1-Hydroxy-2-naphthoic acid
Synonym(s):α-Hydroxynaphthoic acid
- CAS NO.:86-48-6
- Empirical Formula: C11H8O3
- Molecular Weight: 188.18
- MDL number: MFCD00003960
- EINECS: 201-674-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-01 20:20:38
What is 1-Hydroxy-2-naphthoic acid?
Chemical properties
beige to brown-grey powder. 1-Hydroxy-2-naphthoic acid [86-48-6], C11H8O3, Mr 188.17, mp 200℃, is only sparingly soluble in hot water but readily soluble in alkali and ethanol. It couples with diazo compounds in the 4-position and, with excess, in the 4,7-positions. It is sulfonated by oleum to give the 4-sulfonic and then the 4,7-disulfonic acids. Halogenation occurs in the 4-position, and nitrosation gives 2-nitroso-1-naphthol.
The Uses of 1-Hydroxy-2-naphthoic acid
Metabolite from phenanthrene degradation.
The Uses of 1-Hydroxy-2-naphthoic acid
It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.
Definition
ChEBI: 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 bacterial xenobiotic metabolite and a fungal xenobiotic metabolite. It is a naphthoic acid, a member of naphthols 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.
Preparation
Treatment of the dried sodium salt of 1-naphthol with carbon dioxide at 135℃ under pressure gives an 80 % yield of product.
General Description
1-Hydroxy-2-naphthoic acid is produced by the transformation of phenanthrene by NCIB 9816 clones.
Purification Methods
Successively crystallise the acid from EtOH/water, diethyl ether and acetonitrile, with filtration through a column of charcoal and Celite. [Tong & Glesmann J Am Chem Soc 79 583 1957, Beilstein 10 H 331, 10 IV 1194.]
Properties of 1-Hydroxy-2-naphthoic acid
Melting point: | 195-200 °C (dec.) (lit.) |
Boiling point: | 283.17°C (rough estimate) |
Density | 1.2100 (rough estimate) |
refractive index | 1.6310 (estimate) |
Flash point: | 150 °C |
storage temp. | Sealed in dry,Room Temperature |
solubility | alcohol: freely soluble |
form | Powder or Crystals |
pka | 3.02±0.30(Predicted) |
color | White to slightly pink to tan |
Water Solubility | SOLUBLE IN HOT WATER |
Merck | 14,4834 |
BRN | 974438 |
CAS DataBase Reference | 86-48-6(CAS DataBase Reference) |
EPA Substance Registry System | 1-Hydroxy-2-naphthoic acid (86-48-6) |
Safety information for 1-Hydroxy-2-naphthoic acid
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 1-Hydroxy-2-naphthoic acid
InChIKey | SJJCQDRGABAVBB-UHFFFAOYSA-N |
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