2816-57-1

Basic information

• Product Name: 2,5-DIMETHYLCYCLOHEXANONE
• Synonyms: 2,6-Dimethylcyclohexanone cis + trans;2,6-Dimethylcyclohexanone,c&t;2,5-DIMETHYLCYCLOHEXANONE;2,6-DIMETHYLCYCLOHEXANONE;2,6-Dimethylcyclohexanone, mixture of isomers;2,6-dimethylcyclohexan-1-one;2,6-DIMETHYLCYCLOHEXANONE, 98%, MIXTUREOF ISOMERS;2,6-dimethylcyclohexanon
• CAS NO: 2816-57-1
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.2
• EINECS: 220-570-6
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 2816-57-1.mol

Chemical Properties

• Melting Point: 9.25°C (estimate)
• Boiling Point: 174-176 °C(lit.)
• Flash Point: 124 °F
• Appearance: /
• Density: 0.925 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.07mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Storage Temp.: Flammables area
• BRN: 1099000
• CAS DataBase Reference: 2,5-DIMETHYLCYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHYLCYCLOHEXANONE(2816-57-1)
• EPA Substance Registry System: 2,5-DIMETHYLCYCLOHEXANONE(2816-57-1)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2816-57-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Dimethylcyclohexanone is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
2,5-Dimethylcyclohexanone serves as a valuable building block in the synthesis of a wide range of organic compounds, including fragrances, flavors, and other specialty chemicals. Its reactivity and versatility make it a popular choice for chemists working on the development of new molecules with specific properties.
Used in Research and Development:
Due to its unique chemical properties, 2,5-dimethylcyclohexanone is often utilized in research and development settings to study various chemical reactions and processes. It can be used to investigate the effects of structural modifications on the properties and reactivity of cyclohexanone derivatives.
Used in Analytical Chemistry:
2,5-Dimethylcyclohexanone can be employed as a reference compound or a standard in analytical chemistry for the calibration of instruments and the development of new analytical methods. Its distinct chemical properties make it suitable for these applications.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 1341, 1983 DOI: 10.1016/S0040-4039(00)81651-2

InChI:InChI=1/C8H14O/c1-6-4-3-5-7(2)8(6)9/h6-7H,3-5H2,1-2H3/t6-,7-/m0/s1

Upstream product

• 583-60-8 2-Methylcyclohexanone 
• 74-88-4 methyl iodide 
• 19980-35-9 1-trimethylsilyloxy-2-methyl-1-cyclohexene 
• 63547-53-5 2,6-dimethyl-1-(trimethylsiloxy)cyclohexene 
• 7647-01-0 hydrogenchloride 
• 859069-07-1 1,5-dimethyl-2,4-diphenyl-3-oxa-bicyclo[3.3.1]nonan-9-one 
• 1194-91-8 3-methyl-2-oxo-cyclohexanecarbaldehyde 
• 5337-72-4 2,6-dimethylcyclohexanol 
• 7722-84-1 dihydrogen peroxide 
• 81-20-9 2,6-dimethylnitrobenzene 
• 576-26-1 2.6-dimethylphenol 
• 638-04-0 1,3-dimethylcyclohexane 
• 67-56-1 methanol 
• 108-94-1 cyclohexanone 

