1-Naphthalenecarbonyl Chloride

1-Naphthalenecarbonyl Chloride

Abstract

1-Naphthoylchloride, featuring the functional group −C(=O)Cl, is a key component in numerous organic syntheses and plays a crucial role in the synthesis of JWH derivatives. This comprehensive article provides an extensive overview of 1-naphthoylchloride, covering its general information, physico-chemical properties, detailed chemical information, synthesis methods, insightful conclusions, and a comprehensive bibliography.

General Information About 1-naphthoylchloride

Other synonyms names of 1-naphthoylchloride are: 1-(Chlorocarbonyl)naphthalene; 1-Naphthalenecarbonyl chloride; 1-naphthalenecarboxylic acid chloride; 1-naphthaloylchloride; 1-Naphthoic acid chloride; 1-naphthylcarbonyl chloride; alpha-Naphthoyl chloride

• IUPAC Name of 1-naphthoylchloride: naphthalene-1-carbonyl chloride
• CAS number is 879-18-5

Physico-Chemical Properties of 1-naphthoylchloride

• Molecular Formula C₁₁H₇ClO

• Molar Weight 190.62 g/mol

Boiling points

• 118 °C / 0.1 mm (436.75 °C / 760 mmHg) Alfa Aesar

• 120 °C / 2 mmHg (335.9846 °C / 760 mmHg) Manchester Organics

• 190 °C / 35 mmHg OU Chemical Safety Data

• 118 °C / 0.1 mm (436.75 °C / 760 mmHg) Alfa Aesar

• 190 °C / 35 mmHg (322.1218 °C / 760 mmHg) Sigma-Aldrich

• 120 °C / 2 mm (335.9846 °C / 760 mmHg) Oakwood

Melting Points

• 16-19 °C Alfa Aesar

• 16-19 °C Manchester Organics

• 26 °C OU Chemical Safety Data

• 18 °C Jean-Claude Bradley

• 26 °C Jean-Claude Bradley

• 16-19 °C Alfa Aesar

• 16-19 °C Sigma-Aldrich

• 16-19 °C Oakwood

• Refraction index 1.6525 Alfa Aesar and 1.652 Sigma-Aldrich

• Density 1.265 g/mL Alfa Aesar and 1.265 g/mL Sigma-Aldrich

• Solubility: decomposes in water

• Color/Form: White, Liquid or Solid

• Safety and Handling: Danger!; Serious eye damage/eye irritation Category 1; Skin corrosion/irritation Category 1B; H318-Causes serious eye damage; H314-Causes severe skin burns and eye damage; Toxic Gases and Vapors, Acid Halides.

Structural formula of 1-naphthoylchloride

Liquid appearance of 1-naphthoylchloride

Chemical Information About 1-Naphthoylchloride

In the field of organic chemistry, an acyl chloride, also known as an acid chloride, refers to an organic compound that contains the functional group −C(=O)Cl. Its chemical formula is typically represented as R−COCl, where R represents a side chain. These compounds are considered reactive derivatives of carboxylic acids (R−C(=O)OH). Acyl chlorides constitute a significant subgroup within the category of acyl halides. Due to their inability to form hydrogen bonds, they exhibit lower boiling and melting points compared to similar carboxylic acids. Acyl chlorides with low molecular weight are often lachrymators, and they exhibit violent reactions when exposed to water, alcohols, and amines.

1-Naphthoyl chloride is a metabolite derived from 1-naphthol. It has found applications in the synthesis of steroidal alkaloids, including the anti-inflammatory drug indomethacin and the anesthetic ketamine. Moreover, 1-Naphthoyl chloride serves as a precursor in the production of synthetic cannabinoids, which are substances that mimic the effects of cannabis but are not derived from marijuana. These synthetic cannabinoids interact with receptors present on specific cells that are sensitive to cannabinoids. This binding leads to alterations in cellular function and can induce psychological effects such as paranoia and hallucinations.

Reactions involving 1-naphthoyl chloride:

When exposed to water, acyl chlorides undergo hydrolysis, resulting in the formation of the corresponding carboxylic acid and hydrochloric acid.

1-Naphthoylchloride Reaction With Water

The synthesis reaction of naphthoylindole, which is also employed in the synthesis of JWH derivatives. Figure 14.

1-Naphthoylchloride Reaction With Indole

Synthesis of 1-Naphthoylchloride

In laboratory settings, acyl chlorides are typically synthesized by treating carboxylic acids with thionyl chloride (SOCl₂). This reaction is catalyzed by dimethylformamide (DMF) and other additives. Thionyl chloride is an ideal reagent for this purpose due to the gaseous nature of its by-products (HCl, SO₂) and its low boiling point (76 °C), allowing easy removal of residual thionyl chloride. The catalytic role of DMF involves its reaction with oxalyl chloride to generate the Vilsmeier reagent, an iminium intermediate. This intermediate then reacts with the carboxylic acid, forming a mixed imino-anhydride. Through acyl substitution with the liberated chloride, the acid anhydride is formed, accompanied by the release of regenerated DMF. Oxalyl chloride, although more expensive than thionyl chloride, is a milder reagent, offering greater selectivity.

General Scheme of 1-Naphthoylchloride Synthesis

Making thionyl chloride

Conclusion

1-Naphthoyl chloride is a typical representative of acyl chlorides. It serves as a metabolite of 1-naphthol and finds application in various synthesis processes. Notably, it has been utilized in the synthesis of steroidal alkaloids, including well-known pharmaceuticals such as the anti-inflammatory drug indomethacin and the anesthetic ketamine. Furthermore, 1-naphthoyl chloride plays a crucial role in the synthesis of derivatives of JWH, which are compounds of interest due to their potential pharmacological properties. Its versatile reactivity and wide range of applications make 1-naphthoyl chloride a valuable compound in organic synthesis.

Bibliography

1. https://materials.springer.com/substanceprofile/docs/smsid_ybxmowrnpdxkkvxe

2. https://pubchem.ncbi.nlm.nih.gov/compound/1-Naphthoyl-chloride

3. https://en.wikipedia.org/wiki/Acyl_chloride

4. https://www.chemspider.com/Chemical-Structure.63334.html?rid=86ad3adf-4675-4cba-854b-dc9f8f4d6bb3

5. https://www.sigmaaldrich.com/UA/en/product/aldrich/250252

6. https://www.fishersci.co.uk/shop/products/1-naphthoyl-chloride-99-thermo-scientific/10409950

7. https://en.wikipedia.org/wiki/Vaska%27s_complex

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9. Martin Ansell (1972). “Preparation of acyl halides”. In Saul Patai (ed.). Acyl Halides. PATAI’S Chemistry of Functional Groups. pp. 35–68. doi:10.1002/9780470771273.ch2 https://onlinelibrary.wiley.com/doi/10.1002/9780470771273.ch2

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