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91-20-3

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91-20-3 Usage

Description

Naphthalene is a commercially important aromatic hydrocarbon that occurs as transparent prismatic plates or as white scales, powder, balls, or cakes with a characteristic mothball or strong coal tar and aromatic odour. It is sparingly soluble in water but soluble in methanol/ethanol and very soluble in ether. Naphthalene occurs in coal tar in large quantities and is easily isolated from this source in pure condition. It volatilises and sublimes at room temperature above the melting point.

Uses

Used in Chemical Industry:
Naphthalene is used as a hydrocarbon raw material for the production of phthalic anhydride, carbamate insecticides, surface active agents, and resins. It is also used as a dye intermediate, synthetic tanning agent, and in miscellaneous organic chemicals.
Used in Plastics and Resins Production:
Naphthalene is used as an intermediate in the production of phthalate plasticizers, other plastics, and resins. It is catalytically oxidized to phthalic anhydride, which is used to produce plastics, phthalate plasticizers, insecticides, pharmaceuticals, and resins.
Used in Insecticides and Pest Control:
Naphthalene is used in the production of carbamate insecticides such as carbaryl, a wide-spectrum, general-purpose insecticide. It is also used in mothballs and other moth repellants, as well as solid block deodorizers for toilets and diaper pails.
Used in Dyes and Tanning Industry:
Naphthalene is used in the manufacture of phthalic and anthranilic acids to make indigo, indanthrene, and triphenyl methane dyes. It is also used as a synthetic tanning agent.
Used in Miscellaneous Applications:
Naphthalene is used in dusting powders, lavatory deodorant discs, wood preservatives, fungicides, and as an insecticide. It has been used as an intestinal antiseptic and vermicide and in the treatment of pediculosis and scabies.
Used in Research and Development:
Naphthalene has been used in liquid-phase exfoliation of graphite in organic solvents for the production of graphene sheets. It has also been used in the preparation of carbon-coated Si70Sn30 nanoparticles, as a fluorescent probe to study the aggregation behavior of sodium cholate, and to investigate the influence of added short chain linear and branched alcohols on the binding of 1:1 complex of naphthalene and β-cyclodextrin.

Health Hazard

Most of the data available on the toxic effects of naphthalene have been derived from animal studies conducted either in vivo or with in vitro preparations. Rats and mice breathing naphthalene vapors daily for a lifetime had irritated noses and nose tumors and irritated lungs. Some female mice had lung tumors. Some animals got cloudy eyes after ingesting it. It is not clear if naphthalene causes reproductive problems in animals. Although there is no direct data showing that naphthalene can cause cancer in people, naphthalene exposure can lead to cancer in animals. Exposure to large amounts of naphthalene may damage or destroy red blood cells, a condition called hemolytic anemia. Symptoms of hemolytic anemia are feeling very tired or restless, lack of appetite, and pale skin. Exposure to large amounts of naphthalene may also cause upset stomach, diarrhea, blood in the urine,and yellow-colored skin. Very young children and unborn children are at higher risk if they are exposed to naphthalene, especially if they ingest the chemical. Some infants have become ill when they were close to clothing or blankets stored in naphthalene mothballs.

Health Hazard

Inhalation of naphthalene vapor may causeirritation of the eyes, skin, and respiratorytract, and injury to the cornea. Other symptoms are headache, nausea, confusion, andexcitability. The routes of exposure of thiscompound into the body are inhalation, ingestion, and absorption through the skin; andthe organs that may be affected are the eyes,liver, kidney, blood, skin, and central nervoussystem.The most severe toxic effects from naphthalene, however, may come from oral intakeof large doses of this compound. In animals, as well as in humans, ingestion of largeamounts may cause acute hemolytic anemiaand hemoglobinuria attributed to its metabolites, 1- and 2-naphthol and naphthoquinones.Infants are more sensitive than adults becauseof their lower capacity for methemoglobinreduction. Other symptoms from ingestion ofnaphthalene are gastrointestinal pain and kidney damage. The LD50 values reported inthe literature show variation among differentspecies. In mice, an oral LD50 value may beon the order of 600 mg/kg. Symptoms of respiratory depression and ataxia were noted.Chronic exposure to naphthalene vapormay affect the eyes, causing opacities of thelens and optical neuritis. The acute effectsfrom inhalation of its vapors at high concentrations are nausea and vomiting.Inhalation studies have shown positivetumorigenic response in mice. Studies conducted under National Toxicology Program(NTP) show clear evidence of carcinogenicityin rats resulting from inhalation of naphthalene vapors (NTP 2000). Increased incidencesof respiratory epithelial adenoma and olfactory epithelial neuroblastoma in the nose wereobserved in both the sexes of rats. On thebasis of these findings IARC has reevaluatednaphthalene and reclassified it under Group2B carcinogen, as possibly carcinogenic tohumans (IARC 2002)..

