5803-30-5

Basic information

• Product Name: 2,5-DIMETHOXYPROPIOPHENONE
• Synonyms: 1-(2,5-dimethoxyphenyl)-1-propanon;1-(2,5-Dimethoxyphenyl)-1-propanone;1-(2,5-Dimethoxyphenyl)propanone;1-Propanone, 1-(2,5-dimethoxyphenyl)-;2’,5’-dimethoxy-propiophenon;Propiophenone, 2',5'-dimethoxy-;2,5-DIMETHOXYPROPIOPHENONE;1-(2,5-DINETHOXYPHENYL)-1-PROPANORE
• CAS NO: 5803-30-5
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• EINECS: 227-357-7
• Product Categories: Aromatic Propiophenones (substituted)
• Mol File: 5803-30-5.mol

Chemical Properties

• Melting Point: 8°C
• Boiling Point: 168°C/13mmHg(lit.)
• Flash Point: 121.2°C
• Appearance: /
• Density: 1.047g/cm³
• Vapor Pressure: 0.00189mmHg at 25°C
• Refractive Index: 1.5340 to 1.5380
• CAS DataBase Reference: 2,5-DIMETHOXYPROPIOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHOXYPROPIOPHENONE(5803-30-5)
• EPA Substance Registry System: 2,5-DIMETHOXYPROPIOPHENONE(5803-30-5)

Safety Data

• RTECS: UH0530000
• Hazardous Substances Data: 5803-30-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Dimethoxypropiophenone is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a valuable intermediate in the development of new drugs, contributing to the advancement of medical treatments.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,5-Dimethoxypropiophenone serves as a key component in the preparation of methoxamine hydrochloride, a compound with potential applications in the medical and pharmaceutical industries. Its role in this synthesis process highlights its importance as a versatile and useful building block.
Used in Aromatherapy and Perfumery:
As a component of essential oils found in plants of the Asarum genus, 2,5-Dimethoxypropiophenone is used in the aromatherapy and perfumery industries. Its distinct aroma and properties contribute to the creation of unique fragrances and scents, enhancing the sensory experience for consumers.
Used in Flavor Industry:
2,5-DIMETHOXYPROPIOPHENONE's presence in essential oils also makes it a valuable resource in the flavor industry. It can be used to create and enhance the taste of various food and beverage products, providing a unique flavor profile that can be appreciated by consumers.

Preparation

Obtained by acylation of hydroquinone dimethyl ether,with propionyl chloride in the presence of aluminium chloride in petroleum ether (34%), in carbon disulfide, or using 10% mol. samarium triiodide in acetonitrile (60%)with propionic anhydride in the presence of aluminium chloride in nitromethanewith propionic acid in the presence of PPA at 70° for 2 h (95%)in the presence of zeolite catalyst.

InChI:InChI=1/C11H14O3/c1-4-10(12)9-7-8(13-2)5-6-11(9)14-3/h5-7H,4H2,1-3H3

Upstream product

• 79-03-8 propionyl chloride 
• 150-78-7 1,4-dimethoxybezene 
• 802294-64-0 propionic acid 
• 89106-42-3 1-(2,5-dimethoxyphenyl)propan-1-ol 
• 150-76-5 4-methoxy-phenol 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 123-62-6 propionic acid anhydride 
• 2785-98-0 2,5-dimethoxybenzoic acid 
• 17918-14-8 2,5-dimethoxybenzoyl chloride 
• 1146443-78-8 N,2,5-trimethoxy-N-methylbenzamide 
• 925-90-6 ethylmagnesium bromide 
• 1201-38-3 2',5'-dimethoxyacetophenone 
• 74-83-9 methyl bromide 
• 49710-99-8 1-(2-hydroxy-5-methoxyphenyl)-1-propanone 

Downstream Products

• 38843-85-5 2,5-dimethoxy-1-n-propylbenzene 
• 105254-38-4 3-(2,4-dimethoxy-phenyl)-2-methyl-3-oxo-propionaldehyde 
• 105836-15-5 (R)-(+)-1-(2,5-dimethoxyphenyl)-1-propanol 
• 166446-90-8 (S)-(-)-1-(2,5-dimethoxyphenyl)-1-propanol 
• 127034-30-4 1-(2,5-dimethoxyphenyl)-3-[4-(diethylamino)phenyl]-2-methylprop-2-en-1-one 
• 124711-23-5 (E)-1-(2,5-dimethoxyphenyl)-3-(4-N,N-dimethylaminophenyl)-2-methylprop-2-en-1-one 
• 38843-84-4 2,5-dimethoxy-4-n-propylacetophenone 
• 788825-65-0 (E)-2-methyl-3-(1-tert-butyloxycarbonyl-1H-indol-5-yl)-1-(2,5-dimethoxyphenyl)prop-2-en-1-one 
• 49710-99-8 1-(2-hydroxy-5-methoxyphenyl)-1-propanone 
• 121347-31-7 1-(2,5-dimethoxyphenyl)-2-hydroxyimino-1-acetone 
• 103565-48-6 2,5-dimethoxy-α-aminopropiophenone hydrochloride 

Relevant articles and documents

Method for removing and recovering impurities in methoxylamine hydrochloride synthesis reaction raw material

