5736-89-0

Usage

Uses

Used in Research and Development:
4'-BUTOXYACETOPHENONE is used as a research chemical for the synthesis of various compounds, including 3,5-di-(4-butoxyphenyl)-1H-pyrazole, (E)-1-(4-butoxyphenyl)-3-phenylprop-2-en-1-one, and 5-aryl-6H-1,3,4-thiadiazine. These synthesized compounds can be further explored for their potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4'-BUTOXYACETOPHENONE may be used as a key intermediate in the synthesis of various drugs and drug candidates. Its electron-enriched nature allows for the formation of new chemical entities with potential therapeutic properties.
Used in Chemical Synthesis:
4'-BUTOXYACETOPHENONE is used as a starting material or intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable component in the development of new molecules with specific applications in various fields, such as materials science, agrochemicals, and specialty chemicals.

InChI:InChI=1/C12H16O2/c1-3-4-9-14-12-7-5-11(6-8-12)10(2)13/h5-8H,3-4,9H2,1-2H3

Upstream product

• 1126-79-0 n-butyl phenyl ether 
• 108-24-7 acetic anhydride 
• 99-90-1 para-bromoacetophenone 
• 71-36-3 butan-1-ol 
• 542-69-8 1-iodo-butane 
• 99-93-4 4-Hydroxyacetophenone 
• 100-67-4 potassium phenolate 
• 4766-57-8 tetra(n-butoxy)silane 
• 99-89-8 4-Isopropylphenol 
• 28530-37-2 1-butoxy-4-isopropylbenzene 
• 2550-26-7 4-Phenyl-2-butanone 
• 105365-51-3 4-butoxyphenylboronic acid 
• 3524-86-5 1-(4-(4-bromobutoxy)phenyl)ethan-1-one 
• 123-07-9 4-Ethylphenol 

Downstream Products

• 24239-62-1 1-(4-butoxy-phenyl)-3-dimethylamino-propan-1-one; hydrochloride 
• 74980-02-2 1-(4-butoxy-phenyl)-3-diethylamino-propan-1-one; hydrochloride 
• 536-43-6 dyclonine HCl 
• 92595-22-7 [1-(4-Butoxy-phenyl)-eth-(E)-ylidene]-phenyl-amine 
• 91553-11-6 α-<4-Butyloxy-phenyl>-aethylamin 
• 14333-54-1 4-Butyloxy-phenylglyoxal 
• 192573-75-4 3-(4-(butoxy)phenyl)-1H-pyrazole 
• 82935-13-5 1-(4-butoxy-phenyl)-3-morpholin-4-yl-propan-1-one 
• 642082-94-8 2-acetyl-4'-n-butoxyacetophenone 
• 642082-92-6 4'-n-butoxy-3-(dimethylamino)acrylophenone 
• 881735-40-6 2-[3-(4-butoxyphenyl)pyrazol-1-yl]pyridine 
• 88858-28-0 4-Butyloxy-acetophenon-semicarbazon 

Relevant academic research and scientific papers

Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes

An electrochemistry-promoted oxidative cleavage of (sp3)C-C(sp3)/H bonds in alkylarenes was developed. Various aryl alkanes can be smoothly converted into ketones/aldehydes under aerobic conditions using a user-friendly undivided cell setup. The features of air as oxidant, scalability, and mild conditions make them attractive in synthetic organic chemistry.

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.

Defunctionalization of sp3 C–Heteroatom and sp3 C–C Bonds Enabled by Photoexcited Triplet Ketone Catalysts

A general strategy for enabling a light-induced defunctionalization of sp3 C–heteroatom and sp3 C–C bonds with triplet ketone catalysts and bipyridine additives is disclosed. This protocol is characterized by its broad scope without recourse to transition metal catalysts or stoichiometric exogeneous reductants, thus offering a complementary technique for activating σ sp3 C–C(heteroatom) bonds. Preliminary mechanistic studies suggest that the presence of 2,2′-bipyridines improves the lifetime of ketyl radical intermediates.

Discovery and characterization of a novel perylenephotoreductant for the activation of aryl halides

To develop a photocatalyst with catalytical activity for substrates with low reactivities is always highly desired. Herein, based on the principle of structure–property relationships, we rationally designed the natural product cercosporin, the naturally occurring perylenequinonoid pigment, to develop a novel organic perylenephotoreductant, hexacetyl reduced cercosporin (HARCP), through structural manipulation. Compared with cercosporin, HARCP shows prominent electrochemical and photophysical characteristics with greatly improved photoreductive activity, fluorescence lifetime and fluorescence quantum yield. These properties allowed HARCP as a powerful photoreductant to efficiently realize a series of benchmark reactions, including photoreduction, alkoxylation and hydroxylation to construct C–H and C–O bonds using aryl halides as substrates under mild conditions, all of which have never been achieved by the same photocatalyst. Thus, this study well supports the notion that the principle between structural manipulation and photocatalytic activity is of great significance to design customized photocatalysts for photoredox chemistry.

