1-Hydroxy-2-naphthoic acid
Basic information
- CAS
86-48-6- Standard SMILES
O=C(O)c1ccc2ccccc2c1O- InChIKey
SJJCQDRGABAVBB-UHFFFAOYSA-N- Molecular formula
- C11H8O3
- Average molar mass
- 188.18 g/mol
- Monoisotopic mass
- 188.04734411
Overview
1-hydroxy-2-naphthoic acid is a naphthoic acid with the carboxy group at position 2 and carrying a hydroxy substituent at the 1-position. It is a xenobiotic metabolite produced by the biodegradation of phenanthrene by microorganisms. It has a role as a fungal xenobiotic metabolite and a bacterial xenobiotic metabolite. It is a member of naphthols, a naphthoic acid and a hydroxy monocarboxylic acid. It is functionally related to a 2-naphthoic acid. It is a conjugate acid of a 1-hydroxy-2-naphthoate.
Names & identifiers
- Preferred name
- 1-Hydroxy-2-naphthoic acid
- IUPAC
- 1-hydroxynaphthalene-2-carboxylic acid
- English name
- 1-Hydroxy-2-naphthoic acid
- Molecular formula
- C11H8O3
- Molecular weight
- 188.18
Names & synonyms
1-Hydroxy-2-naphthoic acid86-48-61-hydroxynaphthalene-2-carboxylic acid1-Naphthol-2-carboxylic acid2-Carboxy-1-naphtholXinafoic acid2-Naphthalenecarboxylic acid, 1-hydroxy-1-HYDROXY-2-NAPHTHALENECARBOXYLIC ACIDU8LZ3R07L8DTXSID5058937NSC-3717CHEBI:36108
Show more names
NSC 3717Xinafoic acid.RARECHEM AL BE 03591-Hydroxy-2-naphthoiLABOTEST-BB LT004527571-Hydroxy-2-phthoic acidhydroxy-2-naphthoic acid1-Hydroxy-2-naphthoicaci1-hydroxy-β-naphthoic acid
RefChem:433115DTXCID0048503201-674-02-Naphthoic acid, 1-hydroxy-CARBOXYNAPHTHOLMFCD00003960alpha-Hydroxynaphthoic acidCHEMBL229299
Database identifiers
- CAS
86-48-6
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 227
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Naphthoic Acids
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Physical DescriptionWhite to reddish solid; [Merck Index] Light brown powder; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 195 · 195-200 °C (dec.) (lit.)
- Boiling point
- 283.17 °C · 283.17°C (rough estimate)
- Density
- 1.21 · 1.2100 (rough estimate)
- refractive index
- 1.631 · 1.6310 (estimate)
- Flash point
- 150 °C · 150 °C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- alcohol: freely soluble
- form
- Powder or Crystals
- pka
- 3.02 · 3.02±0.30(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 7.1% (12 of 168) of reports.
Danger
H302 (61.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 168 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Naphthalenecarboxylic acid, 1-hydroxy-
1-Hydroxy-naphthalene-2-carboxylic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and strong eye irritant; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (61.9%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29182910
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
Chemistry & industry
Uses & manufacturing
UsesUsed as a reagent in synthetic organic chemistry; [Merck Index]
General Manufacturing Information2-Naphthalenecarboxylic acid, 1-hydroxy-: ACTIVE
Applications
UsesMetabolite from phenanthrene degradation. 1-Hydroxy-2-naphthoic acid is used as an intermediate for azo and triphenylmethane dyes and, more recently, for color-film dyes.
UsesIt is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.
General Description1-Hydroxy-2-naphthoic acid is produced by the transformation of phenanthrene by NCIB 9816 clones.
Preparation methods
PreparationTreatment of the dried sodium salt of 1-naphthol with carbon dioxide at 135℃ under pressure gives an 80 % yield of product.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
87 records
Compound notes
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