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

Occurrence

Reported found in roasted filberts, green tea, cooked and roasted shrimp.

Uses

5-Methyl-3-hexen-2-one was used in combinatorial synthesis of mercaptoketones and mercaptoalcohols.

General Description

5-methyl-3-hexen-2-one reacts with indole in the presence of pyrrolidine and p-TsOH in CH2Cl2 to yield the 3-substituted indole adduct.

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

Upstream product

• 78-84-2 isobutyraldehyde 
• 67-64-1 acetone 
• 98428-27-4 5-isopropyl-3-methyl-4,5-dihydro-1H-pyrazole 
• 18815-73-1 methylzinc iodide 
• 65651-63-0 4-hydroxy-5-methyl-hexan-2-one 
• 7553-56-2 iodine 
• 28332-44-7 5-methylhex-4-en-2-one 
• 67-56-1 methanol 
• 541-50-4 2-acetoacetic acid 
• 590-86-3 isovaleraldehyde 
• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 56161-54-7 2-methyl-2-(2-(phenylsulfonyl)ethyl)-1,3-dioxolane 
• 75-26-3 isopropyl bromide 
• 869096-24-2 9-tolylsulfonyl-4,9-dihydro-3H-β-carboline 

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 
• 40238-92-4 4-ethyl-5-methyl-hexane-2-one 
• 120609-18-9 (+/-)-5-methyl-4-phenylhexan-2-one 
• 435269-66-2 (S)-5-methyl-4-phenylhexan-2-one 
• 162239-77-2 (R)-5-methyl-4-phenyl-hexan-2-one 

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.

Oxidative asymmetric formal aza-Diels–Alder reactions of tetrahydro-β-carboline with enones in the synthesis of indoloquinolizidine-2-ones

Ru-catalyzed tandem amine oxidative dehydrogenation/formal aza-Diels–Alder reaction for enantio- and diastereoselective synthesis of indoloquinolizidine-2-ones from tetrahydro-β-carbolines and α,β-unsaturated ketones is described. The reaction proceeds via tandem ruthenium-catalyzed amine dehydrogenation using tert-butyl hydroperoxide (TBHP) as the oxidant and a chiral thiourea-catalyzed formal aza-[4 + 2] cycloaddition, providing a step-economical strategy for the synthesis of these valuable heterocyclic products.

PYRIDINETHIONES, PHARMACEUTICAL COMPOSITIONS THEREOF, AND THEIR THERAPEUTIC USE FOR TREATING A PROLIFERATIVE, INFLAMMATORY, NEURODEGENERATIVE, OR IMMUNE-MEDIATED DISEASE

Provided herein are pyridinethiones, for example, a compound of Formula I, and pharmaceutical compositions thereof. Also provided herein are methods of their use for treating, preventing, or ameliorating one or more symptoms of a proliferative, inflammatory, neurodegenerative, or immune-mediated disease (e.g., multiple sclerosis).