Development of Trifluoromethanesulfonic Acid-Immobilized Nitrogen-Doped Carbon-Incarcerated Niobia Nanoparticle Catalysts for Friedel-Crafts Acylation

Heterogeneous trifluoromethanesulfonic acid-immobilized nitrogen-doped carbon-incarcerated niobia nanoparticle catalysts (NCI-Nb-TfOH) that show excellent catalytic performance with low niobium loading (1 mol %) in Friedel-Crafts acylation have been developed. These catalysts exhibit higher activity and higher tolerance to catalytic poisons compared with the previously reported TfOH-treated NCI-Ti catalysts, leading to a broader substrate scope. The catalysts were characterized via spectroscopic and microscopic studies.

Site-Specific Oxidation of (sp3)C-C(sp3)/H Bonds by NaNO2/HCl

A site-specific oxidation of (sp3)C-C(sp3) and (sp3)C-H bonds in aryl alkanes by the use of NaNO2/HCl was explored. The method is chemical-oxidant-free, transition-metal-free, uses water as the solvent, and proceeds under mild conditions, making it valuable and attractive to synthetic organic chemistry.

Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a NiII-Aryl Complex

A highly effective C?O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a NiII-aryl complex under long-wave UV (390–395 nm) irradiation in the presence of a soluble amine base without any additional photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary and secondary aliphatic alcohols, affording synthetically important ethers. Intramolecular C?O coupling is also possible. The reaction appears to proceed via a NiI–NiIII catalytic cycle.

Design, synthesis, biological evaluation and inhibition mechanism of 3-/4-alkoxy phenylethylidenethiosemicarbazides as new, potent and safe tyrosinase inhibitors

Tyrosinase plays important roles in many different disease related processes, and the development of its inhibitors is particularly important in biotechnology. In this study, thirty-nine 3-/4-alkoxyphenylethyli-denethiosemicarbazides were synthesized as novel tyrosinase inhibitors based on structure-based molecular design. Our experimental results demonstrated that thirty-one of them possess remarkable tyrosinase inhibitory activities with IC50 value below 1μM, and 5a, 6e, 6g and 6t did not display any toxicity to 293T cell line at the concentration of 1000μmol/L. According to the inhibitory activities, several compounds were selected for detail investigation on the structure–activity relationships (SARs), mechanisms of enzyme inhibition, inhibitory kinetics and cytotoxicity. In particular, the interaction between the selected inhibitors and the active center of tyrosinase was considered and discussed in detail based on their structural characteristics. Taken together, the results presented here demonstrated that the newly designed compounds are promising candidates for the treatment of tyrosinase-related disorders and further development of them may have significant contribution in biomedical science.

Design, synthesis, docking studies and monoamine oxidase inhibition of a small library of 1-acetyl- and 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazoles

New N-acetyl/N-thiocarbamoylpyrazoline derivatives were designed and synthesized in high yields to assess their inhibitory activity and selectivity against human monoamine oxidase A and B. The most important chiral compounds were separated into their single enantiomers and tested. The impact of the substituents at N1, C3 and C5 positions as well the influence of the configuration of the C5 on the biological activity were analyzed. Bulky aromatic groups at C5 were not tolerated. p-Prenyloxyaryl moiety at C3 oriented the selectivity toward the B isoform. The results were also corroborated by molecular modelling studies providing new suggestions for the synthesis of privileged structures to serve as lead compounds for the treatment of mood disorders and neurodegenerative diseases.

Long-Lived Charge-Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer

Here we investigate the photophysics and photochemistry of Ni(II) aryl halide complexes common to cross-coupling and Ni/photoredox reactions. Computational and ultrafast spectroscopic studies reveal that these complexes feature long-lived 3MLCT excited states, implicating Ni as an underexplored alternative to precious metal photocatalysts. Moreover, we show that 3MLCT Ni(II) engages in bimolecular electron transfer with ground-state Ni(II), which enables access to Ni(III) in the absence of external oxidants or photoredox catalysts. As such, it is possible to facilitate Ni-catalyzed C-O bond formation solely by visible light irradiation, thus representing an alternative strategy for catalyst activation in Ni cross-coupling reactions.