2-methylcyclopentane-1,3-dione

• ChemBase ID: 70284
• Molecular Formular: C6H8O2
• Molecular Mass: 112.12652
• Monoisotopic Mass: 112.0524295
• SMILES: C1(=O)C(C(=O)CC1)C
• Canonical SMILES: CC1C(=O)CCC1=O
• InChI: InChI=1S/C6H8O2/c1-4-5(7)2-3-6(4)8/h4H,2-3H2,1H3
• InChIKey: HXZILEQYFQYQCE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methylcyclopentane-1,3-dione
• IUPAC Traditional name: 2-methylcyclopentane-1,3-dione
• Synonyms: 2-Methyl-1,3-cyclopentanedione; 2-Methyl-1,3-cyclopentanedione; 2-Methyl-1,3-dioxocyclopentane; 2-Methylcyclopentane-1,3-dione; 2-Methylcyclopentane-1,3-dione; 2-甲基-1,3-环戊二酮; 2-甲基环戊烷-1,3-二酮

Database IDs

• CAS Number: 424823-07-4; 765-69-5
• EC Number: 212-153-2
• MDL Number: MFCD00001406
• Beilstein Number: 1237255
• PubChem SID: 24847313; 24884717; 162036007
• PubChem CID: 13005

CALCULATED PROPERTIES

• Acid pKa: 9.815537
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.9193077
• LogD (pH = 7.4): 0.9176768
• Log P: 0.9193285
• Molar Refractivity: 28.9141 cm^3
• Polarizability: 11.225105 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 212-215 °C (Lit.); 212-215 °C(lit.); 212-216°C; 213-215°C; 218 - 220°C
• Hydrophobicity(logP): 0.066

Safety Information

• Storage Warning: IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ACHE(43), BCHE(590), CES1(1066)

Product Information

• Purity: ≥98.0% (GC); 95%; 95+%; 98%; 99%
• Grade: purum
• Linear Formula: CH3C5H5(=O)2

DETAILS

Sigma Aldrich - 117021

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 66515

Other Notes
β-Diketone building block; review of its uses1

REFERENCES

• Valuable intermediate for steroid synthesis. For a review, see: Synthesis, 477 (1989). Condensation with methyl vinyl ketone and proline-catalyzed asymmetric aldol cyclization of the product gives a diketone useful in steroid and prostaglandin synthesis: Org. Synth. Coll., 7, 363 (1990):