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