Toxicity

Naphthalene is a white solid substance with a strong smell. Poisoning from naphthalene destroys or changes red blood cells so they cannot carry oxygen. This can cause organ damage. In humans, naphthalene is broken down to alpha-naphthol, which is linked to the development of hemolytic anemia. Kidney and liver damage may also occur. Alpha-naphthol and other metabolites are excreted in urine. In animals, naphthalene breaks down into other compounds including alpha-naphthol, which may affect the lungs and eyes. Naphthalene was found in the milk of exposed cows, but the residues disappeared quickly after the cows were no longer exposed. Nearly all the naphthalene was broken down into other compounds and excreted in their urine.

History

In 1819, naphthalene was obtained as white crystals during the pyrolysis of coal tar by John Kidd (1775–1851), a British physician and chemist, and Alexander Garden (1757–1829), an American living in Britain. Kidd described the properties of the white crystals he obtained from coal tar and proposed the named naphthaline for the substance; naphthaline was derived from naphtha, a general term for a volatile, fl ammable, hydrocarbon liquid. Michael Faraday (1791–1867) determined the correct empirical formula for naphthalene in 1825, and Richard August Carl Emil Erlenmeyer (1825–1909) proposed the fused benzene ring structure in 1866.

Production Methods

Naphthalene is produced from coal tar or petroleum. It is made from petroleum by dealkylationof methylnaphthalenes in the presence of hydrogen at high temperature and pressure.Petroleum was a major source of naphthalene until the 1980s, but now most naphthaleneis produced from coal tar. The pyrolysis of bituminous coal produces coke and coke ovengases. Naphthalene is condensed by cooling the coke gas and then separated from the gas.

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 3686, 1974 DOI: 10.1021/ja00818a072The Journal of Organic Chemistry, 54, p. 4474, 1989 DOI: 10.1021/jo00279a046Tetrahedron Letters, 27, p. 5541, 1986 DOI: 10.1016/S0040-4039(00)85262-4

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as Naphthalene, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction. Naphthalene, camphor, glycerol, or turpentine will react violently with chromic anhydride [Haz. Chem. Data 1967. p 68]. Friedel-Crafts acylation of Naphthalene using benzoyl chloride, catalyzed by AlCl3, must be conducted above the melting point of the mixture, or the reaction may be violent [Clar, E. et al., Tetrahedron, 1974, 30, 3296].

Hazard

Toxic by inhalation. Upper respiratory tract irritant, cataracts and hemolytic anemia. Possible carcinogen.

Fire Hazard

Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished.

