37592-72-6

Basic information

• Product Name: 4'-N-HEXYLACETOPHENONE
• Synonyms: TIMTEC-BB SBB008299;P-HEXYLACETOPHENONE;1-(4-hexylphenyl)-ethanon;Ethanone, 1-(4-hexylphenyl)-;LABOTEST-BB LT00159052;4'-HEXYLACETOPHENONE;4'-N-HEXYLACETOPHENONE;4-N-HEXYLACETOPHENONE
• CAS NO: 37592-72-6
• Molecular Formula: C₁₄H₂₀O
• Molecular Weight: 204.31
• Product Categories: Acetophenones (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials
• Mol File: 37592-72-6.mol

Chemical Properties

• Boiling Point: 132-135°C 2mm
• Flash Point: 132-135°C/2mm
• Appearance: /
• Density: 0,94 g/cm3
• Vapor Pressure: 0.000668mmHg at 25°C
• Refractive Index: 1.5140
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1942064
• CAS DataBase Reference: 4'-N-HEXYLACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-N-HEXYLACETOPHENONE(37592-72-6)
• EPA Substance Registry System: 4'-N-HEXYLACETOPHENONE(37592-72-6)

Safety Data

• Safety Statements: 24/25
• TSCA: Yes
• Hazardous Substances Data: 37592-72-6(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
4'-N-HEXYLACETOPHENONE is used as a flavoring agent and fragrance ingredient for its sweet, floral scent, contributing to the production of perfumes, soaps, and cosmetics. Its unique olfactory profile enhances the sensory experience of these products, making them more appealing to consumers.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, 4'-N-HEXYLACETOPHENONE serves as an intermediate in the manufacturing process of various drugs and other chemicals. Its chemical properties make it a valuable component in the synthesis of a range of medicinal compounds, thereby playing a crucial role in the development of new pharmaceuticals.
Used in Chemical Production:
Beyond its applications in the flavor and fragrance and pharmaceutical industries, 4'-N-HEXYLACETOPHENONE is also utilized as an intermediate in the production of other chemicals. Its versatility in chemical reactions allows it to be a key component in the synthesis of a variety of chemical products, expanding its utility across different sectors.

InChI:InChI=1/C14H20O/c1-3-4-5-6-7-13-8-10-14(11-9-13)12(2)15/h8-11H,3-7H2,1-2H3

Upstream product

• 1077-16-3 hexylbenzene 
• 75-36-5 acetyl chloride 
• 13329-40-3 4-Iodoacetophenone 
• 96164-66-8 hexyltrifluorosilane 
• 99-90-1 para-bromoacetophenone 
• 108-24-7 acetic anhydride 
• 928-65-4 hexyltrichlorosilane 
• 186581-53-3 diazomethane 
• 50606-95-6 4-hexylbenzoyl chloride 
• 109613-00-5 4-acetophenyl triflate 
• 638-45-9 1-Iodohexane 
• 1626436-23-4 C₆H₁₃I₂In 
• 21369-64-2 n-hexyllithium 
• 111-25-1 1-bromo-hexane 

Downstream Products

• 100963-63-1 1-(4-hexyl-phenyl)-ethanol 
• 554405-51-5 4-(4-hexyl-phenyl)-thiazol-2-ylamine 
• 100-21-0 terephthalic acid 
• 21643-38-9 4-hexylbenzoic acid 
• 99433-28-0 2-bromo-1-(4-cyclohexylphenyl)ethanone 
• 94775-81-2 3-(4-Hexyl-phenyl)-6-propyl-pyridazine 
• 94775-71-0 1-(4-Hexyl-phenyl)-2-hydroxy-heptane-1,4-dione 
• 94775-62-9 Potassium; 2-[2-(4-hexyl-phenyl)-1-hydroxy-2-oxo-ethyl]-3-oxo-hexanoate 
• 81539-69-7 4-(4-hexylphenyl)imidazole-1,2-diamine 
• 81539-72-2 6-(4-Hexyl-phenyl)-imidazo[1,2-b][1,2,4]triazine 
• 81539-66-4 4-(4-Hexyl-phenyl)-N¹-[1-phenyl-meth-(Z)-ylidene]-imidazole-1,2-diamine 
• 81539-74-4 11-(4-Hexyl-phenyl)-9,9a,12,13-tetraaza-cyclopenta[b]triphenylene 

Relevant articles and documents

One-step synthesis of novel flavylium salts containing alkyl side chains in their 3-, 4′-, 5- or 6-positions and their photophysical properties in micellar media

A one-step preparation of several flavylium salts containing alkyl side chains in their 3-, 4′-, 5- or 6-positions is described. Flavylium salts with alkyl side chains in positions 3 or 4′ were isolated from reactions between 2,4-dihydroxybenzaldehyde and

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.

Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions

An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate for indium insertion with equal ease.

