Chemistry:3-Hydroxy-2-naphthoic acid
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| Names | |
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| Preferred IUPAC name
3-Hydroxynaphthalene-2-carboxylic acid | |
| Other names
3-Hydroxy-2-naphthoic acid
BON acid β-Hydroxynaphthoic acid | |
| Identifiers | |
3D model (JSmol)
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| 744100 | |
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| Properties | |
| C11H8O3 | |
| Molar mass | 188.182 g·mol−1 |
| Appearance | Yellow solid |
| Melting point | 222 °C (432 °F; 495 K) |
| Hazards | |
| GHS pictograms |  
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| GHS Signal word | Warning |
| H302, H312, H317, H319, H361, H371, 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 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
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]
3-Hydroxy-2-naphthoic acid can be condensed with 4-amino-2-benzimidazolinone. The resulting amide is a precursor to commercial dyes and pigments via azo coupling.[3][4]
3-Hydroxy-2-naphthoic acid can be used to make Dynasore [304448-55-3].
Related compounds
References
- ↑ Gerald Booth (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009. ISBN 9783527303854.
- ↑ Allen, C. F. H.; Bell, Alan (1942). "3-Amino-2-Naphthoic Acid". Organic Syntheses 22: 19. doi:10.15227/orgsyn.022.0019.
- ↑ Jaffe, Edward E. (2004). "Pigments, Organic". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.151807011001060605.a01.pub2. ISBN 978-0-471-48494-3.
- ↑ Hans-Joachim Metz, Frank Morgenroth (2009). "Benzimidazolone Pigments and Related Structures". in Edwin B. Faulkner, Russell J. Schwartz. High Performance Pigments. John Wiley & Sons. p. 135. ISBN 978-3-527-62692-2. https://books.google.com/books?id=ecD6AuaJyFwC.
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