Welcome to LookChem.com Sign In|Join Free

CAS

  • or

90-15-3

Post Buying Request

90-15-3 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

90-15-3 Usage

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.

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(Hock synthesis).Historically 1-naphthol was produced via caustic fusion of naphthalene-1-sulfonic acid, but this was superseded by the I.G. Farbenindustrie process involving hydrolysis of 1-naphthylamine with aqueous 22 % sulfuric acid at 200°C under pressure in a lead-lined autoclave.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%.

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.

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.

Synthesis Reference(s)

Synthetic Communications, 21, p. 379, 1991 DOI: 10.1080/00397919108016759Journal 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

Notclassified

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.

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 90-15-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 0 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 90-15:
(4*9)+(3*0)+(2*1)+(1*5)=43
43 % 10 = 3
So 90-15-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H

90-15-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (N0864)  1-Naphthol [for Biochemical Research]  >98.0%(GC)

  • 90-15-3

  • 1g

  • 195.00CNY

  • Detail
  • TCI America

  • (N0864)  1-Naphthol [for Biochemical Research]  >98.0%(GC)

  • 90-15-3

  • 5g

  • 480.00CNY

  • Detail
  • Alfa Aesar

  • (A11862)  1-Naphthol, 99%   

  • 90-15-3

  • 100g

  • 213.0CNY

  • Detail
  • Alfa Aesar

  • (A11862)  1-Naphthol, 99%   

  • 90-15-3

  • 500g

  • 567.0CNY

  • Detail
  • Alfa Aesar

  • (A11862)  1-Naphthol, 99%   

  • 90-15-3

  • 2500g

  • 2257.0CNY

  • Detail
  • Sigma-Aldrich

  • (80025)  1-Naphthol  certified reference material, TraceCERT®

  • 90-15-3

  • 80025-100MG

  • 802.62CNY

  • Detail
  • Sigma-Aldrich

  • (N2780)  1-Naphthol  BioXtra, ≥99%

  • 90-15-3

  • N2780-10G

  • 639.99CNY

  • Detail
  • Sigma-Aldrich

  • (N2780)  1-Naphthol  BioXtra, ≥99%

  • 90-15-3

  • N2780-100G

  • 3,212.82CNY

  • Detail
  • Sigma-Aldrich

  • (33420)  1-Naphthol  puriss. p.a., Reag. Ph. Eur., ≥99% (GC)

  • 90-15-3

  • 33420-100G-R

  • 1,621.62CNY

  • Detail
  • Sigma-Aldrich

  • (33420)  1-Naphthol  puriss. p.a., Reag. Ph. Eur., ≥99% (GC)

  • 90-15-3

  • 33420-250G-R

  • 3,036.15CNY

  • Detail
  • Sigma-Aldrich

  • (N1000)  1-Naphthol  ReagentPlus®, ≥99%

  • 90-15-3

  • N1000-10G

  • 372.06CNY

  • Detail
  • Sigma-Aldrich

  • (N1000)  1-Naphthol  ReagentPlus®, ≥99%

  • 90-15-3

  • N1000-100G

  • 1,618.11CNY

  • Detail

90-15-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-naphthol

1.2 Other means of identification

Product number -
Other names 1-hydroxynaphthalene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:90-15-3 SDS

90-15-3Synthetic route

1-naphthyl acetate
830-81-9

1-naphthyl acetate

α-naphthol
90-15-3

α-naphthol

Conditions
ConditionsYield
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 12h;100%
With lipase of Pseudomonas sp; water In various solvent(s) at 25℃; for 1.5h; Hydrolysis; deacetylation;100%
With sodium tetrahydroborate; cobalt(II) chloride In ethanol at 0 - 25℃; for 10h;98%
1-naphthyl tetrahydro-2H-pyran-2-yl ether
80116-05-8

1-naphthyl tetrahydro-2H-pyran-2-yl ether

α-naphthol
90-15-3

α-naphthol

Conditions
ConditionsYield
With acid-washed bentonite In acetone at 40 - 50℃; for 0.166667h;100%
With montmorillonite K-10 In methanol at 40 - 50℃; for 0.6h;96%
With methanol at 20℃; for 2.16667h;92%
trimethyl(1-naphthaleneoxy)silane
6202-48-8

trimethyl(1-naphthaleneoxy)silane

α-naphthol
90-15-3

α-naphthol

Conditions
ConditionsYield
montmorillonite K-10 for 0.0833333h; Solid phase reaction; desilylation; microwave irradiation;100%
With bismuth(lll) trifluoromethanesulfonate In methanol at 20℃; for 0.0333333h;98%
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;97%
1,4-epoxy-1,4-dihydronaphthalene
573-57-9

