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1-Propenylcyclohexane, also known as cyclohexanepropene, is an organic compound with the molecular formula C9H16. It is a colorless liquid that is insoluble in water but soluble in organic solvents. 1-Propenylcyclohexane consists of a cyclohexane ring with a propenyl group (a three-carbon chain with a double bond) attached to one of its carbon atoms. 1-Propenylcyclohexane is used as a chemical intermediate in the synthesis of various organic compounds, such as fragrances, pharmaceuticals, and agrochemicals. It is also employed as a solvent and a reagent in various chemical reactions. Due to its flammable and reactive nature, it requires proper handling and storage to prevent accidents and environmental contamination.

5364-83-0

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5364-83-0 Usage

Physical state

Colorless liquid

Odor

Fruity

Uses

Flavor and fragrance ingredient in food and cosmetics, production of polymers and plastics

Environmental impact

Volatile organic compound, potential air pollutant

Occurrence

Synthetic, not found naturally in significant amounts

Safety

Flammable, requires careful handling and storage

Check Digit Verification of cas no

The CAS Registry Mumber 5364-83-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,6 and 4 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5364-83:
(6*5)+(5*3)+(4*6)+(3*4)+(2*8)+(1*3)=100
100 % 10 = 0
So 5364-83-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H16/c1-2-6-9-7-4-3-5-8-9/h2,6,9H,3-5,7-8H2,1H3

5364-83-0Relevant articles and documents

METHODS OF BORYLATION AND USES THEREOF

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Page/Page column 61-62, (2021/04/30)

The present invention relates, in general terms, to methods of borylation and uses thereof. In particular, the present invention provides a method of borylating an alkene compound by contacting the compound with a boron compound, a Fe pre-catalyst and a protic additive. The borylation occurs at a vicinal (β) position to an electron donating or electron withdrawing moiety of the compound.

Visible-Light Controlled Divergent Catalysis Using a Bench-Stable Cobalt(I) Hydride Complex

Beltran, Frédéric,Bergamaschi, Enrico,Teskey, Christopher J.

supporting information, p. 5180 - 5184 (2020/04/22)

While the use of visible light in conjunction with transition metal catalysis offers powerful opportunities to switch between on/-off states of catalytic activity, the next frontier would be the ability to switch the actual function of the catalyst and resulting products. Here we report such an example of multi-dimensional catalysis. Featuring an easily prepared, bench-stable cobalt(I) hydride complex in conjunction with pinacolborane, we can switch the reaction outcome between two widely employed transformations, olefin migration and hydroboration, with visible light as the trigger.

Iron-Catalyzed Tunable and Site-Selective Olefin Transposition

Yu, Xiaolong,Zhao, Haonan,Li, Ping,Koh, Ming Joo

supporting information, p. 18223 - 18230 (2020/12/04)

The catalytic isomerization of C-C double bonds is an indispensable chemical transformation used to deliver higher-value analogues and has important utility in the chemical industry. Notwithstanding the advances reported in this field, there is compelling demand for a general catalytic solution that enables precise control of the C═C bond migration position, in both cyclic and acyclic systems, to furnish disubstituted and trisubstituted alkenes. Here, we show that catalytic amounts of an appropriate earth-abundant iron-based complex, a base and a boryl compound, promote efficient and controllable alkene transposition. Mechanistic investigations reveal that these processes likely involve in situ formation of an iron-hydride species which promotes olefin isomerization through sequential olefin insertion/β-hydride elimination. Through this strategy, regiodivergent access to different products from one substrate can be facilitated, isomeric olefin mixtures commonly found in petroleum-derived feedstock can be transformed to a single alkene product, and unsaturated moieties embedded within linear and heterocyclic biologically active entities can be obtained.

Double-Bond Isomerization: Highly Reactive Nickel Catalyst Applied in the Synthesis of the Pheromone (9 Z,12 Z)-Tetradeca-9,12-dienyl Acetate

Weber, Felicia,Schmidt, Anastasia,R?se, Philipp,Fischer, Michel,Burghaus, Olaf,Hilt, Gerhard

supporting information, p. 2952 - 2955 (2015/06/30)

A highly reactive nickel catalyst comprising NiCl2(dppp) or NiCl2(dppe) with zinc powder, ZnI2 and Ph2PH, was applied in the isomerization of terminal alkenes to Z-2-alkenes. The double-bond geometry of the 2-alkene can be controlled via the reaction temperature to yield the 2-Z-alkenes in excellent yields and high Z-selectivities. The formation of other constitutional isomers, such as 3-alkenes, is suppressed on the basis of the proposed mechanism via a 1,2-hydride shift from the metal to the Ph2P ligand. The nickel-catalyzed isomerization reaction was then applied in the synthesis of (9Z,12Z)-tetradeca-9,12-dienyl acetate, a pheromone with a 2Z,5Z-diene subunit.

