37951-49-8

Basic information

• Product Name: 3'-methoxypropiophenone
• Synonyms: 1-(3-methoxy-phenyl)propan-1-one;1-(3-Methoxyphenyl)-1-propanone
• CAS NO: 37951-49-8
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20108
• EINECS: 253-729-3
• Mol File: 37951-49-8.mol

Chemical Properties

• Boiling Point: 259℃
• Flash Point: 98.9 °C
• Appearance: /
• Density: 1.0812
• Refractive Index: 1.5230 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3'-methoxypropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-methoxypropiophenone(37951-49-8)
• EPA Substance Registry System: 3'-methoxypropiophenone(37951-49-8)

Safety Data

• Hazardous Substances Data: 37951-49-8(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of ethylmagnesium bromide,with m-methoxybenzonitrile (m.p. 60°)with 3-methoxybenzaldehyde and oxidation of the resulting 1-(3-methoxyphenyl)-1-propanol with sodium dichromate in sulfuric acid (70%).

Upstream product

• 1527-89-5 3-methoxybenzonitrile 
• 925-90-6 ethylmagnesium bromide 
• 52956-27-1 1-(3-methoxyphenyl)propanol 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 123-62-6 propionic acid anhydride 
• 77-78-1 dimethyl sulfate 
• 1711-05-3 m-anisoyl chloride 
• 591-31-1 3-methoxy-benzaldehyde 
• 2398-37-0 3-methoxyphenyl bromide 
• 152121-82-9 N,3‐dimethoxy‐N‐methylbenzamide 
• 58824-50-3 1-(3-methoxyphenyl)-2-propen-1-ol 
• 586-38-9 3-Methoxybenzoic acid 
• 13103-80-5 1-(3-hydroxyphenyl)propan-1-one 
• 74-88-4 methyl iodide 

Downstream Products

• 7116-39-4 3-(3-methoxyphenyl)propanoic acid ethyl ester 
• 139008-18-7 1-(m-methoxyphenyl)-1-pentadeuterophenylpropanol 
• 13103-80-5 1-(3-hydroxyphenyl)propan-1-one 
• 76473-06-8 trans-3,3'-dimethoxy-α,β-diethylstilbene 
• 76473-05-7 C₂₀H₂₄O₂ 
• 83456-27-3 3,4-Bis(3-methoxyphenyl)-3,4-hexanediol 
• 519050-99-8 [1-(3-Methoxy-phenyl)-prop-(Z)-ylidene]-hydrazine 
• 111222-52-7 N-1-(3-methoxyphenyl)propylformamide 
• 86051-92-5 methyl 4-methyl 5-oxo 5(3'methoxy)phenyl pentanoate 
• 160388-15-8 2-chloro-1-(3-methoxyphenyl)propan-1-one 
• 62103-69-9 3-propylanisole 
• 37951-53-4 3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one hydrochloride 
• 197145-37-2 3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one 
• 5959-71-7 MetaDES 

Relevant articles and documents

Chiral Primary Amine Catalyzed Enantioselective Tandem Reactions Based on Heyns Rearrangement: Synthesis of α-Tertiary Amino Ketones

Herein, we disclose a new catalytic asymmetric tandem reaction based on the Heyns rearrangement for the synthesis of chiral α-amino ketones with readily available substrates. The rearrangement is different from the Heyns rearrangement in that the α-amino ketones were obtained without the shift of the carbonyl group. The key to success is using chiral primary amine as a catalyst by mimicking glucosamine-6-phosphate synthase in catalyzing the efficient Heyns rearrangement in organisms.

Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water

Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.

Copper-catalyzed method for preparing aldehyde or ketone compound by oxidizing alcohol with oxygen as oxidizing agent and application

The invention discloses a copper-catalyzed method for preparing an aldehyde or ketone compound by oxidizing alcohol with oxygen as an oxidizing agent. Reaction is performed in an organic solvent for 4-48 hours at room temperature by using copper salt and nitroxide free radicals as catalysts and oxygen or air as an oxidizing agent to efficiently oxidize an alcohol compound into the corresponding aldehyde or ketone compound. The method is simple to operate, free of chlorides corrosive to equipment, available in raw materials and reagents, mild in reaction conditions, wide in substrate universality, good in functional group compatibility, convenient in separation and purification, environmentally friendly in the whole process and free of pollution, and is a method suitable for industrial production.

