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 pictograms
GHS Signal word	Warning
GHS hazard statements	H302, H312, H317, H319, H361, H371, H402, H412
GHS precautionary statements	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 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 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

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

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