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3-Hydroxy-2-naphthoic acid

From Wikipedia, the free encyclopedia

3-Hydroxy-2-naphthoic acid
Names
Preferred IUPAC name
3-Hydroxynaphthalene-2-carboxylic acid
Other names
3-Hydroxy-2-naphthoic acid
BON acid
β-Hydroxynaphthoic acid
Identifiers
3D model (JSmol)
744100
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.983 Edit this at Wikidata
EC Number
  • 202-180-8
KEGG
RTECS number
  • QL1755000
UNII
  • InChI=1S/C11H8O3/c12-10-6-8-4-2-1-3-7(8)5-9(10)11(13)14/h1-6,12H,(H,13,14)
    Key: ALKYHXVLJMQRLQ-UHFFFAOYSA-N
  • C1=CC=C2C=C(C(=CC2=C1)C(=O)O)O
Properties
C11H8O3
Molar mass 188.182 g·mol−1
Appearance Yellow solid
Melting point 222 °C (432 °F; 495 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
GHS08: Health hazard
Warning
H302, H312, H317, H319, H361, H371, H412
P201, P202, P260, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P309+P311, P312, P321, P322, P330, P333+P313, P337+P313, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3-Hydroxy-2-naphthoic acid is an organic compound with the formula C10H6(OH)(CO2H). It is one of the several hydroxynaphthoic acids. It is a precursor to some azo dyes and pigments. It is prepared by carboxylation of 2-naphthol by the Kolbe–Schmitt reaction.[1]

Reactions

Lithol Rubine BK is one of many dyes made from 3-hydroxy-2-naphthoic acid. Notice that the coupling occurs adjacent to the hydroxy group.

3-Hydroxy-2-naphthoic acid is a precursor to many anilides, such as Naphthol AS, which are reactive toward diazonium salts to give deeply colored azo compounds. Azo coupling of 3-hydroxy-2-naphthoic acid gives many dyes as well. Heating 3-hydroxy-2-naphthoic acid in ammonia give 3-amino-2-naphthoic acid.[2]

Stub icon

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Related compounds

References

  1. ^ Gerald Booth (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009. ISBN 9783527303854.
  2. ^ Allen, C. F. H.; Bell, Alan (1942). "3-Amino-2-Naphthoic Acid". Organic Syntheses. 22: 19. doi:10.15227/orgsyn.022.0019.
This page was last edited on 14 April 2024, at 15:27
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