| Customization: | Available |
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| CAS No.: | 80-15-9 |
| Formula: | C9h12o2 |
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Explore Cumyl Hydroperoxide (CHP), an oxidant commonly used in organic synthesis
Cumyl Hydroperoxide, known by its English name Cumyl Hydroperoxide, has a molecular formula of C9H12O2, a molecular weight of 152.19, a CAS number of 80-15-9, and aliases such as Cumene Hydroperoxide, CHP, and CMHP. It is an indispensable oxidant in chemical reactions.
CHP has a melting point of 44-45°C at room temperature, a boiling point of 100-101°C/8 mmHg (1066.6 Pa), a density of 1.030 g/cm3, and a flash point of 56°C. It is soluble in most organic solvents, only a trace amount is soluble in water, and exhibits unique physical properties.
From large international reagent manufacturers, you can buy 80% CHP cumene solution, a colorless or light yellow liquid. Under laboratory conditions, it can be prepared by directly oxidizing cumene with air at 105-115°C and high pressure. However, due to its potential explosiveness, high-purity CHP should be stored in a cool place away from acids, reducing substances and transition metals, and should be treated with a weak reducing agent to remove excess reagents after the reaction.
CHP is very useful as an oxidant in organic synthesis. It is often used in the epoxidation of olefins and the conversion of thioethers to sulfoxides or sulfones. CHP can also initiate oxidation reactions for some electron-rich aromatic compounds, such as furan. Especially in the field of asymmetric oxidation, such as the Sharpless epoxidation reaction, CHP can sometimes provide better product quality and stereoselectivity compared with TBHP, such as the superior catalytic performance in the reaction of allyl alcohol and methylallyl alcohol.
Compounds with chiral sulfoxide structures, such as omeprazole, have attracted much attention due to their biological activity. Studies have found that CHP can efficiently oxidize thioethers to form chiral sulfoxides under the catalysis of chiral titanium catalysts, and can also form stereoselective coordination with optically pure amino alcohols, showing excellent stereo control.
Under the action of metal catalysts such as Mo(CO)6, CHP can convert electron-rich furan into unsaturated carboxylic acids, and the addition of sodium carbonate can also change the configuration of the product olefin. For α,β-unsaturated carbonyl compounds, CHP can not only undergo epoxidation, but also induce 1,4-addition. Through chiral primary amine catalysts derived from cinchona alkaloids and temperature regulation, the reaction selectivity can be precisely controlled to generate chiral β-hydroxyketones and peroxide bonds.
In general, as a versatile oxidant, cumene hydroperoxide (CHP) is widely and finely used in organic synthesis, showing endless possibilities in chemical reactions. Understanding and mastering its characteristics will undoubtedly provide chemists with powerful tools to promote innovation in the field of chemistry.
| Density | 1.1±0.1 g/cm3 |
| Boiling point | 225.1±0.0 °C at 760 mmHg |
| Melting point | -30 °C |
| Molecular formula | C9H12O2 |
| Molecular weight | 152.19 |
| Flash point | 56.1±0.0 °C |
| Exact mass | 152.083725 |
| PSA | 29.46 |
| LogP | 2.63 |
| Appearance | Slightly yellow liquid |
| Vapor density | 5.4 (vs air) |
| Vapor pressure | 0.1±0.4 mmHg at 25°C |
| Refractive index | 1.515 |
| Storage conditions | This product should be sealed and stored in a cool, dark place. |
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