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HomeProduct name list1-Hydroxy-2-naphthoic acid

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
1-Hydroxy-2-naphthoic acid Structural

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)
ghs
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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