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] I

References

^ Gilman, Henry; St. John, Nina B.; Schulze., F. (1931). "α-Naphthoic Acid". Organic Syntheses. 11: 80. doi:10.15227/orgsyn.011.0080.
^ 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.

[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.

[1]

[2]

Synthesis and reactions

See also

References