2065-76-1

Basic information

• Product Name: 2,6-dibromo-3,3,5,5-tetramethylcyclohexan-1-one
• Synonyms: 2,6-dibromo-3,3,5,5-tetramethylcyclohexan-1-one;2,6-Dibromo-3,3,5,5-tetramethylcyclohexanone;Einecs 218-182-7
• CAS NO: 2065-76-1
• Molecular Formula: C₁₀H₁₆Br₂O
• Molecular Weight: 312.04144
• EINECS: 218-182-7
• Mol File: 2065-76-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 285.6°Cat760mmHg
• Flash Point: 62.6°C
• Appearance: /
• Density: 1.496g/cm³
• Vapor Pressure: 0.00278mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: 2,6-dibromo-3,3,5,5-tetramethylcyclohexan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dibromo-3,3,5,5-tetramethylcyclohexan-1-one(2065-76-1)
• EPA Substance Registry System: 2,6-dibromo-3,3,5,5-tetramethylcyclohexan-1-one(2065-76-1)

Safety Data

• Hazardous Substances Data: 2065-76-1(Hazardous Substances Data)

Usage

Structure

Highly substituted cyclohexanone derivative
The compound is derived from cyclohexanone, with various substituents attached to the ring.

Bromine atoms

Attached to the 2 and 6 positions
Two bromine atoms are present in the compound, located at the 2nd and 6th positions of the cyclohexane ring.

Methyl groups

Attached to the 3 and 5 positions
Four methyl groups are present in the compound, located at the 3rd and 5th positions of the cyclohexane ring.

Usage

Reagent in organic synthesis
The compound is commonly used in organic synthesis, particularly for the preparation of various substituted cyclohexanones and related compounds.

Application

Intermediate in pharmaceutical and agrochemical production
2,6-dibromo-3,3,5,5-tetramethylcyclohexan-1-one serves as an intermediate in the production of pharmaceuticals and agrochemicals.

Biological and pharmacological properties

Potential for study
The compound has been studied for its potential biological and pharmacological properties, indicating possible uses in medicine or agriculture.

InChI:InChI=1/C10H16Br2O/c1-9(2)5-10(3,4)8(12)6(13)7(9)11/h7-8H,5H2,1-4H3

Upstream product

• 14376-79-5 3,3,5,5-tetramethylcyclohexanone 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 

Downstream Products

• 60681-12-1 3,3,5,5-tetramethyl-cyclohexane-1,2-dione 
• 4694-11-5 2,2,4,4-tetramethylcyclopentanone 
• 20633-06-1 3,3,5,5-tetramethylcyclopentane-1,2-dione 
• 99177-50-1 3,3-dibromo-4,4,6,6-tetramethyl-cyclohexane-1,2-dione 
• 26167-29-3 2,3-dihydroxy-4,4,6,6-tetramethylcyclohex-2-enone 
• 33077-55-3 3-bromo-2-hydroxy-4,4,6,6-tetramethylcyclohex-2-enone 
• 32893-50-8 4,4,6,6-tetramethylcyclohexane-1,2,3-trione hydrate 
• 57744-39-5 4,4,6,6-tetramethylcyclohexane-1,2,3-trione 
• 64637-01-0 2-hydroxy-4,4,6,6-tetramethylcyclohex-2-enone 

Relevant articles and documents

Ene Reactions of Indane-1,2,3-trione (a Super-enophile) and Related Vicinal Tricarbonyl Systems

Indane-1,2,3-trione 1 is conveniently prepared in quantitative yield by the azeotropic drying of ninhydrin 2 using chlorobenzene as solvent.The central C=O group of the trione is extremely electrophilic and ene addition occurs at this site with a wide range of alkenes and with terminal alkynes in aprotic solvents at moderate temperatures (70-130 deg C).The reactivity of trione 1 is somewhat attenuated by the solvent, and the ene additions are consistently faster in chloroform than in tetrahydrofuran.Stereoselectivity, when relevant, appears largely to be dictated bysteric factors.Regiochemical control can be exercised if the ene contains two reaction sites.Isoprene and 2,4-dimethylpenta-1,3-diene, however, react by Diels-Alder rather than by ene addition; the adducts are the expected regioisomers 18 and 20, respectively.Attempts to catalyse the ene reactions with Lewis acids were unsuccessful.The analogous ene reactions of 4,4,5,5-tetramethyl-cyclopentane-1,2,3-trione 44, 4,4,6,6-tetramethylcyclohexane-1,2,3-trione 45, and 2,2-dimethyl-1,3-dioxane-4,5,6-trione ('oxo-Meldrum's acid') 46 were also briefly investigated.