Metal-Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones

The acylation of aryl halides to prepare aryl ketones without metal catalyst represents an important yet challenging topic towards more sustainable ketone synthesis. Herein, we describe a simple and efficient metal-free protocol for the acylation of aryl halides with diketone under the irradiation of light utilizing N-methylpiperidine as base under an air atmosphere. This reaction can tolerate a wide range of functional groups and the corresponding ketones can be obtained in modest to good yields.

Isomerization of Allylic Alcohols to Ketones Catalyzed by Well-Defined Iron PNP Pincer Catalysts

[Fe(PNP)(CO)HCl] (PNP=di-(2-diisopropylphosphanyl-ethyl)amine), activated in situ with KOtBu, is a highly active catalyst for the isomerization of allylic alcohols to ketones without an external hydrogen supply. High reaction rates were obtained at 80 °C, but the catalyst is also sufficiently active at room temperature with most substrates. The reaction follows a self-hydrogen-borrowing mechanism, as verified by DFT calculations. An alternative isomerization through alkene insertion and β-hydride elimination could be excluded on the basis of a much higher barrier. In alcoholic solvents, the ketone product is further reduced to the saturated alcohol.

KOtBu-Mediated Domino Isomerization and Functionalization of Aromatic Allylic Alcohols

Transition-metal- as well as ligand-free base-mediated domino isomerization and alkylation of allylic alcohols is presented. This protocol features the conversion of simple allylic alcohols into the corresponding ketones through isomerization in the presence of a simple base. Significantly, these in situ generated ketones subsequently undergo alkylation with styrenes as electrophiles, in a domino one-pot fashion, as an atom- and step-economical chemical process.

Synthesis method for 3-methoxypropiophenone

The invention discloses a synthesis method for 3-methoxypropiophenone. The synthesis method comprises the steps of enabling magnesium and m-bromoanisole to produce a Grignard reagent in a tetrahydrofuran (THF) solution under the catalytic action of aluminum chloride, and then, subjecting the Grignard reagent to a reaction with propionitrile, thereby producing the 3-methoxypropiophenone. According to the synthesis method, the operation is simple, the process is advanced, the solvent can be recycled, and thus, the industrial production is facilitated. According to the 3-methoxypropiophenone prepared by the synthesis method, the yield reaches 88.6%, and the liquid-phase purity reaches up to 99.44% or more.

Targeting Cancer with PCPA-Drug Conjugates: LSD1 Inhibition-Triggered Release of 4-Hydroxytamoxifen

Targeting cancer with small molecule prodrugs should help overcome problems associated with conventional cancer-targeting methods. Herein, we focused on lysine-specific demethylase 1 (LSD1) to trigger the controlled release of anticancer drugs in cancer cells, where LSD1 is highly expressed. Conjugates of the LSD1 inhibitor trans-2-phenylcyclopropylamine (PCPA) were used as novel prodrugs to selectively release anticancer drugs by LSD1 inhibition. As PCPA-drug conjugate (PDC) prototypes, we designed PCPA-tamoxifen conjugates 1 a and 1 b, which released 4-hydroxytamoxifen in the presence of LSD1 in vitro. Furthermore, 1 a and 1 b inhibited the growth of breast cancer cells by the simultaneous inhibition of LSD1 and the estrogen receptor without exhibiting cytotoxicity toward normal cells. These results demonstrate that PDCs provide a useful prodrug method that may facilitate the selective release of drugs in cancer cells.

TETRAZOLINONE COMPOUND AND USE THEREOF

A tetrazolinone compound represented by formula (1): wherein R1 and R2 each represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl group; R3 represents a C1-C3 alkyl group optionally having one or more halogen atoms; R4, R5, and R6 each represents a hydrogen atom or a halogen atom; R7 represents a C1-C3 alkyl group; Q represents a divalent group selected from Group P4; and A represents a C7-C18 aralkyloxy group optionally having one or more atoms or groups selected from Group P3, has excellent control activity against pests.

Rhodium-catalyzed ketone methylation using methanol under mild conditions: Formation of α-branched products

The rhodium-catalyzed methylation of ketones has been accomplished using methanol as the methylating agent and the hydrogen-borrowing method. The sequence is notable for the relatively low temperatures that are required and for the ability of the reaction system to form α-branched products with ease. Doubly alkylated ketones can be prepared from methyl ketones and two different alcohols by using a sequential one-pot iridium- and rhodium-catalyzed process. Uniquely effective for making branched alkyl products from ketones (see scheme): The scope of the presented reaction includes aromatic and aliphatic ketones and consecutive one-pot double alkylation reactions to provide a convenient route to branched ketones from simple methyl ketones. A brief study into the mechanism of the reaction has given evidence for an aldol-based reaction pathway.