An alternative mechanism for the cobalt-catalyzed isomerization of terminal alkenes to (Z)-2-alkenes

Schmidt, Anastasia,N??dling, Alexander R.,Hilt, Gerhard

supporting information, p. 801 - 804 (2015/03/04)

The cobalt-catalyzed selective isomerization of terminal alkenes to the thermodynamically less-stable (Z)-2-alkenes at ambient temperatures takes place by a new mechanism involving the transfer of a hydrogen atom from a Ph2PH ligand to the starting material and the formation of a phosphenium complex, which recycles the Ph2PH complex through a 1,2-H shift.

Kinetic resolution of 1,2-diols through highly site- and enantioselective catalytic silylation

Zhao, Yu,Mitra, Aurpon W.,Hoveyda, Amir H.,Snapper, Marc L.

, p. 8471 - 8474 (2008/09/18)

(Chemical Equation Presented) Resolved to silylate: A chiral silylation catalyst is used for kinetic resolution of three classes of acyclic 1,2-diols. The catalyst differentiates, with excellent precision, between the two hydroxy groups of a substrate. The majority of the diols, obtained in high enantiomeric purity, cannot be accessed with similar stereochemical purity through catalytic asymmetric dihydroxylation.

Phosphabarrelenes as ligands in rhodium-catalyzed hydroformylation of internal alkenes essentially free of alkene isomerization

Fuchs, Evelyn,Keller, Manfred,Breit, Bernhard

, p. 6930 - 6939 (2007/10/03)

Despite significant research efforts in the past, one of the remaining problems to be solved in industrially important hydroformylation is the chemoselective low-pressure hydroformylation of internal alkenes. We report here on a new class of phosphabarrelene/rhodium catalysts 2 that display very high activity towards hydroformylation of internal alkenes with an unusually low tendency towards alkene isomerization. Preparation of new phosphabarrelene ligands, studies of their coordination properties, as well as results obtained in the rhodium-catalyzed hydroformylation of cyclic and acyclic internal alkenes are reported.

Palladium-catalyzed asymmetric silaboration of allenes

Ohmura, Toshimichi,Taniguchi, Hiroki,Suginome, Michinori

, p. 13682 - 13683 (2007/10/03)

An enantioselective silaboration of allenes was achieved using an achiral silylborane in the presence of a palladium catalyst bearing a chiral monodentate phosphine ligand. (R)-2-Bis(3,5-dimethylphenyl)phosphino-1,1-binaphthyl gave the highest enantiosele

Diastereoselective free radical halogenation, azidation, and rearrangement of β-silyl Barton esters

Masterson, Douglas S.,Porter, Ned A.

, p. 4253 - 4256 (2007/10/03)

(equation presented) Barton esters of β-silylcarboxylic acids were decomposed by photolysis alone in organic solvents or in the presence of ethanesulfonyl azide or bromotrichloromethane. Products of the reaction, β-silylthiopyridyl ethers, β-silyl azides, or alkenes, were formed with significant control of stereochemistry.

Preferential catalytic hydrogenation of aromatic compounds versus ketones with a palladium substituted polyoxometalate as pre-catalyst

Kogan, Vladimir,Aizenshtat, Zeev,Neumann, Ronny

, p. 272 - 274 (2007/10/03)

A palladium-substituted polyoxometalate having a Keggin structure, supported on γ-alumina or active carbon, was used as a catalyst precursor for catalytic hydrogenation. The catalyst system enabled fast hydrogenation of arenes at 30 bar H2 and 230°C. Most interesting was the finding that arenes could be selectively reduced in the presence of distal ketone groups under similar conditions, 30 bar H2 and 200°C. For example, 1-phenyl-2-propanone yielded 1-cyclohexyl-2-propanone with no reduction of the ketone moiety. Additionally, aromatic compounds with vicinal (conjugated) ketone moieties underwent complete hydrogenation to saturated hydrocarbons and catalytic McMurry coupling was observed for aliphatic aldehydes.

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