57069-90-6

Basic information

• Product Name: 3,7-dimethyloct-2-enal
• Synonyms: 3,7-dimethyloct-2-enal;3,7-Dimethyl-2-octenal;Einecs 260-539-4
• CAS NO: 57069-90-6
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.24932
• EINECS: 260-539-4
• Mol File: 57069-90-6.mol

Chemical Properties

• Boiling Point: 218.4°C at 760 mmHg
• Flash Point: 64.6°C
• Appearance: /
• Density: 0.835g/cm³
• Vapor Pressure: 0.126mmHg at 25°C
• Refractive Index: 1.437
• CAS DataBase Reference: 3,7-dimethyloct-2-enal(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7-dimethyloct-2-enal(57069-90-6)
• EPA Substance Registry System: 3,7-dimethyloct-2-enal(57069-90-6)

Safety Data

• Hazardous Substances Data: 57069-90-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h7-9H,4-6H2,1-3H3/b10-7-

Upstream product

• 40607-48-5 3,7-dimethyl-2-octen-1-ol 
• 18479-49-7 3,7-dimethyl-oct-1-en-3-ol 
• 775352-33-5 1,1-dimethoxy-3,7-dimethyl-octan-3-ol 
• 856576-48-2 acetic acid-(3,7-dimethyl-octa-1,2-dienyl ester) 
• 92371-74-9 1,1-diacetoxy-3,7-dimethyl-oct-2-ene 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 1666-13-3 diphenyl diselenide 
• 266683-56-1 2-bromo-1,1-dimethoxy-3,7-dimethyloctane 
• 68141-23-1 1,1-dimethoxy-3,7-dimethyloctane 
• 18201-30-4 1t-chloro-7-methyl-oct-1-en-3-one 
• 777952-41-7 1,1-dimethoxy-7-methyl-octan-3-one 
• 1604-26-8 hydrodehydrolinalool 
• 928-68-7 6-methylheptan-2-one 
• 60018-13-5 3,7-dimethyl-1-octanal 

Downstream Products

• 60018-13-5 3,7-dimethyl-1-octanal 
• 61447-95-8 2-Methyl-4-isohexylbenzaldehyd 
• 61447-90-3 6-Methyl-4,6-bis-(4-methyl-pentyl)-cyclohexa-1,3-dienecarbaldehyde 
• 61447-94-7 6-Methyl-4,6-bis-(4-methyl-pentyl)-cyclohexa-1,4-dienecarbaldehyde 
• 40607-48-5 3,7-dimethyl-2-octen-1-ol 

Relevant articles and documents

Organocatalyst-mediated dehydrogenation of aldehydes to α,β-unsaturated aldehydes, and oxidative and enantioselective reaction of aldehydes and nitromethane catalyzed by diphenylprolinol silyl ether

A one-pot transformation of aldehydes into α,β-unsaturated aldehydes was developed using both N-benzyl-N-methylamine and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as catalysts and MnO2 as a terminal oxidant. An oxidative and enantioselective reaction of aldehydes and nitromethane was established using both diphenylprolinol silyl ether and DDQ as a catalyst with MnO2 as a terminal oxidant, in which synthetically important β-substituted γ-nitro aldehydes were obtained with excellent enantioselectivity. Copyright

Alkaline modifiers as performance boosters in citral hydrogenation over supported ionic liquid catalysts (SILCAs)

Supported ionic liquid catalysts (SILCAs) consist of nano-scale catalytic species immobilized in an ionic liquid layer which, in turn, is immobilized on a solid support. In this work, novel SILCAs containing various inorganic alkaline modifiers (e.g. potassium hydroxide) were prepared and applied in citral hydrogenation reactions. The supported ionic liquid catalyst systems demonstrated enhanced reaction rates and improved selectivities toward citronellal in citral hydrogenation. With the addition of an alkaline modifier into ionic liquid layer, the catalyst selectivity increased from 16% to 74%. In fact, a highly selective reaction route toward citronellal was accomplished.

Application of a cross-linked Pd-chitosan catalyst in liquid-phase- hydrogenation using molecular hydrogen

Chitosan was cross-linked with hexamethylendiisocyanate and loaded with Pd which was subsequently reduced with NaBH4. The prepared catalyst was characterized by FT-IR and elemental analysis. The metal content was determined by ICP-MS measurements. Several substrates (cyclohex-2-enone, benzalacetophenone, 1,2-diphenylacetylene, and N-benzylidenaniline) were hydrogenated successfully in ethanol at mild conditions (50 °C, p(H 2) ～6 bar) utilizing a microwave reactor. Reaction parameters like temperature, hydrogen pressure, and the solvent were varied. It was shown that the reduction of the catalyst is crucial for catalytic activity. The catalyst was reused ten times for the hydrogenation of cyclohex-2-enone, without showing a dramatic loss in immobilized metal content. Also the polymeric support material did not show any decomposition.

Iron-iron oxide core-shell nanoparticles are active and magnetically recyclable olefin and alkyne hydrogenation catalysts in protic and aqueous media

We report for the first time the use of iron-iron oxide core-shell nanoparticles for the hydrogenation of olefins and alkynes under mild conditions in ethanol and in an aqueous medium. This catalyst proves robust towards the presence of oxidants, such as oxygen and water, is magnetically recoverable and shows selectivity towards the less activated double bonds. The Royal Society of Chemistry 2012.

