1193-47-1

Basic information

• Product Name: 2,2-DIMETHYLCYCLOHEXANONE
• Synonyms: 2,2-Dimethyl-1-cyclohexanone;6,6-Dimethylcyclohexanone;2,2-DIMETHYLCYCLOHEXANONE;2,2-dimethylcyclohexan-1-one;2,2-Dimethylcyclohexanone ,93%;2,2-Dimethylcyclohexanone 92%
• CAS NO: 1193-47-1
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.2
• EINECS: 215-589-1
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 1193-47-1.mol
• Article Data: 57

Chemical Properties

• Melting Point: −20 °C(lit.)
• Boiling Point: 169-170 °C768 mm Hg(lit.)
• Flash Point: 122 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.912 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.46mmHg at 25°C
• Refractive Index: n20/D 1.448(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,2-DIMETHYLCYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYLCYCLOHEXANONE(1193-47-1)
• EPA Substance Registry System: 2,2-DIMETHYLCYCLOHEXANONE(1193-47-1)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 1193-47-1(Hazardous Substances Data)

Usage

Description

2,2-Dimethylcyclohexanone is a sterically hindered ketone, which means it has bulky groups on the molecule that can limit its reactivity. It is known for its unique chemical properties and potential applications in various industries.

Uses

Used in Chemical Synthesis:
2,2-Dimethylcyclohexanone is used as an intermediate in the chemical synthesis of various compounds. Its steric hindrance makes it a valuable component in the preparation of specific molecules.
Used in the Preparation of 6,6-Dimethyl-1-Vinylcyclohexene:
2,2-Dimethylcyclohexanone is used as a starting material for the preparation of 6,6-dimethyl-1-vinylcyclohexene, which is an important compound in the synthesis of various chemicals and materials.
Used in the Chemical Industry:
In the chemical industry, 2,2-dimethylcyclohexanone is used as a reactant in various reactions, taking advantage of its unique steric properties to control the outcome of the reactions and produce desired products.
Used in Research and Development:
Due to its unique chemical structure, 2,2-dimethylcyclohexanone is also used in research and development for studying the effects of steric hindrance on chemical reactions and exploring new synthetic pathways.
General Description and Production Methods:
2,2-Dimethylcyclohexanone can be synthesized through various methods, one of which involves a Mg-TiCl4-catalyzed CH2-transfer reaction with CH2Cl2. This reaction highlights the versatility of 2,2-dimethylcyclohexanone in chemical transformations.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 1615, 1962 DOI: 10.1021/jo01052a031Tetrahedron, 33, p. 2737, 1977 DOI: 10.1016/0040-4020(77)80265-2Tetrahedron Letters, 24, p. 1341, 1983 DOI: 10.1016/S0040-4039(00)81651-2

InChI:InChI=1/C8H14O/c1-8(2)6-4-3-5-7(8)9/h3-6H2,1-2H3

Upstream product

• 5607-45-4 1-(2-hydroxyprop-2-yl)cyclopentanol 
• 74-83-9 methyl bromide 
• 108-94-1 cyclohexanone 
• 5212-66-8 2-(Bromomethyl)-2-methylcyclohexanone 
• 74-88-4 methyl iodide 
• 74752-30-0 3,3-dimethyl-cyclohexene Epoxide 
• 583-60-8 2-Methylcyclohexanone 
• 19980-35-9 1-trimethylsilyloxy-2-methyl-1-cyclohexene 
• 333-27-7 methyl trifluoromethanesulfonate 
• 7479-48-3 2,2-dimethylcyclohexanone semicarbazone 
• 60-29-7 diethyl ether 
• 1056595-84-6 C₈H₁₅NO 
• 56475-48-0 6-iodo-2,2-dimethylhexanenitrile 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 31720-69-1 1,2,2-trimethylcyclohexanol 
• 102943-34-0 1-hydroxy-2,2-dimethyl-cyclohexanecarbonitrile 
• 91365-83-2 2,2-dimethyl-1-ethynyl-1-cyclohexanol 
• 1193-46-0 2,2-dimethylcyclohexanol 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 33689-45-1 1-chloro-6,6-dimethyl-cyclohexene 
• 7479-48-3 2,2-dimethyl-cyclohexanone semicarbazone 
• 90089-61-5 6,6-dimethyl-2-chlorocyclohexanone 
• 4500-17-8 2,2-dimethylcyclohexanone oxime 
• 17622-50-3 6-benzylidene-2,2-dimethyl-cyclohexanone 
• 24247-77-6 2,2-dimethylcyclohexan-1-amine 
• 55233-98-2 ethyl 2-oxo-3,3-dimethyl-cyclohexanecarboxylate 
• 5212-74-8 2,2-dimethyl-cyclohexanone-(2,4-dinitro-phenylhydrazone) 
• 1195-93-3 2,2,6,6-tetramethylcyclohexanone 