Downstream Products

• 56021-69-3 4-(2,6-dimethyl-cyclohex-1-enyl)-morpholine 
• 13756-99-5 2-Dimethylaminomethyl-2,6-dimethyl-cyclohexanon 
• 58898-13-8 2-(dibromomethylene)-1,3-dimethylcyclohexane 
• 61259-60-7 2,6-Dimethyl-2-n-octylcyclohexanon 
• 57387-81-2 E-Diethyl-(vinyloxy)-boran 
• 63048-81-7 5,9-Dimethyl-1-phenylthio-spiro<3.5>non-1-en 
• 99249-77-1 1-(2-Methyl-4-ethyl-phenethyl)-2,6-dimethyl-cyclohexanol 
• 94760-70-0 1-(2-Methyl-4-isopropyl-phenethyl)-2,6-dimethyl-cyclohexanol 
• 18707-85-2 2,6-Dimethyl-1-phenyl-cyclohexanol 
• 2570-68-5 6-oxo-2-methyl-heptanoic acid 
• 13652-33-0 2,6-Dimethyl-cyclohexylideneamine 
• 6203-90-3 1-Chlor-2.6-dimethyl-cyclohexen-⁽¹⁾ 
• 143143-52-6 1-(1-Azetidinyl)-2,6-dimethyl-1-cyclohexen 
• 138663-43-1 2,6-dimethyl-1-(3'-methyl-5'-phenylisoxazol-4'-yl)cyclohexan-1-ol 

Relevant articles and documents

H2O2 oxidation by Ce(IV) contained Weakley-type heteropolyoxometalate for various alcohols

Catalytic activity of Ce(IV) contained Weakley-type heteropolyoxometalate for the H2O2 oxidation of primary and secondary alcohols was evaluated for the first time. It was found that this catalyst exhibited a mild and thus quite selective activity, especially for benzylalcohols.

Progress toward the Synthesis of garsubellin A and related phloroglucins: the direct diastereoselective synthesis of the bicyclo[3.3.1]nonane core.

[reaction: see text] A highly diastereoselective single-step cyclization reaction provides access to the bicyclo[3.3.1]nonane core of the polyprenylated phloroglucin natural product garsubellin A. Further elaboration to a more functionalized analogue involves a sequential Claisen rearrangement/Grubbs olefin cross-metathesis strategy. Additionally, this strategy was extended to the preparation of the bis-quaternary carbon array found at the bridgehead positions of the phloroglucin natural products.

Rhenium(I)-Catalyzed C-Methylation of Ketones, Indoles, and Arylacetonitriles Using Methanol

A ReCl(CO)5/MeC(CH2PPh2)3 (L2) system was developed for the C-methylation reactions utilizing methanol and base, following the borrowing hydrogen strategy. Diverse ketones, indoles, and arylacetonitriles underwent mono-and dimethylation selectively up to 99% yield. Remarkably, tandem multiple methylations were also achieved by employing this catalytic system.

Increasing the steric hindrance around the catalytic core of a self-assembled imine-based non-heme iron catalyst for C-H oxidation

Sterically hindered imine-based non-heme complexes4and5rapidly self-assemble in acetonitrile at 25 °C, when the corresponding building blocks are added in solution in the proper ratios. Such complexes are investigated as catalysts for the H2O2oxidation of a series of substrates in order to ascertain the role and the importance of the ligand steric hindrance on the action of the catalytic core1, previously shown to be an efficient catalyst for aliphatic and aromatic C-H bond oxidation. The study reveals a modest dependence of the output of the oxidation reactions on the presence of bulky substituents in the backbone of the catalyst, both in terms of activity and selectivity. This result supports a previously hypothesized catalytic mechanism, which is based on the hemi-lability of the metal complex. In the active form of the catalyst, one of the pyridine arms temporarily leaves the iron centre, freeing up a lot of room for the access of the substrate.

A New Route to Cyclohexanone using H2CO3 as a Molecular Catalytic Ligand to Boost the Thorough Hydrogenation of Nitroarenes over Pd Nanocatalysts

Carbon dioxide has been important in green chemistry, especially in catalytic and chemical engineering applications. While exploring CO2 to produce cyclohexanone for nylon or nylon 66 that is currently produced with low yields using harsh catalytic methods, we made the exciting discovery that carbonic acid, generated from dissolved CO2 in water, was utilized as molecular catalytic ligand to produce cyclohexanone via the hydrogenation of nitrobenzene in aqueous solution that uses Pd catalysts with a total yield higher than 90 %. Importantly, the gaseous nature of catalytic ligand H2CO3 profoundly simplifies post-catalysis cleanup unlike liquid or solid catalysts. This new green catalysis strategy demonstrated the universality for hydrogenation of aromatic compounds like aniline and N-methylaniline and could be broadly applicable in other catalytic field like artificial photosynthesis and electrocatalytic organic synthesis.