1,4-epoxy-1,4-dihydronaphthalene

α-naphthol
90-15-3

α-naphthol

Conditions
ConditionsYield
With dichlorotricarbonylruthenium(II) dimer In 1,2-dichloro-ethane at 60℃; for 18h; Inert atmosphere; regioselective reaction;100%
at 80℃; for 12h; Temperature; Green chemistry;99%
With methanol; dichlorotricarbonylruthenium(II) dimer at 65℃; for 1h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere;45%
Multi-step reaction with 2 steps
1: chloro(1,5-cyclooctadiene)rhodium(I) dimer
2: perchloric acid / water / 25 °C
View Scheme
Stage #1: 1,4-epoxy-1,4-dihydronaphthalene With (Rp)-pseudo-o-bis(di(3,5-dimethylphenyl)phosphino)[2.2]paracyclophane; bis(1,5-cyclooctadiene)diiridium(I) dichloride In tetrahydrofuran for 0.333333h; Inert atmosphere;
Stage #2: With 1-Phenylprop-1-yne In tetrahydrofuran at 90℃; Inert atmosphere;
1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

α-naphthol
90-15-3

α-naphthol

Conditions
ConditionsYield
With water; 3-chloro-benzenecarboperoxoic acid In ethanol at 20℃; for 6h;100%
With dihydrogen peroxide at 30℃; for 5h; Green chemistry;98%
With water; dihydrogen peroxide at 20℃; for 0.166667h; Green chemistry;97%
3,4-dihydronaphthalene-1(2H)-one
529-34-0

3,4-dihydronaphthalene-1(2H)-one

α-naphthol
90-15-3

α-naphthol

Conditions
ConditionsYield
With (difluoroboryl)dimethylglyoximatocobalt(II) bis(acetonitrile); boron trifluoride diethyl etherate; 3-cyano-1-methylquinolinium perchlorate In acetonitrile at 20℃; for 0.5h; Irradiation; Inert atmosphere; Flow reactor;99%
With Oxone; ammonium bromide In dichloromethane90%
With 5 mol% Pd/C; hydrogen; potassium carbonate In N,N-dimethyl acetamide at 150℃; under 608.041 Torr; for 10h;81%

90-15-3Relevant articles and documents

Ziegler et al.

, p. 208,211 (1965)

Dediazoniation of 1-naphthalenediazonium tetrafluoroborate in aqueous acid and in micellar solutions

Bravo-Diaz, Carlos,Pastoriza-Gallego, Maria Jose,Losada-Barreiro, Sonia,Sanchez-Paz, Veronica,Fernandez-Alonso, Alejandra

, p. 301 - 309 (2008)

We have measured the rates and product yields of dediazoniation of 1-naphthalenediazonium (1ND) tetrafluoroborate in the presence and absence of sodium dodecyl sulfate (SDS) micellar aggregates by employing a combination of UV-vis spectroscopy and high-performance liquid chromatography (HPLC) measurements. Kinetic data were obtained by a derivatization procedure with product yields were determined by HPLC. HPLC chromatograms show that in aqueous acid and in micellar solutions only one dediazoniation product is formed in significant quantities, 1-naphthol (NOH), and the observed rate constants (kobs) are tne same when IND loss is monitored spectrometrically and when NOH formation is monitored by HPLC. Activation parameters were obtained both in the presence and absence of SDS micellar aggregates. In both the systems, the enthalpies of activation are high and the entropies of activation are positive. The enthalpy of activation in the absence of SDS is very similar to that in the presence of SDS micelles, but the entropy of activation is lower by a factor of 4. As a consequence, SDS micelles speed up the thermal decomposition of 1 ND and increase kobs by a factor of 1.5 when [SDS] = 0.02 M. In contrast, results obtained in the presence of complexing systems such as crown ethers and polyethers show significant stabilization of the parent arenediazonium ions. Kinetic and HPLC data are consistent with the heterolytic DN + AN mechanism that involves the rate-determining fragmentation of the arenediazonium ion into a very reactive phenyl cation that reacts competitively with available nucleophiles.

