ChemicalBook > CAS DataBase List > 1-Naphthol

1-Naphthol

Product Name
1-Naphthol
CAS No.
90-15-3
Chemical Name
1-Naphthol
Synonyms
naphthalen-1-ol;1-naphthalenol;1-HYDROXYNAPHTHALENE;ALPHA-NAPHTHOL;α-Naphthol;α-Naphthol;1-naphtol;ALPHA-NAPTHOL;furro er;Oxidation base 33
CBNumber
CB0279325
Molecular Formula
C10H8O
Formula Weight
144.17
MOL File
90-15-3.mol
More
Less

1-Naphthol Property

Melting point:
94-96 °C(lit.)
Boiling point:
278-280 °C(lit.)
Density 
1.224
vapor density 
4.5 (120 °C, vs air)
vapor pressure 
1 mm Hg ( 94 °C)
refractive index 
1.6224
Flash point:
125 °C
storage temp. 
Store below +30°C.
solubility 
Soluble in benzene, chloroform, ether and ethanol.
pka
9.34(at 25℃)
form 
Crystalline Flakes
color 
white to off-white
Odor
Slight phenolic odor
explosive limit
5%
Water Solubility 
436.7mg/L(25 ºC)
λmax
324nm(MeOH)(lit.)
Sensitive 
Air & Light Sensitive
Merck 
14,6383
BRN 
1817321
Stability:
Stable, but air and light sensitive - store under inert gas. Incompatible with strong bases, strong oxidizing agents.
InChIKey
KJCVRFUGPWSIIH-UHFFFAOYSA-N
LogP
2.84 at 25℃
CAS DataBase Reference
90-15-3(CAS DataBase Reference)
NIST Chemistry Reference
1-Naphthalenol(90-15-3)
EPA Substance Registry System
1-Naphthol (90-15-3)
More
Less

Safety

Hazard Codes 
Xn,N
Risk Statements 
21/22-37/38-41-51/53
Safety Statements 
22-26-37/39-2-61
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
1
RTECS 
QL2800000
8-23
Autoignition Temperature
510 °C
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
III
HS Code 
29071510
Hazardous Substances Data
90-15-3(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 1870 mg/kg LD50 dermal Rabbit 880 mg/kg
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H311Toxic in contact with skin

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H335May cause respiratory irritation

H371May cause damage to organs

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
N1000
Product name
General Purpose Viscosity Standard; UKAS ISO/IEC17025 and ISO 17034 certified
Purity
viscosity 2610?mPa.s?(25?°C)
Packaging
500ML
Price
$180
Updated
2024/03/01
Sigma-Aldrich
Product number
8.22289
Product name
1-Naphthol
Purity
for synthesis
Packaging
250g
Price
$51.8
Updated
2024/03/01
Sigma-Aldrich
Product number
8.22289
Product name
1-Naphthol
Purity
for synthesis
Packaging
1kg
Price
$158
Updated
2024/03/01
Sigma-Aldrich
Product number
33420
Product name
1-Naphthol
Purity
puriss. p.a., reag. Ph. Eur., ≥99% (GC)
Packaging
100g
Price
$262
Updated
2024/03/01
Sigma-Aldrich
Product number
33420
Product name
1-Naphthol
Purity
puriss. p.a., reag. Ph. Eur., ≥99% (GC)
Packaging
250g
Price
$575
Updated
2024/03/01
More
Less

1-Naphthol Chemical Properties,Usage,Production

Description

1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C10H7OH. It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They are precursors to a variety of useful compounds. Naphthols (both 1 and 2 isomers) are used as biomarkers for livestock and humans exposed to polycyclic aromatic hydrocarbons.
α-naphtol, combined with epichlorhydrine and sodium hydroxide to form alpha-naphtyl glycidyl ether, caused sensitization in one of three workers in a chemical plant.

