13487-30-4

Basic information

• Product Name: 2,6,6-trimethylcyclohexa-2,4-dienone
• Synonyms: 2,6,6-trimethylcyclohexa-2,4-dienone;2,6,6-Trimethyl-2,4-cyclohexadien-1-one;Einecs 236-800-3;2,6,6-TriMethyl-2,4-cyclohexadienone
• CAS NO: 13487-30-4
• Molecular Formula: C₉H₁₂O
• Molecular Weight: 136.19098
• EINECS: 236-800-3
• Mol File: 13487-30-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 204.8 °C at 760 mmHg
• Flash Point: 77.9 °C
• Appearance: /
• Density: 0.933 g/cm³
• Vapor Pressure: 0.259mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: 2,6,6-trimethylcyclohexa-2,4-dienone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6,6-trimethylcyclohexa-2,4-dienone(13487-30-4)
• EPA Substance Registry System: 2,6,6-trimethylcyclohexa-2,4-dienone(13487-30-4)

Safety Data

• Hazardous Substances Data: 13487-30-4(Hazardous Substances Data)

Usage

General Description

2,6,6-trimethylcyclohexa-2,4-dienone is a chemical compound with the molecular formula C9H12O. It is a cyclic ketone that contains a cyclohexadienone ring structure. 2,6,6-trimethylcyclohexa-2,4-dienone is commonly used as a fragrance ingredient in perfumes and cosmetics due to its sweet and floral aroma. It is also used in the production of flavors and as a chemical intermediate in the synthesis of other compounds. Additionally, 2,6,6-trimethylcyclohexa-2,4-dienone has been studied for its potential application in organic synthesis and pharmaceutical research. Due to its chemical structure and properties, it has potential uses in a variety of industries and scientific fields.

InChI:InChI=1/C9H12O/c1-7-5-4-6-9(2,3)8(7)10/h4-6H,1-3H3

Upstream product

• 526-73-8 1,2,3-trimethylbenzene 
• 576-26-1 2.6-dimethylphenol 
• 74-88-4 methyl iodide 
• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 
• 59822-10-5 (+/-)-5-bromo-3-methyl-1-pentene 
• 85219-18-7 2,6,6-trimethyl-5-pyrrolidino-cyclohex-2-enone 
• 74768-99-3 2,6,6-Trimethyl-4-(phenylselenyl)-2-cyclohexen-1-on 
• 107536-93-6 (+/-)-4-acetoxy-2,6,6-trimethyl-2-cyclohexenone 
• 74768-98-2 4-bromo-2,6,6-trimethyl-2-cyclohexen-1-one 
• 19620-37-2 (+/-)-4-hydroxy-2,6,6-trimethyl-2-cyclohexenone 

Downstream Products

• 5986-55-0 (+/-) patchoulol 
• 17806-54-1 (4aR,6S,8aR)-4,8a,9,9-Tetramethyl-4a,5,6,7,8,8a-hexahydro-2H-1,6-methano-naphthalen-1-ol 
• 69903-52-2 1-[3-oxo-pent-4-en-1-yl]-1-trimethylsilyloxy-2,6,6-trimethylcyclohexa-2,4-diene 
• 75253-61-1 5-(1-Hydroxy-2,6,6-trimethylcyclohexa-2,4-dienyl)-1-penten-3-one 
• 75253-62-2 5-(2,3,6-trimethylphenyl)-1-penten-3-one 
• 59700-21-9 methyl-3 (trimethyl-2,3,6 phenyl)-5 pentene-1 ol-3 
• 79862-13-8 2,3,6-trimethyl-1-(3-methyl-4-penten-1-yl)benzene 
• 54702-01-1 (S)-2,6,6-Trimethyl-1-(3-methyl-pent-4-enyl)-cyclohexa-2,4-dienol 
• 100084-46-6 1,11,11-Trimethyl-4-phenyl-2,4,6-triazatricyclo<5.2.2.0^2,6>undec-8-en-3,5,10-trion 

Relevant articles and documents

A New Access to 2,6,6-Trimethylcyclohexa-2,4-dienone from 4-Oxoisophorone

2,6,6-Trimethylcyclohexa-2,4-dienone (1), a versatile starting material for the preparation of some carotenoids and several natural products, was efficiently (73 percent yield) prepared from oxoisophorone 3.After conversion of 3 to the alcohol 4 or the acetate 5, H2O was eliminated (4 -> 1) under acidic distillative conditions, whereas AcOH could be eliminated (5 -> 1) under Pd(O) catalysis.

Addition of Vinylketenes to Enamines. A Method for the Preparation of 6,6-Dialkylcyclohexa-2,4-dienones and 4,4-Dialkyl-2-vinylcyclobutenones

Drei Enamine (1-3) wurden mit fuenf Vinylketenen (5a-5e) (s.Schema 2) zur Reaktion gebracht.Die Vinylketene wurde in situ durch HCl-Eliminierung aus α,β-ungesaettigten Saeurechloriden mit Triaethylamin hergestellt.Die Cycloadditionen von 1-3 an 5a-5e fuehrten zu 6,6-Dialkyl-5-dialkylaminocycohex-2-enonen (kurz: Cyclohexenone) bzw. zu 3-Dialkylamino-4,4-dimethyl-2-vinylcyclobutanonen (kurz: Vinylcyclobutanone) oder zu einem Gemisch der beiden, je nach Natur der Partner bzw. des Loesungsmittels (s.Tab. 1).Durch oxidative Amin-Eliminierung wurden die Cyclohexenone in 6,6-Dialkylcyclohexa-2,4-dienone und die Vinylcyclobutanone in 4,4-Dialkyl-2-vinylcyclobutenone uebergefuehrt.Diese Reaktion stellt eine einfache Synthese von verschieden substituierten 6,6-Dialkylcyclohexa-2,4-dienonen bzw. 4,4-Dialkyl-2-vinylcyclobutenonen (siehe Schema 1) dar.

Light-induced Reactions, XIV. Rules for Determining Spectra of 2,4-Cyclohexadien-1-ones

2,4-Cyclohexadien-1-ones of formula types 1 to 5 (cf.Fig. 1) provide basic values and positional increments for UV and 13C NMR spectra.These parameters allow to distinguish between constitutional isomers belonging to one and the same column of the graph of Fig. 1.It has become possible, e.g., to identify clearly the constitutional isomers 6 and 8 or 12 and 14, respectively.