Flammability and Explosibility

Flammable

Safety Profile

Human poison by ingestion. Experimental poison by ingestion, intravenous, and intraperitoneal routes. Moderately toxic by subcutaneous route. An experimental teratogen. Experimental reproductive effects. An eye and skin irritant. Can cause nausea, headache, daphoresis, hematuria, fever, anemia, liver damage, vomiting, convulsions, and coma. Poisoning may occur by ingestion of large doses, inhalation, or skin absorption. Questionable carcinogen with experimental tumorigenic data. Flammable when exposed to heat or flame; reacts with oxidizing materials. Explosive reaction with dinitrogen pentaoxide. Reacts violently with CrOs, aluminum chloride + benzoyl chloride. Fires in the benzene scrubbers of coke oven gas plants have been attributed to oxidation of naphthalene. Explosive in the form of vapor or dust when exposed to heat or flame. To fight fire, use water, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Naphthalene is used as a chemical intermediate or feedstock for synthesis of phthalic, anthranilic, hydroxyl (naphthols), amino (naphthylamines), and sulfonic compounds; which are used in the manufacture of various dyes and in the preparation of phthalic anhydride, 1-naphthyl-N-methyl carbonate; and β-naphthol. Naphthalene is also used in the manufacture of hydronaphthalenes, synthetic resins; lampblack, smokeless powder; and celluloid. Naphthalene has been used as a moth repellent. Approximately 100 million people worldwide have G6PD deficiency which would make them more susceptible to hemolytic anemia on exposure to naphthalene. At present, more than 80 variants of this enzyme deficiency have been identified. The incidence of this deficiency is 0.1% in American and European Caucasians, but can range as high as 20% in American blacks and greater than 50% in certain Jewish groups. Newborn infants have a similar sensitivity to the hemolytic effects of naphthalene, even without G6PD deficiency.

Carcinogenicity

Naphthalene is reasonably anticipated to be a human carcinogenbased on sufficient evidence from studies in experimental animals.

Shipping

UN1334 Naphthalene, crude or Naphthalene, refined, Hazard Class: 4.1; Labels: 4.1-Flammable solid. UN2304 (molten) Hazard Class: 4.1; Labels: 4.1-Flammable solid.

Purification Methods

Crystallise naphthalene once or more times from the following solvents: EtOH, MeOH, CCl4, *C6H6, glacial acetic acid, acetone or diethyl ether, followed by drying at 60o in an Abderhalden drying apparatus. It has also been purified by vacuum sublimation and by fractional crystallisation from its melt. Other purification procedures include refluxing in EtOH over Raney Ni and chromatography of a CCl4 solution on alumina with *benzene as eluting solvent. Baly and Tuck [J Chem Soc 1902 1908] purified naphthalene for spectroscopy by heating with conc H2SO4 and MnO2, followed by steam distillation (repeating the process), and formation of the picrate which, after recrystallisation (m 150o) is decomposed with base and the naphthalene is steam distilled. It is then crystallised from dilute EtOH. It can be dried over P2O5 under vacuum (take care not to make it sublime). Also purify it by sublimation and subsequent crystallisation from cyclohexane. Alternatively, it has been washed at 85o with 10% NaOH to remove phenols, with 50% NaOH to remove nitriles, with 10% H2SO4 to remove organic bases, and with 0.8g AlCl3 to remove thianaphthalenes and various alkyl derivatives. Then it is treated with 20% H2SO4, 15% Na2CO3 and finally distilled. [Gorman et al. J Am Chem Soc 107 4404 1985.] Zone refining purified naphthalene from anthracene, 2,4-dinitrophenylhydrazine, methyl violet, benzoic acid, methyl red, chrysene, pentacene and indoline. [Beilstein 5 IV 1640.]

Toxicity evaluation

Systemic absorption of naphthalene vapor may result in cataracts. The biochemical basis for naphthalene cataract has been investigated. Naphthalene is metabolized in the liver to 1,2-dihydro-1,2-dihydroxynaphthalene. Lenticular catechol reductase biotransforms 1,2-dihydro-1,2-dihydroxynaphthalene to 1,2-dihydroxynaphthalene, which, in turn, is auto-oxidized in air at neutral pH to 1,2-naphthoquinone and hydrogen peroxide. Ascorbic acid reverses the latter reaction and forms dehydroascorbic acid, which diffuses out of the lens very slowly. Dehydroascorbic acid has been shown to accumulate in the lens of rabbits that were fed naphthalene and lens incubated in vitro with 1,2-dihydro- 1,2-dihydroxynaphthalene. The sequence of reactions involves the reduction of ascorbic acid by 1,2-naphthoquinone in the aqueous humor to dehydroascorbic acid, which rapidly penetrates the lens and is reduced by glutathione. Oxidized glutathione and 1,2-naphthoquinone may compete for enzyme glutathione reductase, which normally maintains high reticular levels of reduced glutathione. A reduction in the concentration of these coupled with the removal of oxygen from the aqueous humor due to the autooxidation of 1,2-dihydroxynaphthalene may make the lens sensitive to naphthalene toxicity.

