931-57-7

Basic information

• Product Name: 1-METHOXYCYCLOHEXENE
• Synonyms: 1-Cyclohexen-1-yl methyl ether;1-Cyclohexen-1-ylmethylether;1-Methoxy-1-cyclohexene;1-methoxy-cyclohexen;Cyclohexanone methyl enol ether;Cyclohexene,1-methoxy-;Ether, 1-cyclohexen-1-yl methyl;Ether,1-cyclohexen-1-ylmethyl
• CAS NO: 931-57-7
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.17
• Product Categories: Miscellaneous Reagents
• Mol File: 931-57-7.mol

Chemical Properties

• Boiling Point: 165.3 °C at 760 mmHg
• Flash Point: 44.7 °C
• Appearance: Colourless oil
• Density: 0.89 g/cm³
• Vapor Pressure: 2.48mmHg at 25°C
• Refractive Index: 1.453
• Solubility: Methanol
• CAS DataBase Reference: 1-METHOXYCYCLOHEXENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHOXYCYCLOHEXENE(931-57-7)
• EPA Substance Registry System: 1-METHOXYCYCLOHEXENE(931-57-7)

Safety Data

• Hazardous Substances Data: 931-57-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-METHOXYCYCLOHEXENE is used as a reactive intermediate for the synthesis of various organic compounds. Its presence in the molecule allows for a range of chemical reactions to take place, facilitating the creation of new compounds with different properties and applications.
Used in the Production of 1-Chloro-1-Methoxycyclohexane:
In the chemical industry, 1-METHOXYCYCLOHEXENE is used as a precursor to produce 1-chloro-1-methoxycyclohexane. This is achieved through its reaction with hydrochloric acid, which adds a chlorine atom to the molecule, creating a new compound with potential applications in various fields.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 3396, 1985 DOI: 10.1021/jo00218a030Tetrahedron Letters, 23, p. 631, 1982 DOI: 10.1016/S0040-4039(00)86908-7

InChI:InChI=1/C7H12O/c1-8-7-5-3-2-4-6-7/h5H,2-4,6H2,1H3

Upstream product

• 91-22-5 quinoline 
• 933-40-4 cycloxexanone dimethyl ketal 
• 98-88-4 benzoyl chloride 
• 2161-90-2 1-methoxy-1,3-cyclohexadiene 
• 37567-78-5 1,5-dimethoxy-1,4-cyclohexadiene 
• 74-83-9 methyl bromide 
• 155069-25-3 cyclohexanone enolate 
• 67-56-1 methanol 
• 108-94-1 cyclohexanone 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 2886-59-1 1-methoxycyclohexa-1,4-diene 
• 39000-58-3 1,4-dimethoxycyclohexa-1,4-diene 
• 100-66-3 methoxybenzene 

Downstream Products

• 31236-56-3 (2,2-Dimethoxy-cyclohexyl)-carbamic acid 2,2,2-trichloro-ethyl ester 
• 31236-57-4 (2,2-Dimethoxy-cyclohexyl)-carbamic acid benzyl ester 
• 67820-35-3 2-methoxycyclohexanone dimethyl acetal 
• 17578-82-4 N-(2-oxocyclohexyl)acetamide 
• 3297-69-6 2-[4]pyridyl-cyclohexanone 
• 115444-30-9 3-(pyridin-4-yl)cyclohexan-1-one 
• 133377-50-1 2-Heptadecafluorooctyl-1,1-dimethoxy-cyclohexane 
• 63703-34-4 2,2-dimethoxycyclohexanol 
• 1728-17-2 α-bromocyclohexanone dimethyl ketal 
• 95349-80-7 2-(1'-methyl-2'-p-tolylthio-1'-methoxyethyl)cyclohexan-1-one 
• 107197-50-2 2-(penta-2,4-dienyl)cyclohexanone 
• 93719-18-7 3-hydroxy-2-(cyclohex-1'-enyl)-5,5-dimethylcyclohex-2-enone 
• 118668-59-0 2-Bromo-1-methoxy-1-prop-2-ynyloxy-cyclohexane 
• 415679-41-3 (R)-2-hydroxy-1,1-dimethoxycyclohexane 