α-Methylation of Ketones with Methanol Catalyzed by Ni/SiO2-Al2O3

α-Methylation of ketones with methanol catalyzed by a cheap and easy to handle Ni/SiO2-Al2O3 was explored. After optimization of the reaction between propiophenone and methanol, the desired product was obtained in 95 % isolated yield. A wide range of ketones was methylated under the optimized conditions (16 examples). This procedure was extended to a three-component cross-benzylation-methylation of acetophenone.

Ductile Pd-Catalysed Hydrodearomatization of Phenol-Containing Bio-Oils Into Either Ketones or Alcohols using PMHS and H2O as Hydrogen Source

A series of phenolic bio-oil components were selectively hydrodearomatized by palladium on carbon into the corresponding ketones or alcohols in excellent yields using polymethylhydrosiloxane and water as reducing agent. The selectivity of the reaction was governed by the water concentration where selectivity to alcohol was favoured at higher water concentrations. As phenolic bio-oil examples cardanol and beech wood tar creosote were studied as substrate to the developed reaction conditions. Cardanol was hydrodearomatized into 3-pentadecylcyclohexanone in excellent yield. From beech wood tar creosote, a mixture of cyclohexanols was produced. No hydrodeoxygenation occurred, suggesting the applicability of the reported method for the production of ketone-alcohol oil from biomass. (Figure presented.).

C -Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts

A versatile, selective, and recyclable heterogeneous catalytic method for the methylation of C-H bonds in alcohols, ketones, and indoles with methanol under oxidant-free conditions using a Pt-loaded carbon (Pt/C) catalyst in the presence of NaOH is reported. This catalytic system is effective for various methylation reactions: (1) the β-methylation of primary alcohols, including aryl, aliphatic, and heterocyclic alcohols, (2) the α-methylation of ketones, and (3) the selective C3-methylation of indoles. The reactions are driven by a borrowing-hydrogen mechanism. The reaction begins with the dehydrogenation of the alcohol(s) to afford aldehydes, which subsequently undergo a condensation reaction with the nucleophile (aldehyde, ketone, or indole), followed by hydrogenation of the condensation product by Pt-H species to yield the desired product. In all of the methylation reactions explored in this study, the Pt/C catalyst exhibits a significantly higher turnover number than other previously reported homogeneous catalytic systems. Moreover, it is demonstrated that the high catalytic activity of Pt can be rationalized in terms of the adsorption energy of hydrogen on the metal surface, as revealed by density functional theory calculations on different metal surfaces.

Syndiotactic Poly(aminostyrene)-Supported Palladium Catalyst for Ketone Methylation with Methanol

Palladium nanoparticles immobilized on an amino-functionalized syndiotactic polystyrene (sPS-N) served as a novel recyclable catalyst for the dimethylation and cross methyl alkylation of a wide range of ketones with methanol as the methylation agent. This heterogeneous catalyst (Pd@sPS-N) was highly robust and showed excellent thermal stability and chemical resistance. It not only showed remarkably high activity, but it could also be easily recovered by filtration without loss of activity.

Utilization of MeOH as a C1 Building Block in Tandem Three-Component Coupling Reaction

Ru(II) catalyzed tandem synthesis of α-branched methylated ketones via multicomponent reactions following the hydrogen borrowing process is described. This nonphosphine-based air and moisture stable catalyst efficiently produced various methylated ketones using methanol as a methylating agent. This system was found to be highly effective in three-component coupling between methanol, primary alcohols, and methyl ketones. A proposed catalytic cycle for the α-methylation is supported by DFT calculations as well as kinetic experiments.