3-Hydroxy-2-naphthoic acid

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
CAS Number	92-70-6;
3D model (JSmol)	Interactive image;
Beilstein Reference	744100
ChEBI	CHEBI:80383;
ChEMBL	ChEMBLCHEMBL229301;
ChemSpider	6837;
ECHA InfoCard	100.001.983
EC Number	202-180-8;
KEGG	C16212;
PubChem CID	7104;
RTECS number	QL1755000;
UNII	C7S9D784HX;
CompTox Dashboard (EPA)	DTXSID3026560 ;
	InChI 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;
	SMILES C1=CC=C2C=C(C(=CC2=C1)C(=O)O)O;
Properties
Chemical formula	C11H8O3
Molar mass	188.182 g·mol−1
Appearance	Yellow solid
Melting point	222 °C (432 °F; 495 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H317, H319, H361, H371, H412
Precautionary statements	P201, P202, P260, 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). 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

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]

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

2-Hydroxy-1-naphthoic acid

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 (ed.). High Performance Pigments. John Wiley & Sons. p. 135. ISBN 978-3-527-62692-2.

[Ullmann-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.

[3] 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.

[4] Hans-Joachim Metz, Frank Morgenroth (2009). "Benzimidazolone Pigments and Related Structures". In Edwin B. Faulkner, Russell J. Schwartz (ed.). High Performance Pigments. John Wiley & Sons. p. 135. ISBN 978-3-527-62692-2.

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