17627-49-5

Basic information

• Product Name: Menthone
• Synonyms: 5-Methyl-2-(1-methylethyl)cyclohexanone, trans-; AI3-11106; CCRIS 5747; Cyclohexan-1-one, 2-isopropyl-5-methyl-, racemic; Cyclohexanone, 5-methyl-2-(1-methylethyl)-, trans-; FEMA No. 2667; HSDB 1268; Menthone (natural); Menthone racemic; Neomenthone; p-Menthan-3-one racemic; p-Menthan-3-one, trans-; p-Menthone; trans-Menthan-3-one; (dl)-Menthone; Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)-rel-; Cyclohexanone, 5-methyl-2-(1-methylethyl)-, trans-(+/-)-; p-Menthan-3-one, dl-; trans-Menthone; (2R,5S)-5-methyl-2-(propan-2-yl)cyclohexanone
• CAS NO: 17627-49-5
• Molecular Formula: C10H18O
• Molecular Weight: 154.24932
• EINECS: 201-941-1
• Mol File: 17627-49-5.mol

Chemical Properties

• Boiling Point: 205°C at 760 mmHg
• Flash Point: 72.8°C
• Appearance: /
• Density: 0.881g/cm³
• Vapor Pressure: 0.256mmHg at 25°C
• Refractive Index: 1.442
• CAS DataBase Reference: Menthone(CAS DataBase Reference)
• NIST Chemistry Reference: Menthone(17627-49-5)
• EPA Substance Registry System: Menthone(17627-49-5)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:; R36:; R43:; R52/53:
• Safety Statements: S26:; S36/37:; S61:
• Hazardous Substances Data: 17627-49-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m0/s1

Upstream product

• 67-56-1 methanol 
• 2385-77-5 (R)-Citronellal 
• 89-83-8 thymol 
• 10458-14-7 (2R,5S)-menthone 
• 89-78-1 menthol 
• 38462-22-5 2-(1-mercapto-1-methylethyl)-5-methylcyclohexanone 
• 7647-01-0 hydrogenchloride 
• 4184-02-5 3,4-epoxy-p-menthane 
• 71-23-8 propan-1-ol 
• 123-51-3 i-Amyl alcohol 
• 71-36-3 butan-1-ol 
• 80040-96-6 (+/-)-p-menth-4-en-3-one oxime 
• 89-82-7 pulegone 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 

Downstream Products

• 102608-96-8 2-benzylidene-6-isopropyl-3-methyl-cyclohexanone 
• 872266-49-4 (3-hydroxy-p-menthan-3-yl)-acetic acid 
• 35413-44-6 benzoic acid p-menth-3-en-3-yl ester 
• 33651-16-0 2-isopropyl-5-methyl-1-phenylethynyl-cyclohexanol 
• 38618-25-6 2-Isopropyl-1,5-dimethyl-cyclohexanol 
• 38618-20-1 1-Allyl-2-isopropyl-5-methyl-cyclohexanol 
• 28745-06-4 3-methyl-6-isopropyl-2-oxymethylenecyclohexanone 
• 18368-90-6 2-Isopropyl-5-methyl-1-phenyl-cyclohexanol 
• 54324-04-8 (2-hydroxy-p-menthan-2-yl)-acetic acid ethyl ester 
• 619-52-3 (1R)-menth-3-ene 
• 26127-89-9 ((1S,2R,5S)-1-Hydroxy-2-isopropyl-5-methyl-cyclohexyl)-acetic acid tert-butyl ester 
• 50281-16-8 (1R,4S)-1-isopropyl-4-methyl-2-methylenecyclohexane 
• 18427-47-9 2,6-Dibromo-2-isopropyl-5-methylcyclohexanone 

Relevant articles and documents

O3/Pb(OAc)4: a new and efficient system for the oxidative cleavage of allyl alcohols

Allyl alcohols undergo oxidative cleavage, affording the corresponding carbonyl compounds in good yields, when treated with ozone-lead(IV) acetate under mild conditions.

