3240-09-3

Basic information

• Product Name: 5-METHYL-5-HEXEN-2-ONE
• Synonyms: 5-methyl-5-hexen-2-on;FEMA 3365;5-METHYL-5-HEXEN-2-ONE;2-METHYL-1-HEXENE-5-ONE;5-methylhex-5-en-2-one;5-Hexen-2-one, 5-methyl-
• CAS NO: 3240-09-3
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.17
• EINECS: 221-807-6
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 3240-09-3.mol

Chemical Properties

• Boiling Point: 148-149 °C(lit.)
• Flash Point: 108 °F
• Appearance: /
• Density: 0.865 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.45mmHg at 25°C
• Refractive Index: n20/D 1.431(lit.)
• CAS DataBase Reference: 5-METHYL-5-HEXEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-5-HEXEN-2-ONE(3240-09-3)
• EPA Substance Registry System: 5-METHYL-5-HEXEN-2-ONE(3240-09-3)

Safety Data

• Hazard Codes: Xn
• Statements: 10-22-41
• Safety Statements: 26-39
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 3240-09-3(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
5-METHYL-5-HEXEN-2-ONE is used as a fragrance ingredient for its fresh, green, and leafy scent. It is commonly used in the formulation of perfumes, colognes, and other personal care products to provide a natural and refreshing aroma.
Used in Flavor Industry:
5-METHYL-5-HEXEN-2-ONE is used as a flavor ingredient for its green, fruity, and slightly woody taste. It is widely used in the food and beverage industry to add a natural and complex flavor to various products, such as soft drinks, candies, and chewing gum.
Used in Cosmetics Industry:
5-METHYL-5-HEXEN-2-ONE is used as an additive in the cosmetics industry to provide a pleasant and natural scent to various cosmetic products, such as lotions, creams, and shampoos.
Used in Agrochemical Industry:
5-METHYL-5-HEXEN-2-ONE is used as a semiochemical in the agrochemical industry. It serves as a pheromone for certain insects, such as the codling moth, and is used in pest control strategies to attract and trap these pests, reducing the need for chemical pesticides.
Used in Research and Development:
5-METHYL-5-HEXEN-2-ONE is used as a research compound in the development of new fragrances, flavors, and other applications. Its unique properties make it an important tool for scientists and researchers working in the fields of chemistry, biology, and materials science.

Preparation

From methallyl alcohol, the corresponding methallyl alcohol, acetoacetone is prepared, dissolved in diphenyl ether, and finally heated to between 200 and 215°C

InChI:InChI=1/C7H12O/c1-6(2)4-5-7(3)8/h1,4-5H2,2-3H3

Upstream product

• 5459-45-0 2-methylprop-2-enyl 3-oxobutanoate 
• 141-97-9 ethyl acetoacetate 
• 563-47-3 3-Chloro-2-methylpropene 
• 50551-88-7 5-methylhex-5-en-2-ol 
• 1458-98-6 2-methyl-3-bromo-1-propene 
• 123-54-6 acetylacetone 
• 7165-13-1 acetic butyric anhydride 
• 20962-70-3 ethyl 2-acetyl-4-methylpent-4-enoate 
• 113124-14-4 5-benzoyloxy-2-methyl-1-hexene 
• 59694-06-3 2,5-hexanediol monobenzoate 
• 100612-64-4 5-benzoyloxy-2-hexanone 
• 2935-44-6 hexane-2,5-diol 
• 79184-83-1 dimethylhydrazone of 2-methylhex-1-en-5-one 
• 162707-89-3 3-(Benzothiazol-2-ylsulfanyl)-5-methyl-hex-5-en-2-one 

Downstream Products

• 129976-61-0 3-hydroxy-6-methoxy-3,5-dimethyl-1,2-dioxane 
• 110-13-4 2,5-hexanedione 
• 133700-21-7 1,4-dimethylbicyclo<3.2.0>hept-3-en-6-one 
• 1449677-99-9 C₁₆H₂₀O 
• 1449677-95-5 C₁₅H₁₇ClO 
• 1449677-89-7 C₁₅H₁₈O 

