6008-36-2

Usage

Uses

Used in Surfactant Industry:
N-NONANOPHENONE is used as a key intermediate in the synthesis of novel alkylbenzene sulfonate gemini surfactants. Gemini surfactants are a class of surfactants that consist of two hydrophobic tails and two hydrophilic head groups connected by a spacer. They exhibit unique properties, such as lower critical micelle concentration, higher surface activity, and better solubilizing ability compared to conventional surfactants. These properties make them suitable for various applications, including detergency, emulsification, and stabilization of dispersions.
In the synthesis of alkylbenzene sulfonate gemini surfactants, N-NONANOPHENONE serves as a starting material to form the hydrophobic tails of the surfactant molecules. The resulting gemini surfactants can be used in various industries, such as detergents, personal care products, and oil recovery, due to their enhanced performance compared to traditional surfactants.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 788, 1990 DOI: 10.1021/jo00290a004Tetrahedron Letters, 37, p. 2197, 1996 DOI: 10.1016/0040-4039(96)00258-4

InChI:InChI=1/C15H22O/c1-2-3-4-5-6-10-13-15(16)14-11-8-7-9-12-14/h7-9,11-12H,2-6,10,13H2,1H3

Upstream product

• 764-85-2 Nonanoyl chloride 
• 57716-72-0 1-phenylnonan-1-ol 
• 17049-49-9 octylmagnesium bromide 
• 100-47-0 benzonitrile 
• 112-05-0 nonanoic acid 
• 65-85-0 benzoic acid 
• 71-43-2 benzene 
• 104-53-0 3-phenyl-propionaldehyde 
• 93-58-3 benzoic acid methyl ester 
• 629-05-0 n-octyne 
• 591-50-4 iodobenzene 
• 629-27-6 1-Iodooctane 
• 201230-82-2 carbon monoxide 
• 111-66-0 oct-1-ene 

Downstream Products

• 1081-77-2 n-nonylbenzene 
• 23302-85-4 3-hydroxy-3-phenyl-undecanoic acid 
• 67267-88-3 6-Phenyl-n-tetradecanol-⁽⁶⁾ 
• 92779-85-6 1-phenylnonan-1-amine 
• 140472-48-6 1,1-dibromo-2-phenyldec-1-ene 
• 440365-04-8 4-phenyldodecan-4-ol 
• 132559-71-8 (E)-1-phenylnon-2-en-1-one 
• 16664-50-9 1-phenyl-1-decyne 
• 4534-55-8 6-phenyltetradecane 
• 94681-77-3 6-Phenyl-n-tetradecen 

Relevant academic research and scientific papers

Preparation of Primary and Secondary Dialkylmagnesiums by a Radical I/Mg-Exchange Reaction Using sBu2Mg in Toluene

The treatment of primary or secondary alkyl iodides with sBu2Mg in toluene (25–40 °C, 2–4 h) provided dialkylmagnesiums that underwent various reactions with aldehydes, ketones, acid chlorides or allylic bromides. 3-Substituted secondary cyclohexyl iodides led to all-cis-3-cyclohexylmagnesium reagents under these exchange conditions in a highly stereoconvergent manner. Enantiomerically enriched 3-silyloxy-substituted secondary alkyl iodides gave after an exchange reaction with sBu2Mg stereodefined dialkylmagnesiums that after quenching with various electrophiles furnished various 1,3-stereodefined products including homo-aldol products (99 % dr and 98 % ee). Mechanistic studies confirmed a radical pathway for these new iodine/magnesium-exchange reactions.

Ir(NHC)-Catalyzed Synthesis of β-Alkylated Alcohols via Borrowing Hydrogen Strategy: Influence of Bimetallic Structure

Multi N-heterocyclic carbene(NHC)-modified iridium catalysts were employed in the β-alkylation of alcohols; dimerization of primary alcohols (Guerbet reaction), cross-coupling of secondary and primary alcohols, and intramolecular cyclization of alcohols. Mechanistic studies of Guerbet reaction, including kinetic experiments, mass analysis, and density functional theory (DFT) calculation, were employed to explain the fast reaction promoted by bimetallic catalysts, and the dramatic reactivity increase of monometallic catalysts at the late stage of the reaction. (Figure presented.).

LIGHT INDUCED CATALYTIC C-H OXYGENATION OF ALKANES

A method of oxygenating a benzylic C-H bond is provided. The method comprises light induced activation of an initiator and subsequent reaction with oxygen, resulting in the formation of free radicals. Subsequently, free radicals catalyze the reaction of the benzylic C-H bond with oxygen, thereby forming an oxygenated compound.

Synthesis of α-Alkylated Ketones via Selective Epoxide Opening/Alkylation Reactions with Primary Alcohols

A new method for converting terminal epoxides and primary alcohols into α-alkylated ketones under borrowing hydrogen conditions is reported. The procedure involves a one-pot epoxide ring opening and alkylation via primary alcohols in the presence of an N-heterocyclic carbene iridium(I) catalyst, under aerobic conditions, with water as the side product.

