2-Methylcyclopentane-1,3-dione

2-Methylcyclopentane-1,3-dione, with the CAS number 765-69-5 and molecular formula C₆H₈O₂, is a versatile organic compound classified under ketones and aldehydes. It has a well-documented molecular weight of 112.13 g/mol and is structurally characterized by a cyclopentane ring substituted with a methyl group and two carbonyl groups at the 1 and 3 positions, as reflected in its canonical SMILES notation: CC1C(=O)CCC1=O.
This compound is known by several synonyms in scientific and industrial contexts, including 2-methyl-1,3-cyclopentanedione, 1,3-cyclopentanedione, 2-methyl, and Methyl Cycle-D. It also has unique identifiers such as PubChem CID 13005, EINECS number 212-153-2, and UNII C9LG5VP01C.
In terms of structural properties, 2-Methylcyclopentane-1,3-dione exhibits interesting chemical behavior in the crystal state. Synchrotron X-ray diffraction studies have revealed that the molecule exists in the enol form and forms strong intermolecular O-H···O hydrogen bonds, which contribute to its stability and reactivity. These bonds connect molecules along the (001) direction in the crystal lattice, and deformation density maps confirm resonance within the O=C-C=C-OH fragment.
Historically, its utility has been explored in various synthetic chemistry fields, with early research focusing on its role as a building block for complex organic molecules. Its skeleton can be derived from the hydrogenation of cyclopentanol, linking its production to accessible starting materials. Today, it remains a staple in both academic research and specialized industrial synthesis due to its unique structural features.

Distinct Physical Characteristics: It presents as a white to light yellow solid, with a density of 1.33 g/cm³ and a boiling point of 213 °C, making it easy to identify and handle in laboratory settings.
Well-Defined Chemical Identity: Possesses clear structural confirmation via crystallographic studies, with documented resonance-assisted hydrogen bonds and enol-form stability, ensuring consistency in experimental applications.
Controlled Solubility Profile: Exhibits reliable solubility in common laboratory solvents—for instance, it dissolves at 100 mg/mL in DMSO (requiring sonication) and can be formulated into clear in vivo working solutions with combinations of DMSO, PEG 300, Tween 80, and saline.
Stable Under Specified Storage: Maintains integrity for extended periods when stored properly: 3 years at -20 °C (powder), 2 years at 4 °C (powder), and 6 months at -80 °C (in solvent), minimizing waste and ensuring long-term usability.

Steroid Synthesis: Serves as a key intermediate in the total synthesis of steroids and cardiotonic steroids, playing a pivotal role in constructing the core molecular framework of these biologically active compounds.
Enzyme Inhibitor Research: Used as a reactant in identifying and characterizing benzil analogues that act as inhibitors of mammalian carboxylesterases, supporting drug discovery and enzymology studies.
Terpene Synthesis: Applied in model synthetic studies for picrotoxane-type sesquiterpenes (e.g., tutin), aiding the stereoselective construction of cis-fused 5,6-ring skeletons critical to terpene structure.
Complex Molecule Construction: Acts as an efficient synthon for the synthesis of (±)-α-cuparenone, a naturally occurring compound with potential biological activity, demonstrating its value in natural product chemistry.
Charge-Density Analysis: Utilized as a model compound in crystallographic research to compare multipolar atom and spherical charge models, advancing understanding of molecular electron density distributions.

In the fields of synthetic organic chemistry, steroid synthesis, and enzymology research, customers interested in 2-Methylcyclopentane-1,3-dione often seek complementary compounds such as 1,3-Cyclopentanedione (the unsubstituted parent structure), Cyclopentanone (a simpler cyclic ketone building block), Benzil (diphenylethane-1,2-dione, used in inhibitor studies), and 3-Methylcyclohexane-1,2-dione (a homologous cyclic dione for structure-activity relationship investigations). These products share applications in intermediate synthesis, natural product preparation, and enzymology assays, aligning with the research goals supported by 2-Methylcyclopentane-1,3-dione. If you are interested in related products, you can directly contact us or inquire about product customization services.