The invention provides a method for removing and recovering impurities in a methoxylamine hydrochloride synthesis reaction raw material, which belongs to the field of chemical engineering. The methodcomprises the following steps: (1) removal: adding an alkaline reagent into the methoxylamine hydrochloride synthesis reaction raw material, mixing, and separating methyl-removed impurities on one side; and (2) recovery: adding a methylation reagent into the methyl-removed impurities on one side separated in the step (1) to carry out a methylation reaction so as to obtain 2, 5-dimethoxypropiophenone, and recovering the 2, 5-dimethoxypropiophenone. According to the method, the characteristic that phenolic hydroxyl groups in impurities of a methoxylamine hydrochloride synthesis reaction raw material are weakly acidic is utilized, and the alkaline reagent is added to react with methyl-removed impurities on one side to form corresponding salt separation, so that impurities in the raw material2, 5-dimethoxypropiophenone are removed; after the separated impurity sodium salt is methylated again, 2, 5-dimethoxypropiophenone can be obtained again and recycled. The method is simpler and more convenient to operate, high in impurity removal rate and capable of effectively increasing the utilization rate of impurities in raw materials.

DMF Dimethyl Acetal as Carbon Source for α-Methylation of Ketones: A Hydrogenation-Hydrogenolysis Strategy of Enaminones

A novel heterogeneous catalytic hydrogenation-hydrogenolysis strategy has been developed for the α-methylation of ketones via enaminones using DMF dimethyl acetal as carbon source. This strategy provides a very convenient route to α-methylated ketones using a variety of ketones without any base or oxidant. (Chemical Equation Presented).

Pyrazolyl-Based Carboxamides II

The invention relates to pyrazolyl-based carboxamide compounds useful as ICRAC inhibitors, to pharmaceutical compositions containing these compounds and to these compounds for the use in the treatment and/or prophylaxis of diseases and/or disorders, in particular inflammatory diseases and/or inflammatory disorders.

PYRAZOLYL-BASED CARBOXAMIDES II AS CRAC CHANNEL INHIBITORS

The invention relates to pyrazolyl-based carboxamide compounds of formula (I) useful as ICRAC inhibitors, to pharmaceutical compositions containing these compounds and to these compounds for the use in the treatment and/or prophylaxis of diseases and/or disorders, in particular inflammatory diseases and/or inflammatory disorders.

Acylation of aromatic ethers using different carboxylic acid anhydrides as acylating agents in the presence of nontoxic, noncorrosive resin amberlyst 15 as a solid acid catalyst

Friedel-Crafts acylation of aromatic ethers, anisole, 2-methoxynaphthalene, and dimethoxybenzenes with different acid anhydrides is carried out in the presence of an inexpensive and nonhazardous solid acid, Amberlyst 15. The catalyst is reusable, thus making the process environmentally friendly.

Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity

The α-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G2/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 μM; CA4, 0.10 μM) and compete with [3H]colchicine for binding to tubulin (8% [3H]colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity.

Probes for narcotic receptor mediated phenomena. 39. Enantiomeric n-substituted benzofuro[2,3-c]pyridin-6-ols: synthesis and topological relationship to oxide-bridged phenylmorphans

Enantiomers of N-substituted benzofuro[2,3-c]pyridin-6-ols have been synthesized, and the subnanomolar affinity and potent agonist activity of the known racemicN-phenethyl substituted benzofuro[2,3-c]pyridin-6-ol can now be ascribed to the 4aS,9aRenantiomer. The energy-minimized structures suggest that the active enantiomer bears a greater three-dimensional resemblance to morphine than to an ostensibly structurally similar oxide-bridged phenylmorphan. Structural features of the conformers of N-substituted benzofuro[2,3-c]pyridin- 6-ols were compared to provide the rationale for their binding affinity.

Catalytic Friedel-Crafts acylation of aromatic ethers using Sml3

10% mol Sml3 catalysed the Friedel-Crafts acylation of aromatic ethers by acyl chlorides in acetonitrile with the yields of 48-82%. Reactions of various substituted aromatic ethers with acyl chloride were studied. The structures of compounds were established by IR and 1H NMR. The main product obtained with anisole is the para-substituted compound with only a trace (3, a pattern repeated with the other aromatic ethers used.

Phase-vanishing method: Friedel-Crafts acylation of thiophene with tin tetrachloride and its application to convenient parallel synthesis

Phase-vanishing (PV) method was applied to Friedel-Crafts acylations of aromatic compounds with tin tetrachloride as a Lewis acid. The reaction proceeded smoothly and acylation products were obtained in good yield. Parallel, four different Friedel-Crafts acylation reactions were carried out successfully based on the present PV method.

Propenone derivatives

The present invention relates to propenone derivatives represented by the following formula (I): STR1 wherein R1 represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, or YR5 (wherein Y represents S or O; and R5 represents substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a substituted or unsubstituted cyclic ether residue); R2 and R3 independently represent hydrogen, lower alkyl, or substituted or unsubstituted aralkyl, or alternatively R2 and R3 are combined to form substituted or unsubstituted methylene or ethylene; R4 represents hydrogen, hydroxy, lower alkyl, substituted or unsubstituted aralkyl, lower alkoxy, substituted or unsubstituted aralkyloxy, or halogen; and X represents substituted or unsubstituted indolyl; or pharmaceutically acceptable salts thereof.