Origin of High Diastereoselectivity in Reactions of Seven-Membered-Ring Enolates

Unlike many reactions of their six-membered-ring counterparts, the reactions of chiral seven-membered-ring enolates are highly diastereoselective. Diastereoselectivity was observed for a range of substrates, including lactam, lactone, and cyclic ketone derivatives. The stereoselectivity arises from torsional and steric interactions that develop when electrophiles approach the diastereotopic π-faces of the enolates, which are distinguished by subtle differences in the orientation of nearby atoms of the ring.

A Mild, General, Metal-Free Method for Desulfurization of Thiols and Disulfides Induced by Visible-Light

A visible-light-induced metal-free desulfurization method for thiols and disulfides has been explored. This radical desulfurization features mild conditions, robustness, and excellent functionality compatibility. It was successfully applied not only to the desulfurization of small molecules, but also to peptides.

Catalytic study of the copper-based magnetic nanocatalyst on the aerobic oxidation of alcohols in water

A copper-based magnetic nanocatalyst has been prepared by co-precipitation method and characterized by FESEM, EDS, TEM, XRD, XRF, ICP–OES, FTIR, and BET analysis. This new nanocatalyst displays a good activity toward the aerobic oxidation of a wide range of alcohols in water. Moreover, it is recyclable up to five following runs by simple filtration without any significant loss of its catalytic activity.

SBA-15 Supported 1-Methyl-2-azaadamanane N-Oxyl (1-Me-AZADO) as Recyclable Catalyst for Oxidation of Alcohol

Herein, we designed and synthesized an SBA-15 supported 1-methyl-2-azaadamanane N-oxyl (1-Me-AZADO) and investigated its catalytic performance for selective oxidation of alcohols under Anelli's conditions. The first example of immobilization of 1-Me-AZADO was very important to advance the oxgenation effectively because this supported N-oxyl has excellent catalytic activity for oxidation of alcohols to carbonyl compounds, and more importantly, it can be conveniently recovered and reused at least 6 times without significant effect on its catalytic efficiency.

A TEMPO-Functionalized Ordered Mesoporous Polymer as a Highly Active and Reusable Organocatalyst

The properties of high stability, periodic porosity, and tunable nature of ordered mesoporous polymers make these materials ideal catalytic nanoreactors. However, their application in organocatalysis has been rarely explored. We report herein for the first time the incorporation of a versatile organocatalyst, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), into the pores of an FDU-type mesoporous polymer via a pore surface engineering strategy. The resulting FDU-15-TEMPO possesses a highly ordered mesoporous organic framework and enhanced stability, and shows excellent catalytic activity in the selective oxidation of alcohols and aerobic oxidative synthesis of 2-substituted benzoxazoles, benzimidazoles and benzothiazoles. Moreover, the catalyst can be easily recovered and reused for up to 7 consecutive cycles.

Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl

A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.

Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide

Chlorine is the 20th most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst, selective oxidation over chlorination of primary and secondary alcohols and their ethers with electron-donating substituents was achieved. The reagent precursor of NCBSI was recovered quantitatively and can be reused for synthesizing NCBSI.

Fine-Bubble-Slug-Flow Hydrogenation of Multiple Bonds and Phenols

We describe a promising method for the continuous hydrogenation of alkenes or alkynes by using a newly developed fine-bubble generator. The fine-bubble-containing slug-flow system was up to 1.4 times more efficient than a conventional slug-flow method. When applied in the hydrogenation of phenols to the corresponding cyclohexanones, the fine bubble-slug-flow method suppressed over-reduction. As this method does not require the use of excess gas, it is expected to be widely applicable in improving the efficiency of gas-mediated flow reactions.

A tunable synthesis of either benzaldehyde or benzoic acid through blue-violet LED irradiation using TBATB

In this paper, a highly efficient, metal-free, and homogeneous method for the selective aerobic photooxidation of alcohols and photooxidative-desilylation of tert-butyldimethylsilyl ethers (TBDMS) in the presence of tetrabutylammonium tribromide (TBATB) under irradiation of visible light was reported. The light source: blue (460 nm) and violet (400 nm) LED, can control selective oxidation to aldehyde or carboxylic acid.