Valerophenone

Abstract

Valerophenone, also known as pentanophenone, is an aromatic ketone where a benzene ring is substituted with a pentanoyl group. This compound serves as a vital precursor in the synthesis of a-PVP, a stimulant drug. The present document offers a thorough exploration of Valerophenone, physical and chemical properties, relevant chemical information, various synthesis techniques, closing statements, and a comprehensive bibliography.

General Information About Valerophenone

Other synonyms names of Valerophenone are: Butyl phenyl ketone; Pentanophenone; 1-Phenyl-1-pentanone; 2-propylacetophenone; 1-phenyl-pentan-1-one; 4-methyl butyrophenone

• IUPAC Name of Valerophenone: 1-phenylpentan-1-one
• CAS number is 1009-14-9
• Trade name is Valerophenone

Physico-Chemical Properties of Valerophenone

• Molecular Formula C₁₁H₁₄O

• Molar Weight 162.23 g/mol

• Boiling point 244-245 °C

• Melting Point -9 and -9.4 °C

• Refraction index 1.5143

• Density 0.975-0.978 g/mL

• Solubility: in water 137.3 mg/L at 25 °C; soluble in organic solvents

• Color/Form: colourless liquid; light yellow

Structural formula of Valerophenone

Liquid Valerophenone In a Flask

Valerophenone Chemical Data

Valerophenone, a compound characterized by a benzene ring substituted with a pentanoyl group, is a derivative of trifluoroacetic acid (TFA) that serves as a potent antagonist for the histamine H1 receptor. Its binding to receptor cells effectively hinders the action of histamine, resulting in the inhibition of additional mediators like prostaglandins and leukotrienes. Notably, Valerophenone demonstrates remarkable inhibitory effects on polymerase chain reactions (PCR), chemiluminescent reactions, and analytical methods employing constant pressure. Additionally, it hampers the formation of substrate films, thereby potentially increasing light emission in chemiluminescent reactions. Studies have established Valerophenone’s efficacy as an inhibitor of human recombinant histamine H1 receptors, particularly at concentrations below 10 μM. This inhibition is believed to be attributed to the compound’s ability to form intramolecular hydrogen bonds with the hydroxyl group located at C-5 on the benzene ring. Furthermore, Valerophenone acts as an inhibitor of the enzyme carbonyl reductase.

Valerophenone Chemical reactions

Alpha-bromination of ketones occurs by the addition of molecular bromine (Br2) or bromine compounds to the alpha-position of the ketone group, forming alpha-bromoketones. The reaction can be performed in the presence of catalytic amounts of other substances, such as acids or Lewis acids, which help activate the bromine and provide regioselectivity to the reaction. Alpha-bromoketones are important intermediates in organic synthesis. They can serve as starting materials for further transformations, such as acylation, aldol condensation, and other reactions that lead to the formation of complex molecular structures.

Alpha-bromination

a-PVP Synthesis From 2-Bromovalerophenone

Synthesis of Valerophenone

Valerophenone, also known as 1-phenyl-1-pentanone, is commonly prepared by the acylation of benzene using valeryl chloride through a reaction known as the Friedel-Crafts acylation.

In the Friedel-Crafts acylation, benzene acts as a nucleophile and reacts with valeryl chloride in the presence of a Lewis acid catalyst, typically aluminum chloride (AlCl3) or ferric chloride (FeCl3). The Lewis acid activates the valeryl chloride by forming a complex with it, making it more reactive towards benzene. The benzene molecule then attacks the electrophilic carbonyl carbon of the valeryl chloride, leading to the substitution of a hydrogen atom in benzene with the valeryl group. The reaction proceeds through a series of steps, involving the formation of a carbocation intermediate and subsequent rearrangement. The final product of the reaction is valerophenone, where the valeryl group is attached to the benzene ring.

General scheme of Valerophenone synthesis

Conclusion

Valerophenone is a typical representative of aromatic ketones, displaying all the characteristic properties of ketones. Moreover, valerophenone can serve as a precursor for the synthesis of a-PVP (alpha-pyrrolidinopentiophenone) via 2-bromovalerophenone. By employing appropriate reaction conditions and reagents, valerophenone can be transformed into a-PVP, which is a derivative of valerophenone. It is also worth noting that valerophenone can be a derivative of trifluoroacetic acid (TFA). In summary, valerophenone is an important and useful compound in organic chemistry that can be utilized for the synthesis of various compounds, including a-PVP, through appropriate chemical transformations and reactions.

Bibliography

1. https://en.wikipedia.org/wiki/Valerophenone

2. https://pubchem.ncbi.nlm.nih.gov/compound/66093

3. https://www.chemspider.com/Chemical–Structure.59482.html

4. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:36812

5. https://www.biosynth.com/p/FV173268/1009-14-9-valerophenone

6. https://en.wikipedia.org/wiki/Alpha–Pyrrolidinopentiophenone

7. https://bbgate.com/media/%CE%B1-pvp–mdpv–synthesis–from-2-bromovalerophenone.47/

8. https://bbgate.com/threads/alpha–pvp–synthesis-1-10kg–scale–complete–video–tutorial.12/

9. https://en.wikipedia.org/wiki/Pyrrolidine

10. Milstein, D.; Stille, J. K. A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium. Journal of the American Chemical Society, 1978, 100, 11, pp. 3636–3638. doi:10.1021/ja00479a077 https://pubs.acs.org/doi/abs/10.1021/ja00479a077

11. https://en.wikipedia.org/wiki/Pentanoyl_chloride