1835-05-8

Usage

Uses

Used in Pharmaceutical Synthesis:
2-bromo-3-4-dimethoxypropiophenone is utilized as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for versatile reactions and modifications, facilitating the creation of diverse medicinal compounds.
Used in Organic Compound Synthesis:
In the field of organic chemistry, 2-bromo-3-4-dimethoxypropiophenone serves as a key intermediate for the synthesis of a wide range of organic compounds. Its reactivity and functional groups enable chemists to explore various synthetic pathways, leading to the production of novel and useful organic molecules.
Used in Medicinal Chemistry Research:
2-bromo-3-4-dimethoxypropiophenone plays a significant role in medicinal chemistry research, where it is employed to investigate the structure-activity relationships of potential drug candidates. Its presence in various synthetic pathways allows researchers to probe the effects of structural modifications on the biological activity of compounds, thereby advancing the understanding of drug design principles.
Used in Drug Discovery:
2-bromo-3-4-dimethoxypropiophenone is also used in drug discovery processes, where it serves as a starting material or a building block for the development of new pharmaceutical agents. Its potential applications in medicinal chemistry make it an important chemical for various research and development purposes, driving the innovation of new treatments and therapies.

InChI:InChI=1/C11H13BrO3/c1-7(12)11(13)8-4-5-9(14-2)10(6-8)15-3/h4-7H,1-3H3

Upstream product

• 1835-04-7 ethyl 3,4-dimethoxyphenyl ketone 
• 91-16-7 1,2-dimethoxybenzene 

Downstream Products

• 88497-90-9 4-[2-(3,4-Dimethoxy-phenyl)-1-methyl-2-oxo-ethoxy]-3-methoxy-benzoic acid methyl ester 
• 4962-37-2 1-(3,4-dimethoxyphenyl)-2-bromopropan-1-ol 
• 92311-14-3 1-<1-(3,4-dimethoxybenzoyl)ethyl>-4-(2-oxo-1,2,3,4-tetrahydro-3-quinazolinylmethyl)piperidine 
• 79106-37-9 1-<2-oxo-2-(3,4-dimethoxyphenyl)-1-methylethyl>-4-(1,2,3,4-tetrahydro-2-oxo-1-quinazolinyl)piperidine 
• 79106-52-8 1-[1-(3,4-dimethoxybenzoyl)-ethyl]-4-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidine 
• 85732-45-2 C₂₃H₂₆N₂O₅ 
• 79106-74-4 1-<3-(3,4-dimethoxyphenyl)-3-oxo-2-propyl>-4-(2-oxoindolin-3-yl)piperidine 
• 121061-08-3 1-<2-(3,4-dimethoxyphenyl)-1-methyl-2-oxoethyl>-3'-methyl-spiro-2'(1'H)-one 
• 87120-87-4 1-(3,4-Dimethoxy-phenyl)-2-[4-(2-ethoxy-benzoimidazol-1-yl)-piperidin-1-yl]-propan-1-one 
• 79106-66-4 3-{1-[2-(3,4-Dimethoxy-phenyl)-1-methyl-2-oxo-ethyl]-piperidin-4-yl}-3,4-dihydro-quinazolin-2-yl-cyanamide 
• 79106-31-3 1-<2-oxo-2-(3,4-dimethoxyphenyl)-1-methylethyl>-4-(1,2,3,4-tetrahydro-2-oxo-3-quinazolinyl)piperidine 
• 79122-23-9 1-(3,4-Dimethoxy-phenyl)-2-[4-(2-methyl-benzoimidazol-1-yl)-piperidin-1-yl]-propan-1-one 
• 93289-63-5 1-(3',4'-dimethoxyphenyl)-2-(2-methoxy-4-allyl-phenoxy)propan-1-one 
• 148149-52-4 4-[2-(3,4-Dimethoxy-phenyl)-1-methyl-2-oxo-ethoxy]-3-hydroxy-5-methoxy-benzoic acid methyl ester 

Relevant academic research and scientific papers

Reactivity of substrates with multiple competitive reactive sites toward NBS under neat reaction conditions promoted by visible light

Regioselectivity of visible-light-induced transformations of a range of (hetero)aryl alkyl-substituted ketones bearing several competitive reactive sites (α-carbonyl, benzyl and aromatic ring) with N-bromosuccinimide (NBS) was studied under solvent-free reaction conditions (SFRC) and in the absence of inert-gas atmosphere, radical initiators and catalysts. An 8-W energy-saving household lamp was used for irradiation. Heterogeneous reaction conditions were dealt with throughout the study. All substrates were mono- or dibrominated at the α-carbonyl position, and additionally, some benzylic or aromatic bromination was observed in substrates with benzylic carbon atoms or electron-donating methoxy groups, respectively. Surprisingly, ipso-substitution of the acyl group with a bromine atom took place with (4-methoxynaphthyl) alkyl ketones. While the addition of the radical scavenger TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxy) decreased the extent of α- and ring bromination, it completely suppressed the benzylic bromination and α,α-dibromination with NBS under SFRC.

