645-13-6

Usage

Uses

Used in Perfumery and Flavor Industry:
4'-Isopropylacetophenone is used as a perfuming agent and flavoring agent due to its pleasant odor and warm, spicy flavor. It adds a unique and desirable scent to various products in these industries.
Used in the Synthesis of Indenes:
4'-Isopropylacetophenone serves as a precursor in the one-step synthesis of indenes using a heterogeneous catalyst. This application is particularly relevant in the chemical and pharmaceutical industries, where indenes are valuable intermediates for the production of various compounds.
Occurrence:
4'-Isopropylacetophenone has been reported to be found in the essential oil of lavandin, starfruit, and dried bonito, indicating its natural presence in certain plants and food products.

Preparation

By condensing cymene with acetyl chloride in the presence of AlCl3; also from benzol, acetyl chloride and isopropyl chloride via Friedel–Craft

InChI:InChI=1/C11H14O/c1-8(2)10-4-6-11(7-5-10)9(3)12/h4-8H,1-3H3

Upstream product

• 98-82-8 Isopropylbenzene 
• 108-24-7 acetic anhydride 
• 99-62-7 1,3-diisopropylbenzene 
• 75-36-5 acetyl chloride 
• 18620-03-6 4-isopropylphenylmagnesium bromide 
• 75-05-8 acetonitrile 
• 100-18-5 1,4-bis(1-methylethyl)benzene 
• 4218-48-8 1-ethyl-4-isopropylbenzene 
• 106353-53-1 1-(4-Isopropyl-phenyl)-3,3-di-morpholin-4-yl-propenone 
• 2055-40-5 4-isopropylstyrene 
• 2089-31-8 1-(4-isopropylphenyl)ethan-1-one oxime 
• 7446-70-0 aluminium trichloride 
• 107-06-2 1,2-dichloro-ethane 
• 75-09-2 dichloromethane 

Downstream Products

• 84921-99-3 3t-[2]furyl-1-(4-isopropyl-phenyl)-propenone 
• 1688-53-5 1-(4-isopropyl-phenyl)-3-morpholino-propan-1-one; hydrochloride 
• 1030-52-0 1-(4-isopropyl-phenyl)-3-piperidino-propan-1-one; hydrochloride 
• 107621-06-7 3-hydroxy-1-(4-isopropyl-phenyl)-3,4,4-trimethyl-pentan-1-one 
• 54549-72-3 1-(4-(2-hydroxypropan-2-yl)phenyl)ethan-1-one 
• 4218-48-8 1-ethyl-4-isopropylbenzene 
• 1475-10-1 1-(4-isopropylphenyl)ethanol 
• 3445-42-9 α,α-dimethyl-p-isopropylbenzyl alcohol 
• 1634-63-5 1-(4-isopropyl-3-nitrophenyl)ethan-1-one 
• 32122-03-5 2-(4-isopropyl-phenyl)-3-methyl-butan-2-ol 
• 2089-31-8 1-(4-isopropylphenyl)ethan-1-one oxime 
• 100059-60-7 2-(4-isopropyl-phenyl)-2-oxo-ethanesulfonic acid 
• 713132-14-0 dichloro-acetic acid-(4-isopropyl-phenacylamide) 
• 438531-43-2 6-bromo-2-(4-isopropyl-phenyl)-quinoline-4-carboxylic acid 

Relevant academic research and scientific papers

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%.

Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions

Halogen-bridged methylnaphthyl (MeNAP) palladium dimers are presented as multipurpose Pd-precursors, ideally suited for catalytic method development and preparative organic synthesis. By simply mixing with phosphine or carbene ligands, they are in situ converted into well-defined monoligated complexes. Their catalytic performance was benchmarked against state-of-the-art systems in challenging Buchwald–Hartwig, Heck, Suzuki and Negishi couplings, and ketone arylations. Their use enabled record-setting activities, beyond those achievable by optimization of the ligand alone. The MeNAP catalysts permit syntheses of tetra-ortho-substituted arenes and bulky anilines in near-quantitative yields at room temperature, allow mono-arylations of small ketones, and enable so far elusive cross-couplings of secondary alkyl boronic acids with aryl chlorides.

