Shandong Huashang Chemical Co., Ltd. is a high-tech enterprise specializing in the research and development, manufacturing, and sales of fine chemicals. Headquartered in Jinan, Shandong, China, we are committed to delivering high-quality products to our global partners. Currently, over 90% of our products are exported to developed markets, including North America, Europe, Japan, South Korea, and the Middle East.
Product Description
Dimedone (CAS: 126-81-8), also known as 5,5-Dimethyl-1,3-cyclohexanedione or Methone, is a high-purity cyclic β-diketone with a cyclohexane core. It appears as a white to off-white or light yellow-green crystalline solid, featuring two carbonyl groups (-CO-) at the 1- and 3-positions and two methyl groups (-CH?) at the 5-position. Characterized by good chemical stability, light sensitivity, and tautomeric equilibrium (keto-enol form) in solution, it is soluble in water, ethanol, methanol, chloroform, and benzene. Synthesized mainly via the reaction of mesityl oxide and diethyl malonate, it is a versatile reagent and intermediate widely used in organic synthesis, analytical chemistry, and pharmaceutical research.
Uses
Analytical Chemistry: A classic and specific reagent for the qualitative and quantitative detection, separation, and identification of aldehydes, as it reacts with aldehydes to form insoluble crystalline derivatives with distinct melting points (ketones do not react with it).
Organic Synthesis: Key building block for synthesizing various organic compounds, including monastrol analogues, anti-HBV active tetrahydroquinazolinone derivatives, and 3-methylfuran derivatives; also serves as a catalyst for piperidine synthesis.
Pharmaceutical Research: Used in the research and development of pharmaceutical intermediates, particularly in the synthesis of compounds with biological activities such as anti-HBV properties.
Laboratory Research: Commonly used chemical reagent in organic chemistry, analytical chemistry, and biochemistry laboratories for reaction optimization, structural identification, and scientific research experiments.
Molecular Formula & Structure
- Molecular Formula: C?H??O?
- Molecular Weight: 140.18 g/mol
- IUPAC Name: 5,5-Dimethylcyclohexane-1,3-dione
- Synonyms: 5,5-Dimethyl-1,3-cyclohexanedione; Methone; Cyclomethone; 5,5-Dimethyl dihydro resorcinol; 1,1-Dimethyl-3,5-cyclohexanedione; MFCD00001588; InChIKey: BADXJIPKFRBFOT-UHFFFAOYSA-N; Beilstein: 471489; EC: 204-804-4.
- CAS Number: 126-81-8
- SMILES Code: O=C1CC(=O)CC(C)(C)C1
- Chemical Structure: A cyclic diketone with a cyclohexane core, with two carbonyl groups at the 1- and 3-positions and two methyl groups substituted at the 5-position. It exists in tautomeric equilibrium between keto and enol forms in solution (2:1 keto-enol ratio in chloroform), and in crystalline state, it forms chains of enol-form molecules linked by hydrogen bonds.
Physical & Chemical Properties
- Appearance: White to off-white or light yellow-green needle-like or prismatic crystals; odorless; no visible impurities; sensitive to light.
- Melting Point: 147–151°C (lit., decomposes); Boiling Point: Not clearly reported; Density: Not clearly reported; Flash Point: Not clearly reported; pKa: 4.8 (at 25°C).
- Solubility: Soluble in water (0.416 g/100 ml at 25°C), ethanol, methanol, chloroform, benzene, acetone, and 50% ethanol-water mixture; aqueous solution is prone to oxidation when exposed to light and air, and also oxidizes when stored in the dark for a long time.
- Stability: Stable under normal temperature and pressure; sensitive to light; dry crystals can be stored stably for several years in brown bottles at room temperature; avoid prolonged exposure to light and high temperature.
- Toxicity & Safety: Low acute toxicity; slightly irritating to skin and eyes; no known carcinogenic or mutagenic effects; handle with caution to avoid inhalation, skin, and eye contact; GHS Labeling: No special hazardous labeling (low risk).
Synthesis & Storage
- Synthesis: Mainly via base-catalyzed reaction of mesityl oxide and diethyl malonate, undergoing Michael addition, intramolecular Claisen condensation (Dieckmann cyclization), saponification, and decarboxylation reactions in sequence; the crude product is purified by recrystallization to obtain high-purity dimedone.
- Storage: Store at 10–15°C in a cool, dry, well-ventilated, dark warehouse; keep in sealed containers under inert atmosphere (nitrogen-filled) to prevent oxidation and moisture absorption. Packed in 25g, 100g, 500g, 1kg, or 5kg sealed brown glass bottles or plastic drums. Avoid direct sunlight, high temperature (>30°C), and contact with strong oxidants; keep away from food and feed. Shelf life: 24 months if unopened and stored properly.
- Handling Precautions: Use in well-ventilated areas; wear nitrile gloves and safety goggles to avoid skin and eye contact and inhalation of dust. In case of skin contact, rinse with plenty of water for 15 minutes; in case of eye contact, rinse with water for 15 minutes. Avoid generating dust; prevent release into the environment. Dispose of waste in accordance with local regulations; store in brown containers to avoid light exposure.
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