Incompatibilities

Dust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Violent reactions with chromium(III) oxide, dinitrogen pentoxide; chromic anhydride.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

Check Digit Verification of cas no

The CAS Registry Mumber 91-20-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 1 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 91-20:
(4*9)+(3*1)+(2*2)+(1*0)=43
43 % 10 = 3
So 91-20-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H

91-20-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A13188)  Naphthalene, 99+%   

  • 91-20-3

  • 250g

  • 258.0CNY

  • Detail
  • Alfa Aesar

  • (A13188)  Naphthalene, 99+%   

  • 91-20-3

  • 1000g

  • 442.0CNY

  • Detail
  • Alfa Aesar

  • (A13188)  Naphthalene, 99+%   

  • 91-20-3

  • 5000g

  • 1676.0CNY

  • Detail
  • Alfa Aesar

  • (33347)  Naphthalene, 99.6%   

  • 91-20-3

  • 50g

  • 276.0CNY

  • Detail
  • Alfa Aesar

  • (33347)  Naphthalene, 99.6%   

  • 91-20-3

  • 500g

  • 471.0CNY

  • Detail
  • Alfa Aesar

  • (33347)  Naphthalene, 99.6%   

  • 91-20-3

  • 2kg

  • 1758.0CNY

  • Detail
  • Supelco

  • (40053)  Naphthalenesolution  certified reference material, 5000 μg/mL in methanol

  • 91-20-3

  • 000000000000040053

  • 545.22CNY

  • Detail
  • Sigma-Aldrich

  • (91489)  Naphthalene  certified reference material, TraceCERT®

  • 91-20-3

  • 91489-100MG

  • 1,075.23CNY

  • Detail
  • Supelco

  • (CRM48641)  Naphthalenesolution  certified reference material, 200 μg/mL in methanol

  • 91-20-3

  • CRM48641

  • 259.74CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1275)  Naphthalene  pharmaceutical secondary standard; traceable to USP

  • 91-20-3

  • PHR1275-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (84679)  Naphthalene  analytical standard

  • 91-20-3

  • 84679-250MG

  • 146.25CNY

  • Detail
  • Sigma-Aldrich

  • (84679)  Naphthalene  analytical standard

  • 91-20-3

  • 84679-1G

  • 476.19CNY

  • Detail

91-20-3SDS

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 naphthalene

1.2 Other means of identification

Product number -
Other names Naphthalene, , scintillation grade

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. The primary use for naphthalene is in the production of phthalic anhydride. However, o-xylene is replacing naphthalene as the preferred raw material for phthalic anhydride production. Other uses of naphthalene include carbamate insecticides, surface active agents and resins, as a dye intermediate, as a synthetic tanning agent, as a moth repellent, and in miscellaneous organic chemicals.
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:91-20-3 SDS

91-20-3Synthetic route

tetralin
119-64-2

tetralin

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With triisobutylaluminum; Co acetylacetonate In neat (no solvent) at 150 - 200℃; Product distribution; other solvent, catalyst and reagent; turnover time and inhibition of reaction and catalyst;100%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 1.33333h; Reflux;62%
With phenyl isocyanate; palladium on activated charcoal at 220℃; for 6h;57%
5-(2-Naphthyloxy)-1-phenyl-1H-tetrazole
17743-32-7

5-(2-Naphthyloxy)-1-phenyl-1H-tetrazole

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With ethanol; water; tetrabutylammonium hypophosphite; benzene; palladium on activated charcoal for 3h; Product distribution; hydrogenation in a biphasic solvent system, other H-donor, other time, different amounts of substrate or catalyst, addition of 18-crown-6-ether;100%
3,5-dimethyl-1-phenyl-1H-pyrazole
1131-16-4

3,5-dimethyl-1-phenyl-1H-pyrazole

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
at 920℃; under 0.7 Torr; for 1.66667E-05h; Mechanism; flash vacuum thermolysis;100%
1-Methoxy-1.2-dihydronaphthalin
75896-23-0

