1-Naphthoic acid

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
  • 201-681-9
28651
KEGG
UNII
  • 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
  • C1=CC=C2C(=C1)C=CC=C2C(=O)O
Properties
C11H8O2
Molar mass 172.183 g·mol−1
Appearance White solid
Melting point 161 °C (322 °F; 434 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
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).
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

See also

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.
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