Chemical Properties

Pale grey to brown solid with an unpleasant phenol odour. Darkens in the presence of light. Evaporates with water vapour. Soluble in ethanol, ether, benzene, chloroform and alkali solutions, insoluble in water. Precipitates violet when exposed to ferric chloride. 1-Naphthol [90-15-3] a-naphthol, 1- naphthalenol, 1-hydroxynaphthalene, C10H8O, Mr 144.16, forms colorless prisms (from toluene) which darken on exposure to air or light. The compound is steam volatile and sublimable. 1-Naphthol is reduced by sodium in liquid ammonia to give 5,6,7,8-tetrahydro-1-naphthol and is oxidized by NaOCl – FeCl3 or I2–KI to give a violet color. It is chlorinated by phosphorus pentachloride at 150℃ to give 1-chloronaphthalene, by sulfuryl chloride to give 4- chloro-1-naphthol, or by Cl2–CH3COOH to give 2,4-dichloro-1-naphthol. Similarly bromine forms 2,4-dibromo-1-naphthol, and this reaction may be used quantitatively for titration. Nitration of 1-naphthol gives complex mixtures. The crude 2,4-dinitro derivative was used in the mid-1800s as an acid yellow dye comparable to picric acid. Sulfonation at 50℃ readily yields 1-naphthol-2,4-disulfonic acid. Nitrous acid gives mainly the 2-nitroso derivative, contaminated with the 4-nitroso isomer.

Uses

1-Naphthol is used as a precursor in the manufacturing of various azo dyes and pharmaceuticals such as nadolol. It is used as biomarkers. It is used in analytical chemistry as Molisch's reagent (1-naphthol dissolved in ethanol) for checking the presence of carbohydrates. It plays an essential role with sodium hypobromite to detect the presence of arginine in proteins, which is called as Sakaguchi test.

Preparation

2-Isopropylnaphthalene can be used to synthesize 1-naphthol by oxidation via the hydroperoxide (Hock synthesis).
Historically 1-naphthol was produced via caustic fusion of naphthalene-1-sulfonic acid, but this was superseded by the I.G. Farbenindustrie process involving hydrolysis of 1-naphthylamine with aqueous 22 % sulfuric acid at 200°C under pressure in a lead-lined autoclave. To obtain a purer product, Union Carbide developed a process based on catalytic oxidation of tetralin to 1-tetralol and 1-tetralone followed by dehydrogenation. The two-stage catalytic process is claimed to give an overall yield of 72% 1-naphthol, with an overall efficiency of 97%.

Application

1-Naphthol is a hydroxyl-aromatic compound. It has been used as a prooxidant to analyze its ability to induce hemolysis in a zebrafish G6PD (glucose-6-phosphate dehydrogenase) deficiency model.

Definition

ChEBI: 1-naphthol is a naphthol carrying a hydroxy group at position 1. It has a role as a genotoxin and a human xenobiotic metabolite.

Synthesis Reference(s)

Synthetic Communications, 21, p. 379, 1991 DOI: 10.1080/00397919108016759
Journal of the American Chemical Society, 107, p. 493, 1985 DOI: 10.1021/ja00288a037

General Description

1-Naphthol, a metabolite of carbaryl and naphthanlene. It is formed by spontaneous reaction from (1R, 2S)-Naphthalene epoxide followed to form 1, 4-Dihydroxynaphthalene.

Hazard

Toxic by ingestion and skin absorption.

Flammability and Explosibility

Not classified

Contact allergens

1-Naphthol can be used in dye manufacture and is classified as a hair dye. Combined with epichlorhydrin and NaOH to form alpha-naphthyl glycidyl ether, it caused sensitization in one of three workers in a chemical plant.

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by skin contact. An experimental teratogen. Experimental reproductive effects. A severe eye and skin irritant. Mutation data reported. Ingestion of large amounts can cause nephritis, vomiting, diarrhea, circulatory collapse, anemia, convulsions, and death. Can cause kidney irritation and injury to cornea and lens of the eye. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

To a 10 mL pressure vessel, aryl halide (1.00 mmol), copper (I) oxide (0.05 mol), ligand (0.05 mol), 3 M sodium hydroxide (2 mL), and organic solvent (2 mL) were added. The reaction mixture was irradiated at 160 °C for 10 min with strong stirring. The reaction mixture was allowed to cool to room temperature. The reaction mixture was filtered through a plug of celite in a fritted filter funnel and washed with ethyl acetate. The product was extracted using 30 mL of ethyl acetate for three times. The organic extract is washed three times with 10 mL water and two times with 10 mL of brine. The combined organic phases were dried over anhydrous MgSO4 and the solvent was removed under reduced pressure to afford 1-naphthol.

