21428-65-9

Basic information

• Product Name: 1,3-Cyclohexanedione, 2,2-dibromo-5,5-dimethyl-
• Synonyms: 3,3-dibromo-5,5-dimethylcyclohexa-1,3-dione;Dibromdimethyldihydroresorcin;MFVLTURDATWEKO-UHFFFAOYSA;2,2-dibromo-5,5-dimethyl-1,3-cyclohexanedione;2,2-Dibrom-5,5-dimethyl-cyclohexan-1,3-dion;2,2-dibromo-5,5-dimethyl cyclohexane-1,3-dione;1,3-Cyclohexanedione,2,2-dibromo-5,5-dimethyl
• CAS NO: 21428-65-9
• Molecular Formula: C8H10Br2O2
• Molecular Weight: 297.974
• Mol File: 21428-65-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 148-149 °C
• Boiling Point: 289.1±40.0 °C(Predicted)
• Density: 1.805±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,3-Cyclohexanedione, 2,2-dibromo-5,5-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclohexanedione, 2,2-dibromo-5,5-dimethyl-(21428-65-9)
• EPA Substance Registry System: 1,3-Cyclohexanedione, 2,2-dibromo-5,5-dimethyl-(21428-65-9)

Safety Data

• Hazardous Substances Data: 21428-65-9(Hazardous Substances Data)

Upstream product

• 1195-91-1 2-bromodimedone 
• 126-81-8 dimedone 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 873-95-0 1-amino-5,5-dimethylcyclohexen-3-one 
• 37722-34-2 2-bromo-5,5-dimethyl-3-hydroxycyclohex-2-en-1-one 
• 4683-45-8 3-methoxy-5,5-dimethyl-cyclohex-2-enone 
• 3471-13-4 dimedone 

Downstream Products

• 586-77-6 4-bromo-N,N-dimethylaniline 
• 92898-24-3 2-phenyl-3-methyl-4-oxo-6,6-dimethyl-2,3,4,5,6,7-hexahydrobenzofuran 
• 37722-34-2 2-bromo-5,5-dimethyl-3-hydroxycyclohex-2-en-1-one 
• 18150-87-3 6,6-dimethyl-4-oxo-2-phenyl-4,5,6,7-tetrahydrobenzofuran 
• 1116649-51-4 1,1-dicyano-6,6-dimethyl-2-phenylspiro[2.5]octane-4,8-dione 
• 1195-91-1 2-bromodimedone 
• 822-85-5 α-bromocyclohexanone 
• 21428-80-8 2,2,4,4-Tetrabrom-dimedon 
• 21428-82-0 2,4,4-Tribrom-dimedon 
• 21428-74-0 2,6-dibromo-5,5-dimethyl-3-methoxycyclohex-2-en-1-one 

Relevant articles and documents

Efficient synthesis of some novel spiro heterocycles containing thiazole, oxazole, thiadiazole and triazolo-thiadiazole moiety under microwave irradiation

5,5-Dimethyl cyclohexane-1,3-dione 1 was treated with twice the molar quantity of bromine in glacial acetic acid to yield 2,2-dibromo-5,5-dimethyl cyclohexane-1,3-dione 2. The dibromo compound 2 was subjected to reaction with substituted 2-aminothiophenol

Production mechanism of active species on the oxidative bromination following perhydrolase activity

Hypobromous acid and molecular bromine have been described as the active species involved in the oxidative bromination using perhydrolase, which catalyzes the reaction from acetic acid and hydrogen peroxide to peracetic acid (AcOOH). However, the brominating activity of them in a chemical model system was lower than that of the active species produced by the spontaneous reaction between AcOOH and Br-. Consequently, acetyl hypobromite (AcOBr) was suggested as new active species on the bromination by detection of the decarboxylation in the reaction between AcOOH and Br- and the strong brominating power with some tolerance against H2O2. Its production mechanism was explained as the ionic reaction involving the protonated intermediate of AcOOH by kinetic analysis.

Solvent-free bromination reactions with sodium bromide and oxone promoted by mechanical milling

New solvent-free brominations of 1,3-dicarbonyl compounds, phenols, various alkenes including chalcones, azachalcones, 4-phenylbut-3-en-2-one, methyl cinnamate, styrene and 1,3-cyclohexadiene were efficiently achieved by employing sodium bromide and oxone under mechanical milling conditions. The brominated products were obtained in good to excellent yields.