Cesium carbonate-catalyzed indium insertion into alkyl iodides and their synthetic utilities in cross-coupling reactions

A catalytic amount of cesium carbonate (10?mol%) was found to be capable of effectively catalyzing the insertion of indium powder into alkyl iodides. The thus-generated alkyl indium reagents could readily undergo palladium-catalyzed cross-coupling reactions with a wide variety of aryl halides, showing compatibility to a range of important functional groups.

Copper(II)-catalyzed preparation of alkylindium compounds and applications in cross-coupling reactions both in aqueous media

An efficient water-based method for the synthesis of alkylindium compound in the presence of a catalytic amount of cheap and readily available CuSO4·5H2O (10 mol%) was developed. The thus-generated alkylindium compounds effectively underwent palladium-catalyzed cross-coupling reactions with a myriad of aryl halides in aqueous media, leading to the cross-coupled products in modest to high yields. The mildness of the formed alkyl organometallics allowed the tolerance to various important functional groups incorporated in both substrates of alkyl iodides and aryl halides.

Cobalt(II)-catalyzed preparation of alkylindium reagents and applications in cross-coupling with aryl halides

The direct insertion of indium powder into alkyl iodides was found to be efficiently catalyzed by a catalytic amount of cobalt(II) bromide (10 mol%). Upon subjection of the thus-formed alkylindium compounds to palladium-catalyzed cross-coupling reactions with a wide range of aryl halides, a series of cross-coupled products could be obtained in moderate to good yields with the tolerance to many important functional groups.

Synthesis of Alkyl Indium Reagents by Using Unactivated Alkyl Chlorides and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions with Aryl Halides

An efficient method for the preparation of alkyl indium reagents by using unactivated and cheap alkyl chlorides as substrates in the presence of indium and LiI was developed. The thus-formed alkyl indium species effectively underwent palladium-catalyzed cross-coupling reactions with aryl halides with wide functional group tolerance.

Study on the design, synthesis and structure-activity relationships of new thiosemicarbazone compounds as tyrosinase inhibitors

52 Structure-based thiosemicarbazone compounds bearing various substituted-lipophilic part, including substituted-benzaldehyde, substituted-phenylalkan-1-one and their biphenyl-type thiosemicarbazone analogs, were designed, synthesized and evaluated as new tyrosinase inhibitors. The results demonstrated that 22 compounds have potent inhibitory activities against tyrosinase with the IC50 value of lower than 1.0 μM. On the basis of the obtained experimental data, the structure-activity relationships (SARs) were rationally derived. Besides, the inhibition mechanism and the inhibitory kinetics of selected compounds 3d and 6e were investigated, revealing that such type of compounds were belonged to the reversible and competitive tyrosinase inhibitors. To verify the safety of these developed thiosemicarbazone compounds, four randomly selected compounds 3d, 4e, 6a and 9a were also tested in 293T cell line for the evaluation of the cytotoxicity. Interestingly, all these compounds almost did not perform any toxicity to 293T cells even at a high concentration of 1000 μmol/L. Taken together, these results suggested that such compounds could serve as the highly efficient and more safe candidates for the treatment of tyrosinase-related disorders.

Phenol Derivatives as Coupling Partners with Alkylsilicates in Photoredox/Nickel Dual Catalysis

Photoredox/nickel dual catalysis via single electron transmetalation allows coupling of Csp3-Csp2 hybridized centers under mild conditions. A procedure for the coupling of electron-deficient aryl triflates, -tosylates, and -mesylates with alkylbis(catecholato)silicates is presented. This method represents the first example of the use of phenol derivatives as electrophilic coupling partners in photoredox/nickel dual catalysis.

Regio-specific polyacetylenes synthesized from anionic polymerizations of template monomers

Substituted polyacetylenes with alkylphenyl side groups and head-to-head regioregularity were prepared through anionic living polymerization of template monomers and subsequent dehydrogenation process. The template monomers have the structure of 2, 3-disubstituted-1, 3-butadienes prepared by palladium-catalyzed Kumada coupling of the corresponding vinyl bromides. Anionic polymerizations of the template monomers produced narrow disperse substituted polybutadiene precursors with exclusive 1, 4-enchainment. The precursors were converted into soluble polyacetylene derivatives via two methods, e.g., bromination followed by elimination of HBr, and direct dehydrogenation by 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (DDQ), both resulting in dark colored products with significant red shift in UV spectra. The obtained head-to-head polyacetylene derivatives exhibited highly thermal stability, possibly due to trans-rich and/or head-to-head chain configurations. The microstructures of the poly(2, 3-dialkylphenyl butadiene) precursors were analyzed in detail using NMR spectroscopy with regard to the solvent effect during polymerization. Block copolymers containing substituted polyacetylene segments were prepared through sequential anionic polymerization of different monomers, followed by dehydrogenation transformation. The present synthesis may serve as a new strategy for tailoring molecular structures of polyacetylene-based polymers by virtue of anionic living polymerization techniques.