1835-11-6

Basic information

• Product Name: 4-BENZYLOXY-3-METHOXYACETOPHENONE
• Synonyms: TIMTEC-BB SBB008382;1-(3-methoxy-4-(phenylmethoxy)phenyl)ethanone;4’-(benzyloxy)-3’-methoxy-acetophenon;Acetophenone, 4'-(benzyloxy)-3'-methoxy-;Ethanone, 1-(3-methoxy-4-(phenylmethoxy)phenyl)-;1-[4-(BENZYLOXY)-3-METHOXYPHENYL]ETHANONE;4'-BENZYLOXY-3'-METHOXYACETOPHENONE;4-BENZYLOXY-3-METHOXYACETOPHENONE
• CAS NO: 1835-11-6
• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.3
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Aromatics;Intermediates
• Mol File: 1835-11-6.mol

Chemical Properties

• Melting Point: 85-87°C
• Boiling Point: 396.5 °C at 760 mmHg
• Flash Point: 185.2 °C
• Appearance: /
• Density: 1.115g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetonitrile (Slightly), Dichloromethane (Slightly), DMSO (Slightly, Heated)
• BRN: 1885776
• CAS DataBase Reference: 4-BENZYLOXY-3-METHOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXY-3-METHOXYACETOPHENONE(1835-11-6)
• EPA Substance Registry System: 4-BENZYLOXY-3-METHOXYACETOPHENONE(1835-11-6)

Safety Data

• Safety Statements: 22-24/25
• RTECS: AM5966000
• Hazardous Substances Data: 1835-11-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-BENZYLOXY-3-METHOXYACETOPHENONE is used as an intermediate in the synthesis of Epinephrine metabolites, which are essential for the development of medications targeting various medical conditions. Its role in the production of these metabolites highlights its importance in the pharmaceutical industry.
Used in Chemical Research:
As an organic compound with distinct chemical properties, 4-BENZYLOXY-3-METHOXYACETOPHENONE is also utilized in chemical research for the exploration of new synthetic pathways and the development of novel compounds with potential applications in various fields.
Used in Analytical Chemistry:
The pale yellow solid nature of 4-BENZYLOXY-3-METHOXYACETOPHENONE makes it suitable for use in analytical chemistry, where it can be employed as a reference material or in the development of analytical methods for the detection and quantification of related compounds.

Upstream product

• 186581-53-3 diazomethane 
• 21092-94-4 3'-hydroxy4'-benzyloxyacetophenone 
• 100-44-7 benzyl chloride 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 78178-58-2 4-benzyloxy-3-methoxybenzoylacetic acid 
• 1835-12-7 3-methoxy-4-benzyloxy-α-bromoacetophenone 
• 22317-29-9 1-(4-(benzyloxy)-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 60525-32-8 ethyl 3-[4-(benzyloxy)-3-methoxyphenyl]-3-oxopropanoate 
• 1197-09-7 1-(3,4-dihydroxyphenyl)ethan-1-one 
• 77-78-1 dimethyl sulfate 
• 90-05-1 2-methoxy-phenol 
• 906668-05-1 2-(2,6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)ethan-1-one 
• 52041-27-7 1-(3'-methoxy-4'-(1-phenyl)methoxyphenyl)-2-(2'',6''-dimethoxyphenoxy)ethanal 

Downstream Products

• 2480-86-6 Apocynol 
• 1835-12-7 3-methoxy-4-benzyloxy-α-bromoacetophenone 
• 110030-28-9 4-sec-Butyl-2-methoxy-phenol 
• 16209-54-4 methyl 4-benzyloxy-3-methoxyphenylethanoate 
• 76246-82-7 3-(4-benzyloxy-3,5-dimethoxyphenyl)-1-(4-benzyloxy-3-methoxyphenyl)-2-propene-1-one 
• 119384-65-5 1-(4-benzyloxy-3-methoxyphenyl)-3-(2,3-dibenzyloxy-5-dimethoxymethylphenyl)-2-propen-1-one 
• 144735-53-5 β-(3-methoxy-4-(benzyloxy)phenyl)-β-chloracrolein 
• 75665-88-2 1-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)ethanone 
• 74613-55-1 α-methyl-4-benzyloxy-3-methoxybenzyl alcohol 
• 156482-49-4 methyl 3-(4-(benzyloxy)-3-methoxyphenyl)-3-oxopropanoate 
• 137886-47-6 2-(4-(benzyloxy)-3-methoxyphenyl)oxirane 
• 902526-01-6 (S)-1-(4-(benzyloxy)-3-methoxyphenyl)ethanol 
• 902525-97-7 2-chloro-1-(4-(benzyloxy)-3-methoxyphenyl)ethanol 
• 902525-96-6 2-bromo-1-(4-(benzyloxy)-3-methoxyphenyl)ethanol 