Relevant articles and documents

Alkylation of Enolate Ions

We describe a procedure for studying gas-phase ion-molecule chemistry in which the neutral reaction products are collected and identified.Our experiment uses a flowing afterglow device configured with a cryogenic trapping column; material collected on this column is separated by capillary chromatography and the individual components are identified by their retention time and their electron impact mass spectrum.We have used this device to study the reaction of the cyclohexanone enolate ion with CH3Br.We find that reaction of this enolate proceeds with a rate constant of 3.9*10-10 cm3 molecule-1 s-1 to produce only the product resulting from O-alkylation, 1-methoxycyclohexene; there is no evidence for the product resulting from C-alkylation.

Catalytic role of metals supported on SBA-16 in hydrodeoxygenation of chemical compounds derived from biomass processing

Hydrodeoxygenation (HDO) carried out at high temperatures and high hydrogen pressures is one of the alternative methods of upgrading pyrolytic oils from biomass, leading to high quality biofuels. To save energy, it is important to carry out catalytic proc

Ruthenium-containing SBA-12 catalysts for anisole hydrodeoxygenation

Hexagonally ordered mesoporous silica SBA-12 catalysts containing various amounts of Ru (1 or 3 wt.percent) were obtained by wet impregnation. These catalysts were thoroughly characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM)

The effect of metal (Nb, Ru, Pd, Pt) supported on SBA-16 on the hydrodeoxygenation reaction of phenol

Ordered silica materials of SBA-16 type were synthesized, characterized as to their physicochemical properties and used as supports of the active phases which were niobium, ruthenium, palladium or platinum ions. Physicochemical properties of the systems o

Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds

Palladium on carbon catalyzes C?O bond cleavage of aryl ethers (diphenyl ether and cyclohexyl phenyl ether) by alcohols (R?OH) in H2. The aromatic C?O bond is cleaved by reductive solvolysis, which is initiated by Pd-catalyzed partial hydrogenation of one phenyl ring to form an enol ether. The enol ether reacts rapidly with alcohols to form a ketal, which generates 1-cyclohexenyl?O?R by eliminating phenol or an alkanol. Subsequent hydrogenation leads to cyclohexyl?O?R.

Mechanistic Studies on the Base-Promoted Conversion of Alkoxy-Substituted, Ring-Fused gem-Dihalocyclopropanes into Furans: Evidence for a Process Involving Electrocyclic Ring Closure of a Carbonyl Ylide Intermediate

The mechanism associated with the base-promoted conversion of alkoxy-substituted and ring-fused gem-dihalocyclopropanes such as 40 into annulated furans has been explored. Treatment of compound 40 with potassium tert-butoxide affords a mixture of furans 23/27 and 41, an outcome that suggests the intermediacy of the slowly interconverting carbonyl ylides 42 and 43 that undergo rapid [1,5]-electrocyclizations and subsequent dehydrohalogenation to afford the observed products. This proposal is supported by ab initio MO and DFT calculations that also suggest a vinylcarbene insertion pathway is less likely to be operative.

Synthesis of acid-sensitive connection unit and its use in DNA sequencing

The invention discloses a synthesis method of an acid sensitive connection unit, and a use of the acid sensitive connection unit in DNA sequencing. The structural formula of the acid sensitive connection unit is shown in the specification. In the structural formula, R is NH2 or N3, m is an integer from 0 to 44, and n is an integer from 0 to 44; R1 and R2 respectively represent an aliphatic alkyl group, or R1 and R2 respectively represent an aromatic derivative, or R1 is a phenyl group, a naphthyl group, a phenyl derivative or a naphthyl derivative, and R2 is an aliphatic alkyl group or hydrogen; or R2 is a phenyl group, naphthyl group, a phenyl derivative or a naphthyl derivative, R1 is an aliphatic alkyl group or hydrogen, or R1 and R2 form a cyclohexyl group, a cyclopentyl group or a cyclobutyl group. A reversible terminal obtained through connecting the acid sensitive connection unit with nucleotide and fluorescein can be used in DNA sequencing-by-synthesis. The reversible terminal can be used in the DNA sequencing; and raw materials required by the synthesis method are simple and can be easily obtained, and the synthesis process is a routine chemical reaction, so the method can realize large scale popularization use.

