1-Naphthoic acid
Names | |
---|---|
Preferred IUPAC name Naphthalene-1-carboxylic acid | |
Other names 1-Naphthylenecarboxylic acid α-Naphthoic acid | |
Identifiers | |
3D model (JSmol) |
|
1908896 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.529 |
EC Number |
|
28651 | |
KEGG | |
PubChem CID |
|
UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
Properties | |
C11H8O2 | |
Molar mass | 172.183 g·mol−1 |
Appearance | White solid |
Melting point | 161 °C (322 °F; 434 K) |
Hazards | |
GHS labelling: | |
Warning | |
H315, H319, H335 | |
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). |
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
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
- ^ 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.