Purification Methods

Sublime 1-naphthol, then crystallise it from aqueous MeOH (charcoal), aqueous 25% or 50% EtOH, *C6H6, cyclohexane, heptane, CCl4 or H2O. Dry it over P2O5 in vacuo. The 4-nitrobenzoate has m 143o (from EtOH). [Shizuka et al. J Am Chem Soc 107 7816 1985, Beilstein 8 H 596, 6 IV 4208.]

1-Naphthol Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

View Lastest Price from 1-Naphthol manufacturers

Jinan Finer Chemical Co., Ltd
Product
1-Naphthol 90-15-3
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
2000mt/year
Release date
2023-10-11
Hebei Jingbo New Material Technology Co., Ltd
Product
1-Naphthol 90-15-3
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000000
Release date
2023-12-28
Hebei Yanxi Chemical Co., Ltd.
Product
1-Naphthol 90-15-3
Price
US $0.00/kg
Min. Order
1kg
Purity
96%;99.5%;99.9%
Supply Ability
20tons
Release date
2023-09-27

90-15-3, 1-NaphtholRelated Search:


  • 1-naphthalenol
  • 1-NAPHTHOL
  • 1-naphtol
  • α-Hydroxynaphthalene
  • α-Maphthol
  • 1-napthol(alpha-napthol)
  • 1-naphthol (alpha)
  • 1-Naphthol 97+ %
  • 2-NAPHTHOL 99.1%
  • ALPHA NAPHTHO
  • BETA NAPTHOL 98% MIN.
  • BETA NAPHTHAL
  • 1-napthol(alpha-napthol) industrial grade
  • 1-NAPHTHOL (ALPHA), FOR ANALYTICAL PURPO SES
  • 1-NAPHTHOL, 99+%
  • 1-NAPHTHOL SIGMAULTRA
  • 1-NAPHTHOL, REAGENTPLUS TM, >= 99%
  • 1-NAPHTHOL (ALPHA), FOR FLUORESCENCE
  • 1-NAPHTHOL R. G., REAG. PH. EUR.
  • 1-NAPHTHOL PESTANAL
  • 1-NAPHTHOL MM(CRM STANDARD)
  • 1-NAPHTHOL 99.5+% FOR ANALYTICAL PURPOSE
  • 1-Naphthol-(A-Naphthol)
  • 1-NaphtholGr
  • 1-NaphtholA.R.
  • 1-Naphthol, tech., 98%
  • à-naphthol
  • 1-HYDROXYNAPTHALENE
  • NAPHTHOL-1
  • 1-HYDROXYNAPHTHALENE
  • ALPHA-HYDROXYNAPHTHALENE
  • ALPHA-NAPHTHOL
  • ALPHA-NAPTHOL
  • a-Naphthol
  • AKOS BBS-00004307
  • Fourrine 99
  • furro er
  • C.I. 76605
  • durafur developer d
  • Oxidation base 33
  • α-Naphthol
  • alpha-naphtol
  • Basf Ursol ERN
  • basfursolern
  • C.I. Oxidation Base 33
  • c.i.oxidationbase33
  • cioxidationbase33
  • Fouramine ERN
  • fouramineern
  • Fourrine ERN
  • ALPHA NAPHTHOL ( HIGH GRADE )
  • ALPHA NAPHTHOL ( INDUSTRIAL GRADE )
  • á-Naphthol
  • 1-Naphthol, Purified
  • 1-Naphthol, Reagent
  • Duloxetine EP IMpurity D
  • AR,99.0%
  • 1-Naphthol 0.5