Relevant articles and documents

First total synthesis and assignment of the stereochemistry of crispatenine

(Figure Presented) The first racemic and enantioselective synthesis of crispatenine 1 has been achieved, which involved a few steps, enabling the assignment of the absolute and relative configurations.

Sequential hydroformylation/aldol addition reactions of β,γ- unsaturated ketones and their derivatives

Novel rhodium(I) complex catalysed tandem hydroformylation/aldol reactions of a β,γ-unsaturated ketone 1 or its silyl enol ethers 4 in a one-pot procedure are presented to give varying cyclisation products depending on the reaction conditions.

-

-

Stereoselective Synthesis of 1-Tuberculosinyl Adenosine; A Virulence Factor of Mycobacterium tuberculosis

Despite its status as one of the world's most prevalent and deadly bacterial pathogens, Mycobacterium tuberculosis (Mtb) infection is not routinely diagnosed by rapid and highly reliable tests. A program to discover Mtb-specific biomarkers recently identified two natural compounds, 1-tuberculosinyl adenosine (1-TbAd) and N6-tuberculosinyl adenosine (N6-TbAd). Based on their association with virulence, the lack of similar compounds in nature, the presence of multiple stereocenters, and the need for abundant products to develop diagnostic tests, synthesis of these compounds was considered to be of high value but challenging. Here, a multigram-scale stereoselective synthesis of 1-TbAd and N6-TbAd is described. As a key-step, a chiral auxiliary-mediated Diels-Alder cycloaddition was developed, introducing the three stereocenters with a high exo endo ratio (10:1) and excellent enantioselectivity (>98% ee). This constitutes the first entry into the stereoselective synthesis of diterpenes with the halimane skeleton. Computational studies explain the observed stereochemical outcome.

5-MEMBERED HETEROARYLAMINOSULFONAMIDES FOR TREATING CONDITIONS MEDIATED BY DEFICIENT CFTR ACTIVITY

The invention relates to heteroaryl compounds, pharmaceutically acceptable salts thereof, and pharmaceutical preparations thereof. Also described herein are compositions and the use of such compounds in methods of treating diseases and conditions mediated by deficient CFTR activity, in particular cystic fibrosis.

(Poly)cationic λ3-Iodane-Mediated Oxidative Ring Expansion of Secondary Alcohols

Herein, a simplified approach to the synthesis of medium-ring ethers through the electrophilic activation of secondary alcohols with (poly)cationic λ3-iodanes (N-HVIs) is reported. Excellent levels of selectivity are achieved for C–O bond migration over established α-elimination pathways, enabled by the unique reactivity of a novel 2-OMe-pyridine-ligated N-HVI. The resulting hexafluoroisopropanol (HFIP) acetals are readily derivatized with a range of nucleophiles, providing a versatile functional handle for subsequent manipulations. The utility of this methodology for late-stage natural product derivatization was also demonstrated, providing a new tool for diversity-oriented synthesis and complexity-to-diversity (CTD) efforts. Preliminary mechanistic investigations reveal a strong effect of alcohol conformation on the reactive pathway, thus providing a predictive power in the application of this approach to complex molecule synthesis.