5166-53-0

Basic information

• Product Name: 5-METHYL-3-HEXEN-2-ONE
• Synonyms: 5-METHYL-3-HEXEN-2-ONE;5-METHYLHEX-3-EN-2-ONE;FEMA 3409;5-METHYL-3-HEXEN-2-ONE, TECH., 80%;3-Hexen-2-one, 5-methyl-;3-HEXAN-2-ONE,5-METHYL;5-Methyl-3-hexene-2-one;5-Methyl-2-oxohex-3-ene
• CAS NO: 5166-53-0
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.17
• EINECS: 225-950-5
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 5166-53-0.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 157°C
• Flash Point: 118 °F
• Appearance: /
• Density: 0.85 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.8mmHg at 25°C
• Refractive Index: n20/D 1.44(lit.)
• CAS DataBase Reference: 5-METHYL-3-HEXEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-3-HEXEN-2-ONE(5166-53-0)
• EPA Substance Registry System: 5-METHYL-3-HEXEN-2-ONE(5166-53-0)

Safety Data

• Hazard Codes: Xn,T
• Statements: 10-20/21/22-24-20/22
• Safety Statements: 16-27-36/37/39-45-36/37
• RIDADR: UN 1992 3/PG 3
• WGK Germany: 3
• RTECS: MP8750000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 5166-53-0(Hazardous Substances Data)

Usage

Description

5-METHYL-3-HEXEN-2-ONE is an organic compound that is known for its distinctive green, leafy, and slightly fruity odor. It is a naturally occurring compound found in various food items and is often used in the synthesis of other compounds.

Uses

Used in Flavor and Fragrance Industry:
5-METHYL-3-HEXEN-2-ONE is used as a flavoring agent for its characteristic green, leafy, and slightly fruity aroma. It is commonly added to food products to enhance their natural flavors, particularly in products that aim to replicate the taste of green vegetables or fruits.
Used in Chemical Synthesis:
5-METHYL-3-HEXEN-2-ONE is used as a key intermediate in the combinatorial synthesis of mercaptoketones and mercaptoalcohols. These synthesized compounds have various applications in the chemical industry, including the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 5-METHYL-3-HEXEN-2-ONE is often utilized in research and development for the creation of new compounds and materials. Its ability to react with indole in the presence of pyrrolidine and p-TsOH in CH2Cl2 to yield the 3-substituted indole adduct makes it a valuable compound for exploring new chemical reactions and applications.
Occurrence:
5-METHYL-3-HEXEN-2-ONE is naturally found in a variety of food items, including roasted filberts, green tea, and cooked and roasted shrimp. Its presence in these products contributes to their distinct flavors and aromas, making it an important compound in the food industry.

InChI:InChI=1/C7H12O/c1-6(2)4-5-7(3)8/h4-6H,1-3H3

Upstream product

• 65651-63-0 4-hydroxy-5-methyl-hexan-2-one 
• 78-84-2 isobutyraldehyde 
• 67-64-1 acetone 
• 56161-54-7 2-methyl-2-(2-(phenylsulfonyl)ethyl)-1,3-dioxolane 
• 75-26-3 isopropyl bromide 
• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 98428-27-4 5-isopropyl-3-methyl-4,5-dihydro-1H-pyrazole 
• 18815-73-1 methylzinc iodide 
• 7553-56-2 iodine 
• 590-86-3 isovaleraldehyde 
• 60-29-7 diethyl ether 
• 4376-49-2 1-isopropyl-2,3-butadien-1-ol 
• 59697-04-0 5-methyl-4-(toluene-4-sulfonyloxy)-hexan-2-one 
• 28332-44-7 5-methylhex-4-en-2-one 

Downstream Products

• 28332-44-7 5-methylhex-4-en-2-one 
• 10321-71-8 4-methyl-pent-2-enoic acid 
• 759-05-7 3-methyl-2-ketobutanoic acid 
• 110-12-3 5-Methyl-2-hexanone 
• 1775-44-6 (2E)-4-methylpent-2-enoic acid 
• 18456-87-6 5-isopropyl-1,3-cyclohexanedione 
• 29210-63-7 4,5-diisopropyl-octane-2,7-dione 
• 92319-64-7 opt.-inakt. 2-Acetyl-3,4-dipropyl-1-methyl-cyclopentan-1-ol 
• 79083-88-8 4-(4-Chloro-phenyl)-5-methyl-hexan-2-one 
• 79083-91-3 1,4-Bis-(4-chloro-phenyl)-3-isopropyl-5-methyl-1H-pyrazole 
• 126571-48-0 1-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)-ethanone 
• 126571-50-4 1-(2-Isopropyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridin-3-yl)-ethanone 
• 75508-46-2 2-methyl-2-(3-methyl-but-3-enyl)-[1,3]dioxolane 
• 6611-92-3 5-methyl-4-hexen-2-one ethylene ketal 

Relevant articles and documents

Sc(OTf)3a'Catalyzed Ca'C Bond-Forming Reaction of Cyclic Peroxy Ketals for the Synthesis of Highly Functionalized 1,2-Dioxene Endoperoxides

A new and general Sc(OTf)3-catalyzed C-C bond-forming reaction of 3-(2-methoxyethoxy)-endoperoxy ketals with silyl ketene acetals, silyl enol ethers, allyltrimethylsilane, and trimethylsilyl cyanide has been developed via the reactive peroxycarbenium ions, affording a wide range of complicated 3,3,6,6-tetrasubstituted 1,2-dioxenes bearing adjacent quaternary carbons and 3-acetyl/allyl/cyano functional groups in good yields at room temperature. Notably, the resultant 1,2-dioxenes are structurally stable, which can be facially transformed into another important 1,2-dioxane endoperoxide under conventional hydrogenation conditions without deconstructing the weak O-O bond.

Discovery and optimization of novel benzothiophene-3-carboxamides as highly potent inhibitors of Aurora kinases A and B

Aurora kinases as regulators of cell division have become promising therapeutic targets recently. Here we report novel, low molecular weight benzothiophene-3-carboxamide derivatives designed and optimized for inhibiting Aurora kinases. The most effective compound 36 inhibits Aurora kinases in vitro in the nanomolar range and diminishes HCT 116 cell viability blocking cytokinesis and inducing apoptosis. According to western blot analysis, the lead molecule inhibits Aurora kinases equipotently to VX-680 (Tozasertib) and similarly synergizes with other targeted drugs.

Catalytic Asymmetric Conjugate Addition of Indolizines to α,β-Unsaturated Ketones

A catalytic enantioselective conjugate addition of indolizines to enones is described. The chiral phosphoric acid (S)-TRIP activates α,β-unsaturated ketones, thereby promoting an enantioface-differentiating attack by indolizines. Using this reaction, several alkylated indolizines were synthesized in good yields and with enantiomeric ratios of up to 98:2.