564-24-9

Basic information

• Product Name: 2,6,6-trimethylcyclohex-2-ene-1-carboxylic acid
• Synonyms: 2,6,6-trimethylcyclohex-2-ene-1-carboxylic acid;2,6,6-Trimethyl-2-cyclohexene-1-carboxylic acid;2-Cyclohexene-1-carboxylic acid, 2,6,6-triMethyl-
• CAS NO: 564-24-9
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• EINECS: 209-270-6
• Mol File: 564-24-9.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 257.1°C at 760 mmHg
• Flash Point: 123.4°C
• Appearance: /
• Density: 0.999g/cm³
• Vapor Pressure: 0.00452mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: 2,6,6-trimethylcyclohex-2-ene-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6,6-trimethylcyclohex-2-ene-1-carboxylic acid(564-24-9)
• EPA Substance Registry System: 2,6,6-trimethylcyclohex-2-ene-1-carboxylic acid(564-24-9)

Safety Data

• Hazardous Substances Data: 564-24-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 9, p. 2851, 1968 DOI: 10.1016/S0040-4039(00)75645-0

InChI:InChI=1/C10H16O2/c1-7-5-4-6-10(2,3)8(7)9(11)12/h5,8H,4,6H2,1-3H3,(H,11,12)

Upstream product

• 459-80-3 geranic acid 
• 87877-75-6 (±)-3-hydroxy-3,7-dimethyloct-6-enoic acid 
• 861315-80-2 2,3-dibromo-2,6,6-trimethyl-cycloheptanone 
• 96849-99-9 ethyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate 
• 14505-74-9 α-cyclocitral 
• 61899-98-7 2,6,6-trimethylcyclohex-2-en-1-ylidene ketene 
• 65482-49-7 3-trimethylsilylmethyl-7-methyl-2,6-octadienoic acid 
• 4698-08-2 (E)-geranic acid 
• 64-18-6 formic acid 
• 73945-80-9 3,7-dimethyl-octa-2,7-dienoic acid 
• 7664-93-9 sulfuric acid 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 35836-89-6 2,6,6-trimethyl-2-cycloheptenone 
• 110-93-0 6-Methyl-hept-5-en-2-on 

Downstream Products

• 96849-99-9 ethyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate 
• 24190-30-5 (S)-α-cyclogeraniumsaeure 
• 52646-90-9 (R)-α-Cyclogeraniumsaeure 
• 4351-02-4 (+/-)-2,2,6c-trimethyl-cyclohexane-r-carboxylic acid 
• 6627-74-3 (+/-)-α-cyclogeraniol 
• 13395-71-6 2,4,4-trimethyl-2-cyclohexenone 
• 134736-78-0 (+/-)-2,4,4-Trimethyl-2-cyclohexen-1-ol 
• 52567-46-1 (+/-)-2.2.6t-trimethyl-cyclohexane-carboxylic acid-(1r)-chloride 
• 22471-55-2 (+/-)-2.2.6t-trimethyl-cyclohexane-carboxylic acid-(1r)-ethyl ester 
• 4351-02-4 (+/-)-2,2,6t-trimethyl-cyclohexane-r-carboxylic acid 
• 52567-47-2 (+/-)-2.2.6t-trimethyl-cyclohexane-carboxylic acid-(1r)-methyl ester 
• 23696-85-7 1-(2,6,6-trimethyl-1,3-cyclohexadiene-1-yl)-2-butene-1-one 
• 472-64-0 (2,6,6-Trimethyl-2-cyclohexenyl)acetaldehyde 
• 93737-24-7 1,1,3-Trimethyl-2-benzoylmethyl-cyclohexen-3 

Relevant articles and documents

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Methyl 3-oxo-2,6,6-trimethylcyclohex-1-ene-1-carboxylate was synthesised over eight steps from the starting material of citral instead of α-ionone. KMnO4, HC(OEt)3 and O2/TEMPO/CuCl were substituted for NaIO4, CH3I and pyridinium chlorochromate, respectively. Every step was simplified and gave a 48% overall yield. The procedure is suitable for large scale production.