Relevant articles and documents

Three-step synthetic pathway to fused bicyclic hydantoins involving a selenocyclization step

Sequential 5-alkenyl hydantoin and pyrrolidine ring-forming reactions have been applied in the synthesis of conformationally constrained fused bicyclic scaffold. They are assembled by a three-step reaction sequence from two variable building blocks (readily available β-ketoesters and alkenyl halides) by combining a Bucherer-Bergs reaction with a final selenium-promoted intramolecular cyclization as a key step. The chemoselectivity of this bicyclic hydantoin formation is strongly influenced by experimental factors such as the solvent and the use of additives. The reaction is regiospecific giving only five-membered fused bicyclic hydantoins in good to excellent yields stemming from the nucleophilic attack of the nitrogen atom to a cyclic seleniranium ion intermediate during the cyclization step. A separable diastereomeric mixture is obtained; the products with bridgehead substituents and phenylseleno groups in cis relationships were formed predominantly. The reaction tolerates a variety of substitution at the double bond, furthermore, the presence of substituents at C(5) and N(3) position opens up the capability of generating a broad structural diversity.

Halonium ion-mediated reaction of unsaturated hydroperoxy acetals. Competition between the formation of cyclic peroxides and the migration of the methoxy (or hydroxy) group

Monoozonolyses of dienes 2 in methanol gave in each case the corresponding unsaturated α-methoxy hydroperoxides 3. Capture of 2-alkyl- substituted cyclohexanone oxides by methanol was highly diastereoselective, thereby providing exclusively the hydroperoxides derived from attack by methanol from the less hindered face of the carbonyl oxide intermediates. Halonium ion-mediated reactions of the hydroperoxides 3 gave the novel methoxy- or hydroxy-migrated products, together with the expected halogen- substituted 1,2-dioxanes and/or 1,2-dioxepanes, the composition of the product mixture being a function of the halogenating agent utilized and the structure of 3.

Palladium-catalysed Synthesis of α-Diallylated Ketosulphides of Benzothiazole and their Transformation into Diallyl Thiiranes and Trienes

α-Ketosulphides of benzothiazole 1 react with allylic carbonates in the presence of palladium acetate in dichloromethane under mild conditions affording α,α-diallylated ketosulphides 2 in high yields.Reduction of 2 with sodium borohydride in isopropanol gives episulphides which in turn can be transformed almost quantitatively into trienes.

Oxymetallation. Part 24. Preparation of cyclic peroxides by cycloperoxymercuriation of unsaturated hydroperoxides

Seventeen unsaturated hydroperoxides have been converted by treatment with mercury(II) acetate and/or mercury(II) nitrate into nineteen new mercuriated cyclic peroxides and by subsequent demercuriation with alkaline sodium borohydride, six new mercury-free peroxides have been isolated. The results greatly extend the range of such reactions and provide information about the stereoselectivities and relative ease of several different modes of cycloperoxymercuriation. It is suggested that the reactions with mercury(II) acetate are kinetically controlled whereas those with mercury(II) nitrate show a component of thermodynamic control of product distribution.

Convenient Method for the Synthesis of Lineatin, a Pheromone Component of Trypodendron lineatum

Synthesis of racemic lineatin (1), a pheromone component of Trypodendron lineatum, is described.Condensation of 5-methyl-5-hexen-2-one (2) and triethyl phosphonoacetate with LiN(SiMe3)2 gave esters 3, which upon hydrolysis gave acids 4a-f.The bicyclo ring compounds 5 and 6 were obtained via an intramolecular addition by refluxing underivatized carboxylic acids 4a-f with NaOAc and Ac2O.Compound 5 was isomerized to the thermodynamically more stable isomer 6 using a Pd/C catalyst activated with hydrogen.Reduction of 6 with LiAlH4 gave the endo and exo isomers 7a and 7b (4:1).Isolation of the alcohol 7a followed by acetylation gave 8.Subsequent oxidation with OsO4 and methylmorpholine N-oxide gave diol 9.Cleavage of 9 with H5IO6 in diethyl ether gave keto aldehyde 10, which was converted to keto acetal 11.Treatment of 11 with MeMgBr followed by acidic workup gave 1.The overall efficiency is ca. 20percent.