A Lamellar Coordination Polymer with Remarkable Catalytic Activity

A positively charged lamellar coordination polymer based on a flexible triphosphonic acid linker is reported. [Gd(H4nmp)(H2O)2]Cl?2 H2O (1) [H6nmp=nitrilotris(methylenephosphonic acid)] was obtained by a one-pot approach by using water as a green solvent and by forcing the inclusion of additional acid sites by employing HCl in the synthesis. Compound 1 acts as a versatile heterogeneous acid catalyst with outstanding activity in organic reactions such as alcoholysis of styrene oxide, acetalization of benzaldehyde and cyclohexanaldehyde and ketalization of cyclohexanone. For all reaction systems, very high conversions were reached (92–97 %) in only 15–30 min under mild conditions (35 °C, atmospheric pressure). The coordination polymer exhibits a protonic conductivity of 1.23×10?5S cm?1at 98 % relative humidity and 40 °C.

Pt nanoparticle supported on nanocrystalline CeO2: Highly selective catalyst for upgradation of phenolic derivatives present in bio-oil

Pt nanoparticle supported on nanocrystalline CeO2 was prepared, and it was found that the catalyst can selectively hydrogenate phenolic derivatives present in bio-oil. The catalyst was characterized by XRD, XPS, ICP-AES, EXAFS, SEM and TEM. TEM micrograms confirm the presence of very small Pt nanoparticles supported on nanocrystalline CeO2. The catalyst was found to be very effective in liquid phase hydrogenation of phenol and phenolic compounds present in bio-oil in the presence of molecular H2. The synergy between the surface and very small Pt particles on the nanocrystalline CeO2 plays the most vital role towards the extremely high catalytic activity of the catalyst. The reusability of the catalyst was tested, and it was found that the catalyst does not exhibit any significant change in its catalytic activity even after five reuses. The catalyst showed ～100% conversion with very high selectivity after 3 h in phenol conversions of 100% with >98% cyclohexanol selectivity achieved after 3 h of reaction at 100 °C in aqueous medium.

Synthesis, characterization, and biocompatibility of biodegradable hyperbranched polyglycerols from acid-cleavable ketal group functionalized initiators

Herein we report the synthesis of biodegradable hyperbranched polyglycerols (BHPGs) having acid-cleavable core structure by anionic ring-opening multibranching polymerization (ROMBP) of glycidol using initiators bearing dimethyl and cyclohexyl ketal groups. Five different multifunctional initiators carrying one to four ketal groups and two to four hydroxyl groups per molecule were synthesized. The hydroxyl carrying initiators containing one ketal group per molecule were synthesized from ethylene glycol. An alkyne-azide click reaction was used for synthesizing initiators containing multiple cyclohexyl ketal linkages and hydroxyl groups. The synthesized BHPGs exhibited monomodal molecular weight distributions and polydispersity in the range of 1.2 to 1.6, indicating the controlled nature of the polymerizations. The polymers were relatively stable at physiological pH but degraded at acidic pH values. The polymer degradation was dependent on the type of ketal structure present in the BHPG; polymers with cyclohexyl ketal groups degraded at much slower rates than those with dimethyl ketal groups at a given pH. Good control of polymer degradation was achieved under mild acidic conditions by changing the structure of ketal linkages. A precise control of the molecular weight of the degraded HPG was achieved by controlling the number of ketal groups within the core, as revealed from the gel permeation chromatography (GPC) analyses. The decrease in the polymer molecular weights upon degradation was correlated well with the number of ketal groups in their core structure. Our data support the suggestion that glycidol was polymerized uniformly from all hydroxyl groups of the initiators. BHPGs and their degradation products were highly biocompatible, as measured by blood coagulation, complement activation, platelet activation, and cell viability assays. The controlled degradation profiles of these polymers together with their excellent biocompatibility make them suitable for drug delivery and bioconjugation applications.