02-5 N-[1-(3-Methoxy-phenyl)-2-oxo-propyl]-benzamide 
• 120869-06-9 N-[2-Hydroxy-1-(3-methoxy-phenyl)-propyl]-benzamide 
• 802904-60-5 3-(2-Methylamino-propyl)-phenol 
• 69390-44-9 (E)-N-(1-(3-methoxyphenyl)prop-1-en-2-yl)acetamide 
• 69390-44-9 (Z)-N-(1-(3-methoxyphenyl)prop-1-en-2-yl)acetamide 
• 197145-37-2 3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one 

Relevant articles and documents

Catalytic SNAr Hydroxylation and Alkoxylation of Aryl Fluorides

Nucleophilic aromatic substitution (SNAr) is a powerful strategy for incorporating a heteroatom into an aromatic ring by displacement of a leaving group with a nucleophile, but this method is limited to electron-deficient arenes. We have now established a reliable method for accessing phenols and phenyl alkyl ethers via catalytic SNAr reactions. The method is applicable to a broad array of electron-rich and neutral aryl fluorides, which are inert under classical SNAr conditions. Although the mechanism of SNAr reactions involving metal arene complexes is hypothesized to involve a stepwise pathway (addition followed by elimination), experimental data that support this hypothesis is still under exploration. Mechanistic studies and DFT calculations suggest either a stepwise or stepwise-like energy profile. Notably, we isolated a rhodium η5-cyclohexadienyl complex intermediate with an sp3-hybridized carbon bearing both a nucleophile and a leaving group.

Synthesis of Benzo[ b]furans by Intramolecular C-O Bond Formation Using Iron and Copper Catalysis

One-pot processes for the synthesis of benzo[b]furans from 1-aryl- or 1-alkylketones using nonprecious transition metal catalysts have been developed. Regioselective iron(III)-catalyzed halogenation of the aryl ring, followed by iron- or copper-catalyzed O-arylation allowed the synthesis of various structural analogues, including the benzo[b]furan-derived natural products corsifuran C, moracin F, and caleprunin B.

Nickel-Catalyzed Mono-Selective α-Arylation of Acetone with Aryl Chlorides and Phenol Derivatives

The challenging nickel-catalyzed mono-α-arylation of acetone with aryl chlorides, pivalates, and carbamates has been achieved for the first time. A nickel/Josiphos-based catalytic system is shown to feature unique catalytic behavior, allowing the highly selective formation of the desired mono-α-arylated acetone. The developed methodology was applied to a variety of (hetero)aryl chlorides including biologically relevant derivatives. The methodology has been extended to the unprecedented coupling of acetone with phenol derivatives. Mechanistic studies allowed the isolation and characterization of key Ni0 and NiII catalytic intermediates. The Josiphos ligand is shown to play a key role in the stabilization of NiII intermediates to allow a Ni0/NiII catalytic pathway. Mechanistic understanding was then leveraged to improve the protocol using an air-stable NiII pre-catalyst.