Ultrasensitive self-enhanced electrochemiluminescence sensor based on novel PAN?Ru?PEI?Nafion nanofiber mat

Li, Libo,Liu, Xiaohong,You, Tianyan,Zhou, Limin

, p. 3590 - 3597 (2020)

In the present work, a novel self-enhanced electrochemiluminescence (ECL) composite was for the first time prepared by simply electrospinning a mixture of polyacrylonitrile (PAN), Ru(bpy)32+, poly(ethylenimine) (PEI) and Nafion, and defined as PAN?Ru?PEI?Nafion nanofiber mat (PAN?Ru?PEI?Nafionnfm). Herein, Ru(bpy)32+was applied as an ECL reagent, and PEI was selected as a co-reactant due to the abundant tertiary amine groups in its backbone. In order to further improve the ECL efficiency of the Ru(bpy)32+-PEI system, we innovatively loaded Ru(bpy)32+and PEI into PAN nanofibers simultaneously by a one-step electrospinning technique. As a result, the electronic transmission distance between them was sharply shortened. Meanwhile, with the help of electrostatic interaction between positively charged Ru(bpy)32+or PEI and negatively charged Nafion, exfoliation of Ru(bpy)32+and PEI from the PAN nanofiber mat was effectively avoided. As expected, the luminous nanofibers exhibited excellent ECL performance including high efficiency and good stability. On this basis, we fabricated a new self-enhanced ECL sensor with excellent analysis performance. Using a-naphthol as an analytical probe, the sensor showed a wide linear range from 1.0 × 10-12to 1.0 × 10-7M with a low detection limit of 1.0 × 10-12M. When it was applied to detect a-naphthol from carbaryl hydrolysis, the results were well consistent with those obtained from the high efficiency liquid chromatography-diode array detector (HPLC-DAD) method, indicating the potential application of the ECL sensor in real sample assays.

Menon

, p. 1061 (1935)

Rabbit serum albumin hydrolyzes the carbamate carbaryl

Sogorb, Miguel A.,Carrera, Victoria,Benabent, Monica,Vilanova, Eugenio

, p. 520 - 526 (2002)

One of the main detoxification processes of the carbamate insecticides is the hydrolysis of the carbamic ester bond. Carboxylesterases seem to play important roles in the metabolization of carbamates. This study performs a biochemical characterization of the capabilities of rabbit serum albumin (RSA) to hydrolyze the carbamate carbaryl. Rabbit serum albumin was able to hydrolyze carbaryl with a Kcat of 7.1 × 10-5 s-1. The Km for this hydrolysis reaction was 240 μM. Human, chicken, and bovine serum albumins were also able to hydrolyze carbaryl. The divalent cation Cu2+ at 1 mM concentration inhibited around 50% of the hydrolysis of carbaryl by RSA. Other mono- and divalent cations at 1 mM concentration and 5 mM EDTA exerted no significant effects on the hydrolysis of carbaryl by RSA. The inhibition of the carbaryl hydrolysis by sulfydril blocking agents suggests that a cysteine residue plays an important role in the active center of the catalytic activity. Both caprylic and palmitic acids were noncompetitive inhibitors of the carbaryl hydrolysis by RSA. The carboxyl ester p-nitrophenyl butyrate is a substrate of RSA and competitively inhibited the hydrolysis of carbaryl by this protein, suggesting that the hydrolysis of carbaryl and the hydrolysis of carboxyl esters occur in the same catalytic site and through a similar mechanism. This mechanism might be based on the carbamylation of a tyrosine residue of the RSA. Serum albumin is a protein universally present in nontarget species of insecticides; therefore, the capability of this protein to hydrolyze other carbamates must be studied because it might have important toxicological and ecotoxicological implications.

Photocatalytic conversion of naphthalene to α-naphthol using nanometer-sized TiO2

Shi, Huixian,Zhang, Tianyong,Wang, Hongliang,Wang, Xiao,He, Meng

, p. 46 - 50 (2011)

The effects of various parameters (co-solvents, electron acceptors, and surface modification) on the direct synthesis of α-naphthol from naphthalene using photocatalytic processes were investigated. The OH radicals generated on UV-illuminated TiO2 photocatalysts led to the direct hydroxylation of naphthalene to α-naphthol. The addition of Fe 3+, Fe2+, Fe3+ + H2O2, and Fe2+ + H2O2 greatly increases the conversion of naphthalene and the yield of α-naphthol in TiO2 suspensions. The addition of Fe3+ + H2O2 to a TiO2 suspension increased the yield to 22.2. Surface modified-TiO2 had a significant influence on the hydroxylation reaction. La-Eu/TiO2, La-Y/TiO2, H3PW 12O40/TiO2, H3PMo12O 40/TiO2, Fe/TiO2, Ag/TiO2, Cu/TiO2, and N/TiO2 enhanced the conversion and yield more than TiO2. Fe/TiO2 has the highest photocatalytic efficiency among these species.