Visible-Spectrum Solar-Light-Mediated Benzylic C-H Oxygenation Using 9,10-Dibromoanthracene As an Initiator

We report a visible-light-mediated benzylic C-H oxygenation reaction. The reaction is initiated by solar light or the blue LED activation of 9,10-dibromoanthracene in a reaction with oxygen and takes place at ambient temperature and air pressure. Secondary benzylic positions are oxygenated to ketones, while tertiary benzylic carbons are oxygenated to give hydroperoxides. Notably, cumene hydroperoxide is produced in a higher yield and at milder conditions than the currently employed industrial conditions.

Synthesis and catalytic applications of Ru and Ir complexes containing N,O-chelating ligand

A series of monometallic complexes (Ru1–3, Ir1–3) which have N,O-chelating ligand (pyrazine-2-carboxylate (1), pyridine-2-carboxylate (2), quinoline carboxylate(3) and bimetallic complexes (Ru4,5, Ir4,5) bridged by pyrazine-2,3- dicarboxylate (4) and imidazole-4,5-dicarboxylate(5) were synthesized and characterized by 1H-, 13C NMR, FT-IR, and elemental analysis. The crystal structure of Ir2 was determined by X-ray crystallography. The complexes (Ru1–5, Ir1–5) were applied to investigate the electronic and steric effect of ligand in their catalytic activities in transfer hydrogenation and alpha(α)-alkylation reaction of ketones with alcohols. The activities of iridium complexes (Ir1–5) were much more efficient than ruthenium complexes (Ru1–5). The highest activity for both reactions was observed for the complex (Ir2) with pyridine-2-carboxylate. The Ir hydride species was monitored for both reactions.

C-C coupling formation using nitron complexes

A series of RuII (1), RhIII (2), IrIII (3, 4), IrI (5) and PdII (6-9) complexes of the 'instant carbene' nitron were prepared and characterized by 1H- and 13C-NMR, FT-IR and elemental analysis. The molecular structures of complexes 1-4 and 6 were determined by X-ray diffraction studies. The catalytic activity of the complexes (1-9) was evaluated in alpha(α)-alkylation reactions of ketones with alcohol via the borrowing hydrogen strategy under mild conditions. These complexes were able to perform this catalytic transformation in a short time with low catalyst and base amounts under an air atmosphere. Also, the PdII-nitron complexes (6-9) were applied in the Suzuki-Miyaura C-C coupling reaction and these complexes successfully initiated this reaction in a short time (30 minutes) using the H2O/2-propanol (1.5?:?0.5) solvent system. The DFT calculations revealed that the Pd0/II/0 pathway was more preferable for the mechanism

Stereodivergent synthesis of alkenes by controllable syn-/anti-fragmentation of β-hydroxysulfonyl intermediates

The reduction of the carbonyl group in acylated trifluoroethyl alkanesulfonates follows the Felkin-Ahn selectivity, and the so-formed diastereomeric β-hydroxysulfonyl intermediates undergo syn- and anti-fragmentation, depending on the reaction conditions. In effect, isomeric E- and Z-alkenes are formed in a stereodivergent manner, which mimics the mechanistic manifold of the Peterson olefination.

Piano-stool Ru (II) arene complexes that contain ethylenediamine and application in alpha-alkylation reaction of ketones with alcohols

A series of piano-stool Ru (II) complexes (Ru1–7) bearing ethylenediamine with aryl and aliphatic groups were prepared and fully characterized by 1H, 13C, 19F and 31P NMR spectroscopy, FT-IR and elemental analysis. The crystal structures of Ru2–4 and Ru7 were determined by X-ray crystallography. They were successfully applied to the alpha(α)-alkylation of aliphatic and aromatic ketones with alcohols via the borrowing hydrogen strategy in mild reaction conditions within a short time. The catalytic system has a broad substrate scope, which allows the synthesis of alpha alkylated ketones with excellent yields. The electronic and steric effects of complexes on catalytic activity were analysed. The influence of the carbon chain length of the ligand on the alpha-alkylation reaction of ketones was also investigated. The catalytic cycle was also examined by 1H-NMR spectroscopy in d8-toluene.

Nickel-Catalyzed Alkylation of Ketone Enolates: Synthesis of Monoselective Linear Ketones

Herein we have developed a Ni-catalyzed protocol for the synthesis of linear ketones. Aryl, alkyl, and heteroaryl ketones as well as alcohols yielded the monoselective ketones in up to 90% yield. The catalytic protocol was successfully applied in to a gram-scale synthesis. For a practical utility, applications of a steroid derivative, oleyl alcohol, and naproxen alcohol were employed. Preliminary catalytic investigations involving the isolation of a Ni intermediate and defined Ni-H species as well as a series of deuterium-labeling experiments were performed.