13395-71-6

Basic information

• Product Name: 2,4,4-TRIMETHYL-2-CYCLOHEXEN-1-ONE
• Synonyms: 2,4,4-TRIMETHYL-2-CYCLOHEXEN-1-ONE;2 4 4-TRIMETHYL-2-CYCLOHEXEN-1-ONE 98%;2,4,4-TRIMETHYLCYCLOHEX-2-ENONE
• CAS NO: 13395-71-6
• Molecular Formula: C₉H₁₄O
• Molecular Weight: 138.21
• Mol File: 13395-71-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 158 °C
• Boiling Point: 81-82 °C20 mm Hg(lit.)
• Flash Point: 151 °F
• Appearance: /
• Density: 0.924 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.476(lit.)
• CAS DataBase Reference: 2,4,4-TRIMETHYL-2-CYCLOHEXEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,4-TRIMETHYL-2-CYCLOHEXEN-1-ONE(13395-71-6)
• EPA Substance Registry System: 2,4,4-TRIMETHYL-2-CYCLOHEXEN-1-ONE(13395-71-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13395-71-6(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Aroma

Strong, floral

Usage

Flavoring agent in food products, fragrance ingredient in perfumes and personal care products, synthesis of other chemicals

Safety

Generally considered safe for use in consumer products when used in specified concentrations, but should be handled and used according to recommended safety guidelines to minimize potential risks.

Upstream product

• 108-75-8 2,4,6-trimethyl-pyridine 
• 102872-72-0 2-bromo-2,4,4-trimethyl-cyclohexanone 
• 134736-78-0 (+/-)-2,4,4-Trimethyl-2-cyclohexen-1-ol 
• 1629-58-9 4-penten-3-one 
• 78-84-2 isobutyraldehyde 
• 20633-35-6 4-[1,3]dioxolan-2-yl-4-methyl-pentanenitrile 
• 925-90-6 ethylmagnesium bromide 
• 2403-57-8 1-(2-methylprop-1-en-1-yl)pyrrolidine 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 134736-79-1 (+/-)-2,4,4-Trimethyl-2-cyclohexenyl acetate 
• 60-29-7 diethyl ether 
• 564-24-9 (+/-)-α-cyclogeranic acid 
• 7553-56-2 iodine 
• 1600-27-7 mercury(II) diacetate 

Downstream Products

• 134780-16-8 (R)-2,4,4-trimethyl-2-cyclohexen-1-ol 
• 134780-17-9 (S)-2,4,4-trimethyl-2-cyclohexen-1-ol 
• 41169-33-9 3,5,5-trimethylcyclohexa-1,3-diene 
• 596100-76-4 (R)-1,2,4,4-Tetramethyl-cyclohex-2-enol 
• 684214-94-6 6-bromo-2,4,4-trimethyl-cyclohex-2-enone 
• 52646-93-2 [(S)-2,6,6-trimethylcyclohex-2-enyl]methanol 
• 14505-74-9 (S)-2,6,6-trimethylcyclohex-2-enecarbaldehyde 
• 116497-11-1 (2E)-1-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-2-en-1-one 
• 147753-66-0 (R)-2,4,4-trimethyl-2-cyclohexenyl 2-butynyl ether 
• 28102-24-1 (S)-α-damascol 
• 17522-32-6 (S)-dehydro-α-damascol 
• 472-64-0 (2,6,6-Trimethyl-2-cyclohexenyl)acetaldehyde 
• 1207109-99-6 6-hydroxymethylene-2,2,4,4-tetramethylcyclohexanone 
• 1207110-52-8 3,3,5,5-tetramethyl-2-oxocyclohexanecarbonitrile 

Relevant articles and documents

Protecting-Group-Free Syntheses of ent-Kaurane Diterpenoids: [3+2+1] Cycloaddition/Cycloalkenylation Approach

The Yu's Rh-catalyzed [3+2+1] cycloaddition followed by a Pd-mediated 5-endo cycloalkenylation is shown to be a general and powerful approach for efficient construction of the tetracyclic core structure of ent-kaurane diterpenoids. The utility of this strategy was further demonstrated by concise and protecting-group-free total syntheses of ent-1α-hydroxykauran-12-one, 12-oxo-9,11-dehydrokaurene, and 12α-hydroxy-9,11-dehydrokaurene.

Highly Active Cooperative Lewis Acid—Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones

Enantiopure secondary alcohols are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5–3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxophilic Lewis acid within the same catalyst molecule. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an SN2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working.

METHODS FOR PRODUCING BETA-CYCLOLAVANDULAL AND DERIVATIVE OF SAME

Target compounds are synthesized simply, efficiently and selectively. More specifically, provided are a method for producing (2,4,4-trimethyl-1-cyclohexene)carbaldehyde, comprising the steps of: reacting the carbonyl group of 2,4,4-trimethyl-2-cyclohexeno