Determination of the hydrolysis kinetics of α-naphthyl acetate in micellar systems and the effect of HPMC (catalyst present)

Werawatganone, Pornpen,Wurster, Dale Eric

, p. 448 - 458 (2007)

The change in the hexadecyltrimethylammonium bromide (CTAB) critical aggregation concentration (CAC) was studied in the presence of various concentrations and grades of hydroxypropylmethyl cellulose (HPMC) using surface tension measurement (duNouey ring and Wilhelmy plate) and oil red O solubilization. According to the surface tension methods, the CAC was higher than the CTAB critical micelle concentration (CMC). CAC and CMC were not different when the solubilization method was used. Micellar solutions of CTAB have been found to accelerate the hydrolysis of α-naphthyl acetate (α-NA) by o-iodosobenzoic acid (IBA), a strong nucleophile. Pseudo-first-order kinetics were utilized for rate constant determination. The observed rate constants for the degradation of α-NA in the presence of varying CTAB concentrations with and without HPMC were analyzed according to the pseudophase model. The micellar rate constants and the micellar binding constants for the substrates were obtained. The presence of HPMC retarded the reaction rate, and the rate constant decreased as the polymer concentration increased. However, there was no obvious difference in the observed rate constants among the different grades of HPMC (Methocel E5, Methocel E15, Methocel E50). The decrease in the rate constant was likely due to the polymer-micelle interaction interfering with substrate binding to the CTAB micelles.

Imidazolium-urea low transition temperature mixtures for the UHP-promoted oxidation of boron compounds

Martos, Mario,Pastor, Isidro M.

, (2022/01/03)

Different carboxy-functionalized imidazolium salts have been considered as components of low transition temperature mixtures (LTTMs) in combination with urea. Among them, a novel LTTM based on 1-(methoxycarbonyl)methyl-3-methylimidazolium chloride and urea has been prepared and characterized by differential scanning calorimetry throughout its entire composition range. This LTTM has been employed for the oxidation of boron reagents using urea-hydrogen peroxide adduct (UHP) as the oxidizer, thus avoiding the use of aqueous H2O2, which is dangerous to handle. This metal-free protocol affords the corresponding alcohols in good to quantitative yields in up to 5 mmol scale without the need of further purification. The broad composition range of the LTTM allows for the reaction to be carried out up to three consecutive times with a single imidazolium salt loading offering remarkable sustainability with an E-factor of 7.9, which can be reduced to 3.2 by the threefold reuse of the system.

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction

-

Paragraph 0152-0158, (2021/05/29)

The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.

Photocatalytic Reductive C-O Bond Cleavage of Alkyl Aryl Ethers by Using Carbazole Catalysts with Cesium Carbonate

Yabuta, Tatsushi,Hayashi, Masahiko,Matsubara, Ryosuke

, p. 2545 - 2555 (2021/02/01)

Methods to activate the relatively stable ether C-O bonds and convert them to other functional groups are desirable. One-electron reduction of ethers is a potentially promising route to cleave the C-O bond. However, owing to the highly negative redox potential of alkyl aryl ethers (Ered -2.6 V vs SCE), this mode of ether C-O bond activation is challenging. Herein, we report the visible-light-induced photocatalytic cleavage of the alkyl aryl ether C-O bond using a carbazole-based organic photocatalyst (PC). Both benzylic and non-benzylic aryl ethers underwent C-O bond cleavage to form the corresponding phenol products. Addition of Cs2CO3 was beneficial, especially in reactions using a N-H carbazole PC. The reaction was proposed to occur via single-electron transfer (SET) from the excited-state carbazole to the substrate ether. Interaction of the N-H carbazole PC with Cs2CO3 via hydrogen bonding exists, which enables a deprotonation-assisted electron-transfer mechanism to operate. In addition, the Lewis acidic Cs cation interacts with the substrate alkyl aryl ether to activate it as an electron acceptor. The high reducing ability of the carbazole combined with the beneficial effects of Cs2CO3 made this otherwise formidable SET event possible.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 90-15-3