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.

Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes

Herein we report ketones as feedstock materials in radical cross-coupling reactions under Ni/photoredox dual catalysis. In this approach, simple condensation first converts ketones into prearomatic intermediates that then act as activated radical sources for cross-coupling with aryl halides. Our strategy enables the direct benzylation/benzoylation of (hetero)arenes under mild reaction conditions with high functional group tolerance.

Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands

Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.

Visible-light-promoted site-specific and diverse functionalization of a c(sp3)-c(sp3) bond adjacent to an arene

We report here a strategy for inert C-C bond functionalization. Site-specific cleavage and functionalization of a saturated C(sp3)-C(sp3) bond via a visible-light-induced radical process have been achieved. The general features of this reaction are as follows. (1) Both linear and cyclic C(sp3)-C(sp3) bonds with a vicinal arene can be specifically functionalized. (2) One carbon is converted into a ketone, and another can be tunably converted into nitrile, peroxide, or halide. (3) The typical conditions include 1.0 mol % of Ru(bpy)3Cl2, 1.0 or 5.0 equiv of Zhdankin reagent, white CFL (24 W), open flask, and room temperature. These reactions offer powerful tools to modify carbon skeletons that are intractable by conventional methods. Good selectivity and functional group tolerance, together with mild and open air conditions, make these transformations valuable and attractive.

Facile preparation of 5-alkyl-1-aryltetrazoles with arenes, acyl chlorides, hydroxylamine, and diphenylphosphoryl azide

Successive treatment of arenes with acyl chlorides and AlCl3, the addition of water and removal of solvent, the reaction with NH2OH?HCl and K2CO3, and the reaction with diphenylphosphoryl azide and DBU under warming conditions gave the corresponding 5-alkyl-1-aryltetrazoles efficiently in good to moderate yields. The present method is one-pot transformation of arenes into 5-alkyl-1-aryltetrazoles using the Friedel-Crafts acylation and the Beckmann rearrangement under transition-metal-free conditions.

1,2-Diethoxyethane catalyzed oxidative cleavage of gem-disubstituted aromatic alkenes to ketones under minimal solvent conditions

Aerobic oxidation using pure dioxygen gas as the oxidant has attracted much attention, but its application in synthetic chemistry has been significantly hampered by the complexity of catalytic system and potential risk of high-energy dioxygen gas. By employing 1,2-diethoxyethane as a catalyst and ambient air as an oxidant, an efficient protocol for the construction of various aryl-alkyl and diaryl ketones through oxidative cleavage of gem-disubstituted aromatic alkenes under minimal solvent conditions has been achieved.

Efficient Palladium(0) supported on reduced graphene oxide for selective oxidation of olefins using graphene oxide as a ‘solid weak acid’

Selective oxidation of olefin derivatives to ketones has made innovative development over palladium(0) supported on reduced graphene oxide. Compared to traditional Wacker oxidation, the novel method offers an economical and environment-friendly option by using graphene oxide (GO) as a ‘solid weak acid’ instead of classical homogeneous catalysts like H2SO4 and CF3COOH. X-ray diffraction, X-ray photoelectron spectroscopy, scanning electron microscope and transmission electron microscopy images of Pd0/RGO showed that the nanoscaled Pd particles generated at the flake structure of reduced graphene oxide. Under optimized condition, up to 44 kinds of ketones with different structures can be prepared with excellent yields.

One-Pot Preparation of Aromatic Amides, 4-Arylthiazoles, and 4-Arylimidazoles from Arenes

Simple treatment of arenes with α-bromoacetyl chloride and AlCl3, followed by the reaction with molecular iodine and aq. NH3, thioamides, or amidines gave the corresponding primary aromatic amides, 4-arylthiazoles, or 4-arylimidazoles in good yields, respectively. Aryl α-bromomethyl ketones are the key intermediates in those reactions. Primary aromatic amides were formed from arenes through the reaction of aryl α-bromomethyl ketones with molecular iodine and aq. NH3, and 4-arylthiazoles and 4-arylimidazoles were formed from arenes through the reactions of aryl α-bromomethyl ketones with thioamides and amidines, respectively, in one pot under transition-metal-free conditions.