1,3-Cyclohexanedione(1,3-CHD)
It is a colorless solid, m.p. 103～105°C, soluble in ethanol and other solvents.
1, 3-CHD is an intermediate in the herbicides nitrosulfamone, cyclosulfamone, sulfamone, and nitrososulfamone.
1,3-Cyclohexanedione (1,3-CHD) is a versatile cyclic diketone with applications in chemical synthesis, pharmaceuticals, and agrochemicals. It serves as a key intermediate in various organic transformations.
Chemical Characteristics
| Melting point | 101-105 °C (lit.) |
| Boiling point | 170.05°C (rough estimate) |
| density | 1,1 g/cm3 |
| vapor pressure | 0.018Pa at 25℃ |
| refractive index | 1.4576 (estimate) |
| storage temp. | Store at +2°C to +8°C. |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| pka | 5.26(at 25℃) |
| form | Powder |
| color | Pale yellow to beige |
| Water Solubility | soluble |
| Merck | 14,3178 |
| BRN | 385888 |
| LogP | 0.461 at 21.4℃ and pH3.2 |
| Surface tension | 69.9mN/m at 1.01g/L and 22℃ |
| CAS DataBase Reference | 504-02-9(CAS DataBase Reference) |
| NIST Chemistry Reference | 1,3-Cyclohexanedione(504-02-9) |
| EPA Substance Registry System | 1,3-Cyclohexanedione (504-02-9) |
Applications
Chemical Synthesis:
Precursor for the synthesis of heterocyclic compounds, including pyrazoles and isoxazoles.
Used in aldol condensation and Michael addition reactions.
Pharmaceutical Industry:
Intermediate in the development of drugs with anti-inflammatory and anti-cancer properties.
Key component in synthesizing compounds with biological activity.
Agrochemical Industry:
Building block for herbicides, fungicides, and plant growth regulators.
Dye and Pigment Industry:
Used in the synthesis of colorants and light-stable pigments.
Advantages
High reactivity due to keto-enol tautomerism.
Versatile applications in synthetic chemistry.
Stable under standard storage conditions.
Safety and Handling
Protective Measures:
Use gloves, goggles, and protective clothing when handling.
Work in a well-ventilated area or under a fume hood.
Storage:
Store in a cool, dry place away from heat, light, and moisture.
Keep the container tightly sealed to avoid contamination.
Hazards:
Inhalation: May cause respiratory irritation.
Skin Contact: Can cause mild irritation.
Eye Contact: Risk of irritation; avoid direct contact.
Ingestion: Harmful if swallowed; may cause gastrointestinal discomfort.
First Aid Measures:
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin Contact: Wash with soap and water; consult a doctor if irritation occurs.
Eye Contact: Rinse with water for at least 15 minutes; get medical help if irritation persists.
Ingestion: Rinse mouth; seek immediate medical care.
Conclusion
1,3-Cyclohexanedione (1,3-CHD) is a valuable intermediate with broad applications in pharmaceuticals, agrochemicals, and industrial chemistry. Its reactive properties make it indispensable for advanced organic synthesis.
FAQ
1. What is the primary use of 1,3-Cyclohexanedione?
It is widely used as a precursor in the synthesis of heterocyclic compounds and biologically active molecules.
2. Is it stable under normal conditions?
Yes, it is stable when stored in a cool, dry place away from moisture and heat.
3. Can it form enolates?
Yes, it readily forms enolates under basic conditions, enabling its use in aldol and Michael addition reactions.
4. Is it water-soluble?
It is slightly soluble in water but dissolves well in organic solvents like ethanol and acetone.
5. What safety precautions are necessary?
Handle with protective gear and ensure proper ventilation to avoid inhalation or contact hazards.
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