1-Methoxy-1.2-dihydronaphthalin

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With silica gel100%
2,3,6,7-tetrakis(trimethylsilyl)naphthalene
62131-91-3

2,3,6,7-tetrakis(trimethylsilyl)naphthalene

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In tetrachloromethane for 12h; Ambient temperature;100%
3-benzotellurepine
135447-30-2

3-benzotellurepine

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
for 72h; Product distribution; Ambient temperature; other tellurepines;100%
In (2)H8-toluene at 40.3℃; Kinetics; Further Variations:; Temperatures;100%
1-methoxy-1,4-dihydronaphthalene
75896-22-9

1-methoxy-1,4-dihydronaphthalene

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With silica gel100%
1-Chloronaphthalene
90-13-1

1-Chloronaphthalene

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With water; sodium iodide; nickel dichloride; zinc; sonication In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 8h; Product distribution;100%
With water; sodium iodide; nickel dichloride; zinc; sonication In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 8h;100%
With ammonium formate In water at 20℃; for 6h;99%
triethylsilane
617-86-7

triethylsilane

(2RS,3RS,4RS,5RS,6RS,7RS)-3,6-dimesityl-3,6-bis<2,4,6-trisphenyl>-3,6-disilatetracyclo<6.4.02,4.05,7>dodeca-1(8),9,11-triene

(2RS,3RS,4RS,5RS,6RS,7RS)-3,6-dimesityl-3,6-bis<2,4,6-trisphenyl>-3,6-disilatetracyclo<6.4.02,4.05,7>dodeca-1(8),9,11-triene

A

naphthalene
91-20-3

naphthalene

B

2-<2,4,6-trisphenyl>-1,1,1-triethyl-2-mesityldisilane

2-<2,4,6-trisphenyl>-1,1,1-triethyl-2-mesityldisilane

Conditions
ConditionsYield
In (2)H8-toluene at 120℃; for 30h;A n/a
B 100%
Benzo[d]thiepine
264-14-2

Benzo[d]thiepine

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
In (2)H8-toluene at 23℃; Kinetics; Further Variations:; Temperatures;100%
7-Selena-benzocycloheptene

7-Selena-benzocycloheptene

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
In (2)H8-toluene at 22.8℃; Kinetics; Further Variations:; Temperatures;100%
7-Phenyl-7H-7-arsa-benzocycloheptene

7-Phenyl-7H-7-arsa-benzocycloheptene

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
In (2)H8-toluene at 22.3℃; Kinetics; Further Variations:; Temperatures;100%
oxirane
75-21-8

oxirane

(naphthalene)Yb(THF)3

(naphthalene)Yb(THF)3

A

naphthalene
91-20-3

naphthalene

B

Butane-1,4-diol
110-63-4

Butane-1,4-diol

C

ytterbium hydroxide

ytterbium hydroxide

Conditions
ConditionsYield
With hydrogen cation In tetrahydrofuran shaken for 10 min at room temp.; centrifuged, decanted, soln. contains naphthalene, pptn. hydrolysed in THF: butanediol detd. by GLC in the organic layer and a pptn. (Yb(OH)3);A 83%
B 100%
C 75%
1,2,3,4-tetrahydronaphthalene-1,4-diacetate
79909-37-8

1,2,3,4-tetrahydronaphthalene-1,4-diacetate

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
at 80 - 180℃; under 40 Torr;99.8%
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 6h; ultrasonic acceleration of reduction;99%
With 2,2'-azobis(isobutyronitrile); tert-butyl(2,6-dimethoxy-1-methylcyclohexa-2,5-dien-1-yl)dimethylsilane In hexane for 18h; Heating;99%
With 2,2'-azobis(isobutyronitrile); tert-butyl(2,6-dimethoxy-1-methylcyclohexa-2,5-dien-1-yl)dimethylsilane In hexane for 18h; Heating;99%
1-Fluoronaphthalene
321-38-0

1-Fluoronaphthalene

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With palladium 10% on activated carbon In isopropyl alcohol at 100℃; for 12h; Inert atmosphere;99%
With C32H46N2Ru; sodium carbonate; isopropyl alcohol at 70℃; for 96h; Inert atmosphere; Schlenk technique; Glovebox;96%
With s-butylmagnesium chloride; bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 50℃; for 12h; Product distribution / selectivity;88%
1-Iodonaphthalene
90-14-2

