3-Hydroxy-2-naphthoic acid

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

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
EC Number
  • 202-180-8
KEGG
RTECS number
  • QL1755000
UNII
Properties
C11H8O3
Molar mass 188.182 g·mol−1
Appearance Yellow solid
Melting point 222 °C (432 °F; 495 K)
Hazards
GHS pictograms
GHS Signal word Warning
H302, H312, H317, H319, H361, H371, H402, H412
P201, P202, P260, P261, P264, P270, P272, P273, P280, P281, P301+312, P302+352, P305+351+338, P308+313, P309+311, P312, P321, P322, P330, P333+313, P337+313, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.

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.

References

  1. Gerald Booth (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009..
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