502-56-7

Usage

Safety Profile

Moderately toxic by ingestion andintravenous routes. A flammable liquid. When heated todecomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C9H18O/c1-3-5-7-9(10)8-6-4-2/h3-8H2,1-2H3

Upstream product

• 623-93-8 5-nonanol 
• 7367-38-6 5-butyl-4-nonene 
• 96610-56-9 3-oxo-2-propyl-heptanoic acid ethyl ester 
• 2032-75-9 2,2-dichloro-1,3-benzodioxole 
• 122-56-5 tributyl borane 
• 2082-59-9 pentanoic anhydride 
• 88626-90-8 BuMnCl 
• 127705-08-2 trans-<8-(2,2-dibutyl-5-octyl-1,3-dioxolan-4-yl)octyl>trimethylammonium methanesulfonate 
• 76467-38-4 2,2-dibutyl-1,3-dithiane 
• 54661-97-1 2,2-dibutyl-[1,3]dioxolane 
• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 124-38-9 carbon dioxide 
• 109-52-4 valeric acid 

Downstream Products

• 5340-52-3 5-propylnonan-5-ol 
• 1120-07-6 nonanamide 
• 409321-22-8 nonan-5-one-hydrazone 
• 623-93-8 5-nonanol 
• 61295-53-2 4-chloro-5-nonanone 
• 14717-30-7 (E)-1-chloro-2-(pent-1-en-1-yl)benzene 
• 19969-04-1 1-phenyl-heptan-3-one 
• 109-52-4 valeric acid 
• 7774-47-2 5,5-dibutyldihydrofuran-2(3H)-one 
• 1530-11-6 1,1-diphenyl-pent-1-ene 
• 81392-97-4 (E)-1-methyl-4-(pent-1-en-1-yl)benzene 
• 18657-10-8 (E)-1-methoxy-4-(pent-1-en-1-yl)benzene 

Relevant academic research and scientific papers

Kinetics of Valeric Acid Ketonization and Ketenization in Catalytic Pyrolysis on Nanosized SiO2, γ-Al2O3, CeO2/SiO2, Al2O3/SiO2 and TiO2/SiO2

Valeric acid is an important renewable platform chemical that can be produced efficiently from lignocellulosic biomass. Upgrading of valeric acid by catalytic pyrolysis has the potential to produce value added biofuels and chemicals on an industrial scale. Understanding the different mechanisms involved in the thermal transformations of valeric acid on the surface of nanometer-sized oxides is important for the development of efficient heterogeneously catalyzed pyrolytic conversion techniques. In this work, the thermal decomposition of valeric acid on the surface of nanoscale SiO2, γ-Al2O3, CeO2/SiO2, Al2O3/SiO2 and TiO2/SiO2 has been investigated by temperature-programmed desorption mass spectrometry (TPD MS). Fourier transform infrared spectroscopy (FTIR) has also been used to investigate the structure of valeric acid complexes on the oxide surfaces. Two main products of pyrolytic conversion were observed to be formed depending on the nano-catalyst used—dibutylketone and propylketene. Mechanisms of ketene and ketone formation from chemisorbed fragments of valeric acid are proposed and the kinetic parameters of the corresponding reactions were calculated. It was found that the activation energy of ketenization decreases in the order SiO2>γ-Al2O3>TiO2/SiO2>Al2O3/SiO2, and the activation energy of ketonization decreases in the order γ-Al2O3>CeO2/SiO2. Nano-oxide CeO2/SiO2 was found to selectively catalyze the ketonization reaction.

Boosting activity of molecular oxygen by pyridinium-based photocatalysts for metal-free alcohol oxidation

An eco-friendly and economical approach for the photocatalytic oxidation of organic inter-mediates by air under mild conditions is highly desirable in green and sustainable chemistry, where the photogeneration of active oxygen species plays a key role in improving conversion efficiency and selectivity. By using pyridinium derivatives as molecular mediators for electron transfer and energy transfer, the simultaneous activation of O2from air into superoxide radicals and singlet oxygen species can be achieved, and a photoinduced electron transfer catalytic system for the oxidation of alcohols has been developed. Thus, we have successfully simplified the complicated catalytic system into a single molecular catalyst without any additional noble metals and co-catalysts/additives. The current photocatalytic system shows high catalytic efficiency not only for aromatic alcohols but also for aliphatic alcohols that are generally difficult to undergo aerobic oxidation at room temperature under air atmosphere, representing an ideal photocatalytic platform for green and economical organic syntheses.

Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides

Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.

Fast Addition of s-Block Organometallic Reagents to CO2-Derived Cyclic Carbonates at Room Temperature, Under Air, and in 2-Methyltetrahydrofuran

Fast addition of highly polar organometallic reagents (RMgX/RLi) to cyclic carbonates (derived from CO2 as a sustainable C1 synthon) has been studied in 2-methyltetrahydrofuran as a green reaction medium or in the absence of external volatile organic solvents, at room temperature, and in the presence of air/moisture. These reaction conditions are generally forbidden with these highly reactive main-group organometallic compounds. The correct stoichiometry and nature of the polar organometallic alkylating or arylating reagent allows straightforward synthesis of: highly substituted tertiary alcohols, β-hydroxy esters, or symmetric ketones, working always under air and at room temperature. Finally, an unprecedented one-pot/two-step hybrid protocol is developed through combination of an Al-catalyzed cycloaddition of CO2 and propylene oxide with the concomitant fast addition of RLi reagents to the in situ and transiently formed cyclic carbonate, thus allowing indirect conversion of CO2 into the desired highly substituted tertiary alcohols without need for isolation or purification of any reaction intermediates.