1-Iodonaphthalene

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 6h; ultrasonic acceleration of reduction;99%
With formaldehyd; palladium diacetate; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h; Kinetics; Reagent/catalyst;99%
With tri-n-butyl-tin hydride In acetonitrile at 20℃; for 24h; Irradiation; Inert atmosphere;97%
1-Methoxynaphthalene
2216-69-5

1-Methoxynaphthalene

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); (dimethoxy)methylsilane; tricyclohexylphosphine In toluene at 80℃; for 12h; Inert atmosphere;99%
With bis(1,5-cyclooctadiene)nickel(0); 1,1,3,3-Tetramethyldisiloxane; tricyclohexylphosphine In toluene at 110℃; for 14h; Inert atmosphere;77%
Multi-step reaction with 2 steps
1: NaBH4,m-dicyanobenzene / acetonitrile; H2O / 7 h / Irradiation
2: 100 percent / silica gel
View Scheme
tri(naphthalen-1-yl)bismuth
33397-22-7

tri(naphthalen-1-yl)bismuth

A

naphthalene
91-20-3

naphthalene

B

1-benzoylnaphthalene
642-29-5

1-benzoylnaphthalene

C

bismuth(III) chloride
7787-60-2

bismuth(III) chloride

Conditions
ConditionsYield
With aluminium trichloride; benzoic acid In chloroform 5 h reflux, molar ratio Bi(1-C10H7)3:AlCl3:C6H5COOH = 1:1:1;A 34%
B 9.3%
C 99%
With iron(III) chloride; benzoic acid In chloroform 5 h reflux, molar ratio Bi(1-C10H7)3:FeCl3:C6H5COOH = 1:1:1;A 44%
B 10.2%
C 96%
2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With triethylsilane; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine In toluene at 110℃; for 14h; Reagent/catalyst; Concentration; Solvent;99%
With isopropylmagnesium bromide; nickel diacetate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In tetrahydrofuran at 100℃; for 18h; Inert atmosphere; Sealed tube;70%
With bis(1,5-cyclooctadiene)nickel (0); sodium formate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride; sodium t-butanolate In toluene at 140℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique;63%
tri(naphthalen-1-yl)bismuth
33397-22-7

tri(naphthalen-1-yl)bismuth

A

naphthalene
91-20-3

naphthalene

B

bismuth(III) chloride
7787-60-2

bismuth(III) chloride

Conditions
ConditionsYield
With benzoic acid In chloroform molar ratio Bi(1-C10H7)3:C6H5COOH = 1:1;A 49.1%
B 98.4%
With AlCl3 or FeCl3 In chloroform reflux;A 36-46
B >97
1-naphthyl triflate
99747-74-7

1-naphthyl triflate

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With formic acid; triethylamine; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 65℃; for 12h;98%
With triethylammonium formate; palladium diacetate; 1,3-bis-(diphenylphosphino)propane In N,N-dimethyl-formamide at 18℃; for 0.8h; Product distribution; other catalysts, variation of temperature;92%
With lithium; nickel dichloride In tetrahydrofuran for 4h; Reduction; Heating;21%
Multi-step reaction with 3 steps
1.1: iron(II) acetate; N,N,N,N,-tetramethylethylenediamine; sodium t-butanolate; bis(pinacol)diborane / di-isopropyl ether / 120 °C
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C
2.2: 20 °C
3.1: C66H60BFeO2P4; N,N,N,N,-tetramethylethylenediamine; sodium t-butanolate / di-isopropyl ether; hexane; tetrahydrofuran / 15 h / 120 °C / Schlenk technique; Glovebox
View Scheme
trans-4-deuterio-1,4-dihydro-1-methoxynaphthalene
101916-87-4

trans-4-deuterio-1,4-dihydro-1-methoxynaphthalene

A

naphthalene
91-20-3

naphthalene

B

1-deuteronaphthalene
875-62-7

1-deuteronaphthalene

Conditions
ConditionsYield
With lithium diisopropyl amide In hexane for 0.5h; Product distribution; other solvents, bases;A 2%
B 98%
acetophenone
98-86-2

