1-Naphthoic acid

1-Naphthoic acid

Names
Preferred IUPAC name Naphthalene-1-carboxylic acid
Other names 1-Naphthylenecarboxylic acid α-Naphthoic acid
Identifiers
CAS Number	86-55-5
3D model (JSmol)	Interactive image
Beilstein Reference	1908896
ChEBI	CHEBI:36466
ChEMBL	ChEMBL1160
ChemSpider	6586
ECHA InfoCard	100.001.529
EC Number	201-681-9
Gmelin Reference	28651
KEGG	C14091
PubChem CID	6847
UNII	2NIV4O66BH
CompTox Dashboard (EPA)	DTXSID50861668
InChI InChI=1S/C11H8O2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H,12,13) Key: LNETULKMXZVUST-UHFFFAOYSA-N
SMILES C1=CC=C2C(=C1)C=CC=C2C(=O)O
Properties
Chemical formula	C11H8O2
Molar mass	172.183 g·mol−1
Appearance	White solid
Melting point	161 °C (322 °F; 434 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1-Naphthoic acid is an organic compound with the formula C₁₀H₇CO₂H. It is one of two isomeric monocarboxylic acids of naphthalene, the other one being 2-naphthoic acid. In general the hydroxynaphthoic acids are more widely used than the parent naphthoic acids.

Synthesis and reactions

1-Naphthoic acid can be prepared by carboxylation of the Grignard reagent generated from 1-bromonaphthalene. ^[1]

1-Naphthoic acid is a substrate for C-H activation reactions. ^[2]

Catalytic hydrogenation of 1-Naphthoic acid gives 1,2,3,4-Tetrahydro-1-naphthoic acid [1914-65-4]. This is used in the synthesis of Tetryzoline.

See also

• Hydroxynaphthoic acids
• Classes of synthetic cannabinoids
  • Naphthoylindoles, or 3-(1-naphthoyl)indoles
  • Naphthoylpyrroles, or 3-(1-naphthoyl)pyrroles
• Natural products containing 1-naphthoic acid moiety
  • Neocarzinostatin (as 2-hydroxy-7-methoxy-5-methyl-1-naphthoate)
  • Azinomycin B (as 3-methoxy-5-methyl-1-naphthoate)

References

1. Gilman, Henry; St. John, Nina B.; Schulze., F. (1931). "α-Naphthoic Acid". Organic Syntheses. 11: 80. doi:10.15227/orgsyn.011.0080.
2. Mochida, Satoshi; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro (2011). "Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group". The Journal of Organic Chemistry. 76 (9): 3024–3033. doi:10.1021/jo200509m. PMID   21438629.