5,5-dimethylcyclohexane-1,3-dione

• ChemBase ID: 91841
• Molecular Formular: C8H12O2
• Molecular Mass: 140.17968
• Monoisotopic Mass: 140.08372962
• SMILES: O=C1CC(=O)CC(C1)(C)C
• Canonical SMILES: O=C1CC(=O)CC(C1)(C)C
• InChI: InChI=1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3
• InChIKey: BADXJIPKFRBFOT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,5-dimethylcyclohexane-1,3-dione
• IUPAC Traditional name: medon
• Synonyms: Dimedone; Methone; 5,5-Dimethylcyclohexane-1,3-dione 98%; 5,5-Dimethyl-1,3-cyclohexanedione; DIMEDONE; 5,5-Dimethyl-1,3-cyclohexanedione; 5,5-dimethylcyclohexane-1,3-dione; Cyclomethone; Dimethyldihydroresorcinol; Dimedone; 双甲酮; 醛试剂; 5,5-二甲基-1,3-环己二酮; 双甲酮

Database IDs

• CAS Number: 126-81-8
• EC Number: 204-804-4
• MDL Number: MFCD00001588
• Beilstein Number: 471489
• Merck Index: 143242
• PubChem SID: 162078539; 24893475; 24864009
• PubChem CID: 31358
• Chemspider ID: 29091
• Wikipedia Title: Dimedone

CALCULATED PROPERTIES

• Acid pKa: 7.504177
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.4036998
• LogD (pH = 7.4): 1.156143
• Log P: 1.4079771
• Molar Refractivity: 37.9643 cm^3
• Polarizability: 14.890126 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow crystals
• Melting Point: 142-151°C; 146-148 °C(lit.); 146-150°C; 146-151°C; 147–150 °C (decomposes)
• Boiling Point: 164-166°C

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Irritant/Light Sensitive
• RTECS: GV0345000
• German water hazard class: 2
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0%; ≥99.0% (GC); 95%; 98%
• Grade: for HPLC derivatization
• Quality: for the determination of aldehyde formaldehyde
• Linear Formula: (CH3)2C6H6(=O)2

DETAILS

MP Biomedicals - 02101594

Crystalline

Sigma Aldrich - D153303

Application
Part of furannulation strategy for the synthesis of naturally occurring fused 3-methylfurans.1
Packaging
25, 100 g in poly bottle

REFERENCES

• Classical reagent for the identification and isolation of aldehydes: J. Org. Chem., 11, 95 (1946).
• A comparative study has shown that CAN is superior to Mn(OAc)₃ for this type of reaction: J. Chem. Soc., Perkin 1, 1487 (1996).
• For conditions leading to exclusive 2-monomethylation, see: Synth. Commun., 3, 347 (1973). For direct nitration at the 2-position, see review on ɑ-nitroketones: Synthesis, 261 (1980).
• Undergoes an example of an oxidative addition of 1,3-dicarbonyl compounds, mediated by CAN (Cerium(IV) ammonium nitrate, A12882), to give an alkene, e.g. with 2-methyl-2-pentene, the product is a fused dihydrofuran derivative: J. Chem. Soc., Perkin 1, 187 (1995):