Phosphorus-containing cyclic nitroxide free radicals

A nitroxide radical of the formula (I) or (II): STR1 in which R1 and R2 are independently chosen from among the optionally deuterated alkyl, alkoxyl, dialkylaminyl and phenyl radicals, H, D or Cl; R3, R8 and R9 are independently chosen from among the optionally deuterated alkyl, alkoxyl and phenyl radicals; R4, R5, R6 and R7 are independently chosen from among the optionally deuterated alkyl, alkoxyl, dialkylaminyl and phenyl radicals, COOH, OH, OD, H, D, a halogen, COOR (in which R is an alkyl radical); R10 and R11 are independently chosen from among optionally deuterated alkyl, alkoxyl, dialkylaminyl and phenyl radicals, COOH, OH, OD, H, D, a halogen, COOR (in which R is an alkyl radical) or represent an oxygen atom linked with the cycle of the radical by a double bond is described.

Ozonolsysis of 1,4-disubstituted 1,3-cyclohexadienes and of related compounds in methanol

Ozonolysis of 1,4-dimethyl- (5a) and 1-methyl-4-isopropyl-1,3-cyclohexadiene (5b) in methanol occur stepwise by sequential cleavage of the two double bonds.Monoozonolysis products are the corresponding compounds 6 and 7, and diozonolysis products are the corresponding cyclic peroxides 19, 20, and 21.By contrast, ozonolysis of the non-conjugated diene 2,5-dimethyl-1,5-hexadiene (13) in methanol occurs by simultaneous mono- and diozonolysis to give 14, 16a, 18a, and 20a.

Preparation of Unsaturated Hydroperoxides from N-Alkenyl-N'-p-tosylhydrazines

Unsaturated hydroperoxides (R1R2CHO2H), 2-phenylpent-4-enyl hydroperoxide (1), 3-phenylhex-5-en-2-yl hydroperoxide (2), 5-methylhex-5-en-2-yl hydroperoxide (3), cyclo-oct-4-enyl hydroperoxide (18), and cyclo-oct-3-enyl hydroperoxide (24) have each been prepared from the corresponding carbonyl compound (R1R2CO) by the sequence: i, conversion to the p-tosylhydrazone (R1R2C=N-NHTs); ii, reduction with sodium cyanoborohydride at pH 3.5 to give the N'-p-tosylhydrazine (R1R2CH-NH-NHTs); and iii, oxidation with hydrogen peroxide and sodium peroxide.Isomerisation occurs in the preparation of the cyclo-octenyl hydroperoxides, particuarly if the pH falls markedly below 3.5 in the reduction step.

Chemo-Selectivity of Group-VIII Metal Catalysts in Hydrogenation of Nonconjugated Enones

The chemo-selectivity of group-VIII metal catalysts has been examined in the hydrogenation of nonconjugated enones at ambient temperature under an atmospheric pressure of hydrogen.A cobalt catalyst gave high yields of unsaturated alcohols from trialkylated olefinic ketones.Osmium showed the highest selectivity among platinum metal catalysts for the reduction of the carbonyl bond in the hydrogenation of trialkylated olefinic ketones.The hydrogenation of mono- and dialkylated olefinic ketone ordinarily proceeded with a preferential saturation of the olefinic function, regardless of the catalysts.The hydrogenation of 4-methylene- and 4-ethylidenecyclohexanone was accompanied by the formation of diethyl acetals over ruthenium, rhodium, and palladium black catalysts in an ethanol solvent.The acetals were not detected in the hydrogenation of the other enones and over the other catalysts.In addition, the chemoselectivity on the hydrogenation of acyclic enones was examined over nickel and cobalt catalysts treated with small amounts of alkali and carbon monoxide.The amount of unsaturated alcohols increased when the catalyst was treated with alkali in the case of di- and trialkylated olefinic ketones, whereas the characteristics of cobalt, which selectively reduces the ketonic function in trialkylated olefinic ketoones, were completely missing when cobalt was treated with carbon monoxide.