Selective cleavage of the Cα-Cβ linkage in lignin model compounds via Baeyer-Villiger oxidation

Lignin is an amorphous aromatic polymer derived from plants and is a potential source of fuels and bulk chemicals. Herein, we present a survey of reagents for selective stepwise oxidation of lignin model compounds. Specifically, we have targeted the oxidative cleavage of Cα-Cβ bonds as a means to depolymerize lignin and obtain useful aromatic compounds. In this work, we prepared several lignin model compounds that possess structures, characteristic reactivity, and linkages closely related to the parent lignin polymer. We observed that selective oxidation of benzylic hydroxyl groups, followed by Baeyer-Villiger oxidation of the resulting ketones, successfully cleaves the Cα-Cβ linkage in these model compounds. This journal is

Synthesis of nordihydroguaiaretic acid derivatives and their bioactivities on S. pombe and K562 cell lines

Nordihydroguaiaretic acid (NDGA) and its synthetic analogues are potentially useful in treating diseases related to cancers, diabetes, viral and bacterial infections, and inflammation. In this paper, we report the optimal synthetic methods and the bioactivity study of terameprocol 2, NDGA derivative 3, and its cyclized analogue 4. The IC50 of these three compounds 2, 3 and 4 on the growth metabolism of Schizosacchromyces pombe and K562 cell lines were determined by microcalorimetry. The preliminary results showed that the compounds 2, 3 and 4 possessed good inhibition activities on S. pombe and K562 cell lines, and exhibited bidirectional biological effect and Hormesis effect. In particular, terameprocol 2 was found to possess the most potent inhibitory effect on K562 cell lines.

SCALABLE SYNTHETIC PROCESS FOR MAKING TERAMEPROCOL

A manufacturing process for making terameprocol (1) which includes the following reaction scheme, wherein a first general reaction is the formation of a furan intermediate (39) and a second general reaction is the ring-reduction and ring-opening of the furan intermediate (39) to form the terameprocol (1)

Generation and reactivity of ketyl radicals with lignin related structures. On the importance of the ketyl pathway in the photoyellowing of lignin containing pulps and papers

(Chemical Equation Presented) Ketyl radicals with lignin related structures have been generated by means of radiation chemical and photochemical techniques. In the former studies ketyl radicals are produced by reaction of α-carbonyl-β-aryl ether lignin models with the solvated electron produced by pulse radiolysis of an aqueous solution at pH 6.0. The UV-vis spectra of ketyl radicals are characterized by three main absorption bands. The shape and position of these bands slightly change when the spectra are recorded in alkaline solution (pH 11.0) being now assigned to the ketyl radical anions and a pKa = 9.5 is determined for the 1-(3,4,5-trimethoxyphenyl)-2- phenoxyethanol-1-yl radical. Decay rates of ketyl radicals are found to be dose dependent and, at low doses, lie in the range (1.7-2.7) × 103 s-1. In the presence of oxygen a fast decay of the ketyl radicals is observed (k2 = 1.8-2.7 × 109 M-1 s -1) that is accompanied by the formation of stable products, i.e., the starting ketones. In the photochemical studies ketyl radicals have been produced by charge-transfer (CT) photoactivation of the electron donor-acceptor salts of methyl viologen (MV2+) with α-hydroxy-α- phenoxymethylaryl acetates. This process leads to the instantaneous formation of the reduced acceptor (methyl viologen radical cation, MV+?), as is clearly shown in a laser flash photolysis experiment by the two absorption bands centered at 390 and 605 nm, and an acyloxyl radical [ArC(CO 2?)(OH)CH2(OC6H5)], which undergoes a very fast decarboxylation with formation of the ketyl radicals. Steady-state photoirradiation of the CT ion pairs indicates that 1-aryl-2-phenoxyethanones are formed as primary photoproducts by oxidation of ketyl radicals by MV2+ (under argon) or by molecular oxygen. Small amounts of acetophenones are formed by further photolysis of 1-aryl-2-phenoxyethanones and not by β-fragmentation of the ketyl radicals. The high reactivity of ketyl radicals with oxygen coupled with the low rates of β-fragmentation of the same species have an important bearing in the context of the photoyellowing of lignin containing pulps and papers.

Electroorganic Reactions. 38. Mechanism of Electrooxidative Cleavage of Lignin Model Dimers

The mechanisms for oxidative cleavage of several phenolic ethers, models for lignins, have been investigated by a detailed comparison of the results of anodic oxidation at nickel anodes in alkaline electrolyte with that of oxidation in acetonitrile in the presence of a triarylamine redox catalyst.The latter reaction is unambiguously initiated by single-electron transfer (SET), and in this case the major product of cleavage is aldehyde (vanillin or syringaldehyde derivatives).At nickel anodes polymerization is predominant although the aldehydes are formed together with larger amounts of the corresponding carboxylic acids.Combinations of 4-hydroxyl, α-keto, β-O-aryl, and β-hydroxymethyl functionality are shown to be crucial for the oxidation at nickel; the carboxylic acid formation probably involves a route with initial hydrogen atom abstraction at the surface.Important chemical conversions precede and accompany oxidation in alkaline media, and these are associated with the propensity for polymerization.

Cyclization of Diketones to Pyridazine and Furan Derivatives

Condensation of (+/-)-2,3-bis(3,4-dimethoxybenzoyl)butane-1,4-dione 1 with different hydrazine bases afforded the corresponding pyridazines 2 and 3.Refluxing the diketone 1 with methanolic hydrogen chloride yielded the corresponding 3,4-dimethylfuran derivative 5.Reaction of acetonylacetone 6 with p-sulfamylphenylhydrazine afforded the corresponding 3,6-dimethyl-1H-pyridazine derivative 7.Reaction of 7 with the appropriate isocyanate and isothiocyanate yielded the corresponding benzenesulfonylurea 8 and thiourea 9 derivatives respectively.The structures of the compounds synthesized were affirmed by microanalyses and spectral studies.