acetophenone

1-Chloronaphthalene
90-13-1

1-Chloronaphthalene

A

naphthalene
91-20-3

naphthalene

B

2-(naphthalen-1-yl)-1-phenylethan-1-one
16216-08-3

2-(naphthalen-1-yl)-1-phenylethan-1-one

Conditions
ConditionsYield
With sodium amalgam; potassium tert-butylate; ammonia for 2h;A n/a
B 98%
(naphthalene)Yb2(THF)3(NaCl)3

(naphthalene)Yb2(THF)3(NaCl)3

A

ytterbium(III) oxide

ytterbium(III) oxide

B

naphthalene
91-20-3

naphthalene

C

sodium chloride
7647-14-5

sodium chloride

Conditions
ConditionsYield
With air In tetrahydrofuran stirred for 18 h under dry air; centrifuged, washed with benzene and water (Yb2O3), naphthalene detd. by GLC in the organic layer, aq. soln. contains NaCl;A 98%
B 98%
C 96%
(naphthalene)Yb2(THF)3(NaCl)3

(naphthalene)Yb2(THF)3(NaCl)3

A

ytterbium(III) oxide

ytterbium(III) oxide

B

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With oxygen In tetrahydrofuran 18 h at room temp.;A 96%
B 98%
(1S,4S,5S,8S)-tetrabromo-1,2,3,4,5,6,7,8-octahydronaphthalene

(1S,4S,5S,8S)-tetrabromo-1,2,3,4,5,6,7,8-octahydronaphthalene

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
at 150℃; for 120h; Aromatisation;97%
1-naphthalenecarboxylic acid
86-55-5

1-naphthalenecarboxylic acid

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With triethylsilane; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In toluene at 160℃; for 15h; chemoselective reaction;97%
With water; palladium on activated charcoal at 250℃; under 30002.4 - 37503 Torr; for 14h;74%
With methanol at 40℃; for 48h; Schlenk technique; Irradiation; Inert atmosphere;70%
β-naphthaldehyde
66-99-9

β-naphthaldehyde

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With palladium nanoparticles supported on fibrous silica In cyclohexane at 130℃; for 20h; Molecular sieve;97%
With palladium diacetate In cyclohexane at 140℃; for 24h; Molecular sieve; air;82%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine In 1,4-dioxane at 110℃; for 48h; Inert atmosphere;95 %Chromat.
2-naphthyl pivalate
1503-86-2

2-naphthyl pivalate

naphthalene
91-20-3

naphthalene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); sodium formate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 140℃; for 24h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;97%
With bis(1,5-cyclooctadiene)nickel(0); 1,1,3,3-Tetramethyldisiloxane; tricyclohexylphosphine In toluene at 110℃; for 10h; Inert atmosphere;81 %Chromat.
With bis(1,5-cyclooctadiene)nickel(0); (dimethoxy)methylsilane; tricyclohexylphosphine In toluene at 80℃; for 12h; Inert atmosphere;99 %Chromat.
Multi-step reaction with 2 steps
1: toluene / 90 °C / Inert atmosphere; Schlenk technique
2: sodium formate / toluene / 24 h / 120 °C / Inert atmosphere; Schlenk technique
View Scheme
naphthalene
91-20-3

naphthalene

phthalic anhydride
85-44-9

phthalic anhydride

Conditions
ConditionsYield
With oxygen100%
With oxygen100%
With oxygen100%
naphthalene
91-20-3

naphthalene

A

phthalic anhydride
85-44-9

phthalic anhydride

B

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 340 - 360℃; Product distribution / selectivity;A 100%
B 0.05%
With oxygen at 340 - 360℃;A 100%
B 0.1%
With oxygen at 340 - 360℃;A 100%
B 0.02%
naphthalene
91-20-3