Shape controlled synthesis of palladium nanocrystals by combination of oleylamine and alkylammonium alkylcarbamate and their catalytic activity

The shape of Pd nanocrystals (NCs) can be controlled by combination of oleylamine (OAm) and alkylammonium alkylcarbamate (AAAC), and Pd spheres, tetrahedra and multipods have been synthesized. The multipods and tetrahedra are much more active than the sph

Nature of catalyst deactivation during citral hydrogenation: A catalytic and ATR-IR study

Deactivation of a 5 wt% Pd/Al2O3 catalyst during hydrogenation of citral (1) to citronellal (2), 3,7-dimethyl-2-octenal (3), and dihydrocitronellal (4) has been studied in a continuous-flow fixed-bed reactor. The reactions were carried out at 40 °C and 190 bar in hexane, supercritical CO2, or ethane as solvents. ATR-IR spectroscopic analysis of the solid/liquid interphase under reaction conditions at low pressure revealed that 1 and 3 decarbonylate on the Pd surface resulting in strongly adsorbed CO and CxHy-type hydrocarbon fragments. The absence of decarbonylation products from 2 and 4 and the excellent chemoselectivity for the hydrogenation of the C=C bonds are interpreted by adsorption of the molecules in a tilted position on Pd, π-bonded via one C=C bond (2) or di-π-bonded via the C=C-C=O fragment (1 and 3). A practically important observation is that a short reoxidation by air of the used Pd/Al2O3 under very mild conditions (40 °C, 6 bar) can circumvent further deactivation, but the original activity cannot be regained. All these observations indicate that the irreversible deactivation of Pd/Al2O3 cannot be traced to CO poisoning. We propose that site blocking caused by heavier oligomeric surface products is the major reason for the observed catalyst deactivation. Elsevier Inc. All rights reserved.

Liquid-phase citral hydrogenation over SiO2-supported Group VIII metals

Citral hydrogenation was studied over SiO2-supported Group VIII metals at 300 K and 1 atm in the absence of all transport limitations as verified by the Madon-Boudart test and the Weisz-Prater criterion. The initial turnover frequency (TOF) for

Liquid-phase hydrogenation of citral over Pt/SiO2 catalysts - I. Temperature effects on activity and selectivity

Liquid-phase hydrogenation of citral (3,7-dimethyl-2,6-octadienal) over Pt/SiO2 catalysts was studied under kinetic conditions free of transport limitations and poisoning effects at 298-423 K and 7-21 atm. The rate of citral hydrogenation exhibited a minimum in activity between 298 and 423 K, and this was attributed to the relative activation energies for the decomposition of the unsaturated alcohol and desorption of CO. At low reaction temperatures (298 K), the rate of citral disappearance was low and CO was slowly accumulated under reaction conditions to block active sites and eventually led to a complete loss of activity. At 373 K, alcohol decomposition was more rapid, but the CO desorption rate was significantly enhanced and a pseudo-steady state was readily established which resulted in minimal additional inhibition and conventional Arrhenius behavior with an activation energy of 7 kcal/mole. The reaction kinetics for each hydrogenation reaction in the reaction network were modeled using a Langmuir-Hinshelwood model invoking dissociative adsorption of hydrogen, competitive adsorption between hydrogen and the reactive organic species, and the observed product distributions at each temperature were described very well. Furthermore, deactivation due to decomposition of the unsaturated alcohols geraniol and nerol, along with CO desorption at higher temperatures, was invoked to account for the unusual rate dependence on temperature.

Novel Preparation of α,β-Unsaturated Aldehydes. Benzeneselenolate Promotes Elimination of HBr from α-Bromoacetals

Acetalization, α-bromination, nucleophilic phenylselenenylation, oxidative elimination/hydrolysis was investigated as a novel protocol for the α,β-dehydrogenation of aldehydes. Treatment of acetals with bromine in methylene chloride afforded the corresponding α-bromoacetals in 80-90% yields. Nucleophilic phenylselenenylation was then conveniently effected by treatment with benzenese-lenolate generated in situ in dimethyl sulfoxide from diphenyl diselenide, hydrazine and potassium carbonate. Unbranched α-bromoacetals cleanly afforded substitution products whereas β- and γ-branched ones gave substantial amounts of α,β-unsaturated acetals via formal loss of hydrogen bromide. Oxidative elimination/hydrolysis of these mixtures afforded α,β-unsaturated aldehydes in 50-80% overall yields. In the case of tertiary α-bromoacetals, treatment with benzeneselenolate afforded only dehydrobromination products as mixtures of isomers. The presence of at least a catalytic amount of the organoselenium reagent was found to be crucial for olefin formation. A SET-mechanism, involving benzeneselenolate-induced electron transfer to the halide, loss of bromide ion, and hydrogen atom or proton/electron was proposed for the benzenselenolate-promoted elimination reaction. Experiments designed to trap carbon-centered radicals in intramolecular cyclization or ring-opening reactions failed to provide any evidence for free-radical intermediates.

AN EFFICIENT REAGENT FOR SYNTHESIS OF α,β-UNSATURATED ALDEHYDES 3-METHYLTHIO-2-PROPENYL p-TOLYL SULFONE

Alkylation of 3-methylthio-2-propenyl p-tolyl sulfone (1) with an alkyl halide and a base (NaH or KOH-TOMAC) took place at the position α to the sulfonyl group to give optionally a mono- or dialkylated product (2 or 3), which was converted to β-monosubstituted or β,β-disubstituted α,β-unsaturated aldehyde (6 or 7), respectively, by TiCl4-assisted hydrolysis followed by the removal of p-toluenesulfinic acid.