One-pot direct conversion of levulinic acid into high-yield valeric acid over a highly stable bimetallic Nb-Cu/Zr-doped porous silica catalyst

The direct conversion of levulinic acid (LA) to valeric biofuel is highly promising for the development of biorefineries. Herein, LA is converted into valeric acid (VA) via one-pot direct cascade conversion over non-noble metal-based Nb-doped Cu on Zr-doped porous silica (Nb-Cu/ZPS). Under mild reaction conditions (150 °C and 3.0 MPa H2 for 4 h), LA was completely converted into VA in high yield (99.8%) in aqueous medium with a high turnover frequency of 0.038 h-1. The Lewis acid sites of ZPS enhanced the adsorption of LA on the catalyst surface, and both the Lewis and Br?nsted acidity associated with Nb2O5 and the metallic Cu0 sites promoted catalysis of the cascade hydrogenation, ring cyclization, ring-opening, and hydrogenation reactions to produce VA from LA. The bimetallic Nb-Cu/ZPS catalyst was also effective for the conversion of VA into various valeric esters in C1-C5 alcohol media. The presence of Nb2O5 effectively suppressed metal leaching and coke formation, which are serious issues in the liquid-phase conversion of highly acidic LA during the reaction. The catalyst could be used for up to five consecutive cycles with marginal loss of activity, even without catalyst re-activation.

Oxidation of secondary alcohols using solid-supported hypervalent iodine catalysts

It is shown how secondary alcohols are oxidized to provide the corresponding ketones by use of Oxone and solid-supported hypervalent iodine catalysts. Under experimentally simple conditions with acetonitrile at elevated temperatures, excellent conversions were achieved with low catalyst loadings (0.2-5 mol%) when employing the conjugates 5 and 6 derived from IBX and IBS. The catalysts are broadly applicable to a range of alcohol substrates. Of primary importance with respect to sustainability issues, the metal-free catalysts are easily removed from the reaction mixture through filtration, and they can be re-used in oxidation processes for multiple times, without loss of catalytic activity.

Nickel-catalyzed reductive defunctionalization of esters in the absence of an external reductant: Activation of C-O bonds

The nickel-catalyzed reductive cleavage of esters in the absence of an external reductant, which involves the cleavage of an inert acyl C-O bond in O-Alkyl esters is reported. Various groups, such as N-containing heterocycles, esters, amides, and even arene rings can function as a directing group.

Preparation method of 3,6,6-trimethyl-2,4-cycloheptadienone

The invention discloses a preparation method of 3,6,6-trimethyl-2,4-cycloheptadienone. The preparation method comprises the following steps: reacting 3-carene with O2 at 35 DEG C for 24 hours under the catalysis of CrO3-Al2O3 so as to generate a product I with a main component of 5-carone, wherein the conversion rate of 3-carene is about 81.3%, and the selectivity of 5-carone is 60.1%; reacting byvirtue of the product I at a pressure of 0-1kPa and temperature of 120 DEG C for 4 hours so as to convert the product I into a product II with a main component of 3,6,6-trimethyl-2,4-cycloheptadienone, wherein the conversion rate of 5-carone is about 100%, and the selectivity of 3,6,6-trimethyl-2,4-cycloheptadienone is 98.7%; and carrying out reduced pressure distillation on the product II, so asto obtain 3,6,6-trimethyl-2,4-cycloheptadienone, wherein the yield is more than 75%, and the purity is more than 95%.

Iminyl Radical-Triggered Intermolecular Distal C(sp3)-H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade

An efficient iron-catalyzed intermolecular remote C(sp3)-H heteroarylation of alkyl ketones has been developed via an iminyl radical-triggered 1,5-hydrogen-atom transfer (HAT) cascade. This protocol was amenable to a wide variety of alkyl ketones and heteroaryls, thus providing a straightforward method for the late-stage functionalization of alkylketones and heteroaryls.

Metal-Free catalyst for visible-light-induced oxidation of unactivated alcohols using Air/Oxygen as an oxidant

9-Fluorenone acts as a metal-free and additive-free photocatalyst for the selective oxidation of primary and secondary alcohols under visible light. With this photocatalyst, a plethora of alcohols such as aliphatic, heteroaromatic, aromatic, and alicyclic compounds has been converted to the corresponding carbonyl compounds using air/oxygen as an oxidant. In addition to these, several steroids have been oxidized to the corresponding carbonyl compounds. Detailed mechanistic studies have also been achieved to determine the role of the oxidant and the photocatalyst for this oxidation.