Relevant articles and documents

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We describe the synthesis and NMR spectroscopic analysis of three artificial lignin polymers containing only the β-O-4 substructure: syringyl-type homopolymer, p-hydroxyphenyl-type homopolymer and guaiacyl/syringyl-type heteropolymer. Using gel permeation chromatography, the weight-average degree of polymerization (DPw) of the three polymers was determined as 19.2, 38.6, and 13.9, respectively. The polymers were prepared based on the synthetic methodology of guaiacyl-type homopolymer, and were fully characterized using 1H-, 13C-, and 1H- 13C NMR spectroscopy of the acetylated and non-acetylated forms. The spectra of guaiacyl/syringyl-type heteropolymers were in good agreement with those of the β-O-4 substructure of milled wood lignin obtained from the hardwood of Japanese white birch. The Royal Society of Chemistry.

Compositional analysis of organosolv poplar lignin by using high-performance liquid chromatography/high-resolution multi-stage tandem mass spectrometry

Organosolv treatment is an efficient and environmentally friendly process to degrade lignin into small compounds. The capability of characterizing the individual compounds in the complex mixtures formed upon organosolv treatment is essential for the optimization of the further lignin conversion processes and for the rational genetic engineering of plants used to produce lignin in order to improve lignin properties. In this study, an organosolv poplar lignin sample was initially analyzed by high-resolution mass spectrometry coupled with negative-ion mode electrospray ionization ((?)ESI HRMS). Lignin monomers and dimers were found to constitute the majority of the compounds in the organosolv lignin sample. Larger lignin oligomers, such as trimers and tetramers, and some not lignin-related compounds, were also detected. A high-performance liquid chromatograph/linear quadrupole ion trap/orbitrap mass spectrometer capable of multi-stage high-resolution tandem mass spectrometry experiments (HRMSn), equipped with an (?)ESI source (HPLC/(?)ESI HRMSn), was employed to separate the unknown compounds in the organosolv mixture and to obtain structural information for the deprotonated compoundsviacollision-activated dissociation (CAD) HRMSnexperiments. To improve the understanding of the CAD behavior of deprotonated lignin-related compounds, 16 deprotonated model compounds with different functionalities and linkage types were examined. This approach enabled the assignment of likely structures for several lignin monomers, dimers, trimers, and tetramers, and some not lignin-related compounds, most likely fatty acids. Based on the proposed structures, compounds in the organosolv lignin sample contain β-O-4, 5-5, β-5, and possibly also 4-O-5 linkages. Most compounds contain G- and S-monomeric units although a small amount of H-units were also detected.

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Thio-assisted reductive electrolytic cleavage of lignin β-O-4 models and authentic lignin

Avoiding the use of expensive catalysts and harsh conditions such as elevated temperatures and high pressures is a critical goal in lignin depolymerization and valorization. In this study, we present a thio-assisted electrocatalytic reductive approach using inexpensive reticulated vitreous carbon (RVC) as the working cathode to cleave the β-O-4-type linkages in keto aryl ethers. In the presence of a pre-electrolyzed disulfide (2,2′-dithiodiethanol) and a radical inhibitor (BHT) at room temperature at a current density of 2.5 mA cm-2, cathodic reduction of nonphenolic β-O-4 dimers afforded over 90% of the corresponding monomeric C-O cleavage products in only 1.5 h. Extended to DDQ-oxidized poplar lignin, this combination of electric current and disulfide, applied over 6 h, released 36 wt% of ethyl acetate soluble fragments and 26 wt% of aqueous soluble fragments, leaving only 38 wt% of insoluble residue. These findings represent a significant improvement over the current alone values (24 wt% ethyl acetate soluble; 22 wt% aqueous soluble; 54 wt% insoluble residue) and represent an important next step in our efforts to develop a mild electrochemical method for reductive lignin deconstruction.

Iron-Catalyzed Wacker-type Oxidation of Olefins at Room Temperature with 1,3-Diketones or Neocuproine as Ligands**

Herein, we describe a convenient and general method for the oxidation of olefins to ketones using either tris(dibenzoylmethanato)iron(III) [Fe(dbm)3] or a combination of iron(II) chloride and neocuproine (2,9-dimethyl-1,10-phenanthroline) as catalysts and phenylsilane (PhSiH3) as additive. All reactions proceed efficiently at room temperature using air as sole oxidant. This transformation has been applied to a variety of substrates, is operationally simple, proceeds under mild reaction conditions, and shows a high functional-group tolerance. The ketones are formed smoothly in up to 97 % yield and with 100 % regioselectivity, while the corresponding alcohols were observed as by-products. Labeling experiments showed that an incorporated hydrogen atom originates from the phenylsilane. The oxygen atom of the ketone as well as of the alcohol derives from the ambient atmosphere.

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A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.

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