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

Uses

2,2-Dimethylcyclohexanone may be used in the preparation of 6,6-dimethyl-1-vinylcyclohexene.

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

General Description

2,2-Dimethylcyclohexanone is a sterically hindered ketone. Mg-TiCl4-catalyzed CH2-transfer reaction of 2,2-dimethylcyclohexanone with CH2Cl2 is reported.

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

Upstream product

• 5212-66-8 2-(Bromomethyl)-2-methylcyclohexanone 
• 583-60-8 2-Methylcyclohexanone 
• 854435-09-9 (+/-)-1.1-dimethyl-3-benzoyl-cyclohexanone-⁽²⁾ 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 1193-46-0 2,2-dimethylcyclohexanol 
• 7443-52-9 (+/-)-trans-2-methylcyclohexanol 
• 7443-70-1 cis-2-methylcyclohexanol 
• 286-20-4 cyclohexene oxide 
• 56475-48-0 6-iodo-2,2-dimethylhexanenitrile 
• 1056595-84-6 C₈H₁₅NO 
• 590-66-9 1,1-dimethylcyclohexane 
• 19700-21-1 (-)-geosmin 
• 7722-84-1 dihydrogen peroxide 
• 15409-53-7 6-methyl-2-(hydroxymethylene)cyclohexanone 

Downstream Products

• 64692-82-6 2,2-dimethylcyclohexanone (p-tolylsulfonyl)hydrazone 
• 73839-49-3 2,2-dimethylcyclohexanone benzenesulfonylhydrazone 
• 89328-75-6 (+/-)-2,2-dimethyl-6-propenylcyclohexanone 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 936331-85-0 C₁₂H₁₇NO₃ 
• 1193-46-0 2,2-dimethylcyclohexanol 
• 7479-48-3 2,2-dimethylcyclohexanone semicarbazone 
• 32363-23-8 6,6-dimethylcyclohex-1-en-1-yl trifluoromethanesulfonate 
• 4500-17-8 (E)-2,2-dimethylcyclohexanone oxime 
• 67218-06-8 6-(butylsulfanyl-methylene)-2,2-dimethyl-cyclohexanone 
• 91365-83-2 2,2-dimethyl-1-ethynyl-1-cyclohexanol 
• 122777-56-4 ethyl 2-(1-hydroxy-2,2-dimethylcyclohexyl)propionate 
• 113994-57-3 1-(p-methoxyphenylethynyl)-2,2-dimethylcyclohexanol 
• 101327-97-3 Methyl 3,3-dimethyl-2-oxocyclohexanecarboxylate 

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.

Catalyst-controlled aliphatic C—H oxidations

The invention provides simple small molecule, non-heme iron catalyst systems with broad substrate scope that can predictably enhance or overturn a substrate's inherent reactivity preference for sp3-hybridized C—H bond oxidation. The invention also provides methods for selective aliphatic C—H bond oxidation. Furthermore, a structure-based catalyst reactivity model is disclosed that quantitatively correlates the innate physical properties of the substrate to the site-selectivities observed as a function of the catalyst. The catalyst systems can be used in combination with oxidants such as hydrogen peroxide to effect highly selective oxidations of unactivated sp3 C—H bonds over a broad range of substrates.