619-52-3

Basic information

• Product Name: 1-Isopropyl-4α-methylcyclohexene
• Synonyms: (1R)-p-Mentha-3-ene;[R,(+)]-p-Menth-3-ene;[R,(+)]-p-Mentha-3-ene;1-Isopropyl-4α-methylcyclohexene
• CAS NO: 619-52-3
• Molecular Formula: C₁₀H₁₈
• Molecular Weight: 138.25
• Mol File: 619-52-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 168.05°C
• Appearance: /
• Density: 0.8078
• Refractive Index: 1.4503
• CAS DataBase Reference: 1-Isopropyl-4α-methylcyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Isopropyl-4α-methylcyclohexene(619-52-3)
• EPA Substance Registry System: 1-Isopropyl-4α-methylcyclohexene(619-52-3)

Safety Data

• Hazardous Substances Data: 619-52-3(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Odor

Sweet, fruity

Primary use

Flavoring agent in food and beverage industry

Secondary use

Fragrance ingredient in cosmetics and personal care products

Potential application

Solvent in various industrial processes

Health and environmental impact

Not listed as having significant harmful effects, but should be handled with safety precautions.

Upstream product

• 79-37-8 oxalyl dichloride 
• 89-78-1 menthol 
• 115936-72-6 succinic acid dimenthyl ester 
• 37487-24-4 1,2,μ-trithio-dicarbonic acid O,O'-dimenthyl ester 
• 37487-20-0 bis disulfide 
• 2216-51-5 (-)-menthol 
• 144-62-7 oxalic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 172276-48-1 borneol p-toluenesulfonate 
• 141-52-6 sodium ethanolate 
• 91-66-7 N,N-diethylaniline 
• 77-92-9 citric acid 
• 10458-14-7 Menthone 
• 5564-44-3 O-(-)-menthyl S-methyl carbonodithioate 

Downstream Products

• 6070-07-1 (1R,3S,4R)-p-menthane-3,4-diol 
• 1079-58-9 acetic acid p-menth-4-en-3-yl ester 
• 187737-37-7 propene 
• 34557-54-5 methane 
• 74-84-0 ethane 
• 74-85-1 ethene 
• 99-87-6 4-methylisopropylbenzene 
• 470-65-5 p-menthane-4-ol 
• 4053-64-9 p-menthane-3,4-diol 
• 74219-28-6 2-hydroxy-2-isopropyl-5-methylcyclohexanone 
• 578-44-9 (+/-)-trans-p-menth-4-en-3-ol 
• 802828-84-8 p-menthan-4-ylamine 
• 7616-79-7 (1R,4S)-(+)-4-hydroxy-p-menth-3-one 
• 7599-95-3 4β-hydroxy-l-menthol 

Relevant articles and documents

(-)-Menthol as a source of new N,N-diamine ligands for asymmetric transfer hydrogenation

The synthesis of new chiral N-monotosylated-1,2-diamines based on the (-)-menthol skeleton is presented. The elimination of HCl from neomenthyl chloride obtained from an Appel reaction led to p-menth-3-ene in excellent yield. Further functionalization of the double bond in p-menth-3-ene with chloramine-T gave the corresponding N-tosylaziridines, which upon reaction with sodium azide and subsequent reduction of the azide functional group, formed the 1,2-diamine system. The synthesized chiral ligands proved effective in the asymmetric transfer hydrogenation of aromatic ketones and an endocyclic imine.

Clarification of the stereochemical course of nucleophilic substitution of arylsulfonate-based nucleophile assisting leaving groups

(Chemical Equation Presented) Secondary alcohols modified as tosylates, PEG-sulfonates, or quisylates undergo inversion of configuration at the reacting center when treated with lithium halide in acetone at reflux, where the PEG-sulfonates and quisylates are substantially more reactive. In sterically hindered cases, elimination is a competing process. In contrast, when treated with TiCl4, simple secondary sulfonates give chloride products with partial inversion of configuration. Any observed retention of configuration in a given alkyl sulfonate substrate under these conditions is likely due to neighboring group participation or diastereoselective attack on a carbocation (or ion pair) rather than an SNi mechanism.

Synthesis of the promising chiral synthon isopropyl-4R-methyl-6- iodohexanoate from L-(-)-menthol

A synthesis of the promising optically pure synthon isopropyl-4R-methyl-6- iodohexanoate based on ozonolytic transformation of the product of regiospecific dehydratation of L-(-)-menthol, (R)-p-menth-3-ene, into 2,6R-dimethyl-8- hydroxyoctan-3-one was proposed. 2005 Springer Science+Business Media, Inc.