naphthalene

tetralin
119-64-2

tetralin

Conditions
ConditionsYield
With sodium; tert-butyl alcohol In tetrahydrofuran for 15h; Heating;100%
With Raney nickel; isopropyl alcohol at 82℃; for 1h; Temperature; Inert atmosphere;99%
With cobalt(II) chloride hexahydrate; lithium In tetrahydrofuran at 25℃; for 3h; Birch reaction; Inert atmosphere;98%
naphthalene
91-20-3

naphthalene

decalin
91-17-8

decalin

Conditions
ConditionsYield
With Ti8O8(14+)*6C8H4O4(2-)*4O(2-)*3.3Li(1+)*0.7Co(2+)*0.7C4H8O*0.7H(1-); hydrogen In neat (no solvent) at 120℃; under 37503.8 Torr; for 18h;100%
With hydrogen In cyclohexane at 100℃; under 33603.4 Torr; for 1h; Catalytic behavior; Temperature; Autoclave;99%
With nickel(II) oxide; hydrogen; palladium In hexane at 150℃; under 37503.8 Torr; for 36h;93%
naphthalene
91-20-3

naphthalene

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

3-chloro-1-(naphthalen-2-yl)propan-1-one
22422-70-4

3-chloro-1-(naphthalen-2-yl)propan-1-one

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 20℃; Cooling with ice;100%
With carbon disulfide; aluminium trichloride
With aluminium trichloride In nitrobenzene 1.) 5 h, room temp., 2.) 30 min, 40-45 deg C;
Stage #1: naphthalene; 2-chloropropionyl chloride With aluminum (III) chloride In nitrobenzene at 0℃;
Stage #2: With hydrogenchloride In nitrobenzene
naphthalene
91-20-3

naphthalene

tetranitromethane
509-14-8

tetranitromethane

1-Nitro-4-trinitromethyl-1,4-dihydro-naphthalene
146850-06-8

1-Nitro-4-trinitromethyl-1,4-dihydro-naphthalene

Conditions
ConditionsYield
In dichloromethane at 23℃; for 24h;100%
naphthalene
91-20-3

naphthalene

ethyl 2-chloro-2-methylthio-acetate
145628-18-8, 56078-31-0

ethyl 2-chloro-2-methylthio-acetate

ethyl α-methylthio-1-naphthaleneacetate
75286-85-0

ethyl α-methylthio-1-naphthaleneacetate

Conditions
ConditionsYield
tin(IV) chloride In dichloromethane for 0.666667h; Ambient temperature;100%
tin(IV) chloride In dichloromethane for 0.666667h; Ambient temperature; Yield given;
naphthalene
91-20-3

naphthalene

(1R,2S)-1,2-dihydronaphthalene-1,2-diol
51268-88-3

(1R,2S)-1,2-dihydronaphthalene-1,2-diol

Conditions
ConditionsYield
With toluene dioxygenase; oxygen Enzymatic reaction; regioselective reaction;100%
With toluene dioxygenase from Pseudomonas putida F1 variant A223V In ethanol at 30℃; for 0.5h; Enzymatic reaction; enantioselective reaction;62.7%
Pseudomonas putida UV4;
naphthalene
91-20-3

naphthalene

1,3-Dimethyl-6-chlorouracil
6972-27-6

1,3-Dimethyl-6-chlorouracil

6-methoxy-1,3-dimethyluracil
4097-20-5

6-methoxy-1,3-dimethyluracil

Conditions
ConditionsYield
In methanol at 20℃; for 1h; UV-irradiation;100%
naphthalene
91-20-3

naphthalene

(Cp*Ru)2(μ-NHPh)(μ-hydride)(μ-η2:η2-C7H8)

(Cp*Ru)2(μ-NHPh)(μ-hydride)(μ-η2:η2-C7H8)

[(Cp*Ru)2(μ-NHPh)(μ-H)(μ-η2:η2-naphthalene)]

[(Cp*Ru)2(μ-NHPh)(μ-H)(μ-η2:η2-naphthalene)]

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Inert atmosphere;100%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

naphthalene
91-20-3

naphthalene

exo-ethyl 2,3-benzo-2,4-norcaradiene-7-carboxylate

exo-ethyl 2,3-benzo-2,4-norcaradiene-7-carboxylate

Conditions
ConditionsYield
With Ag3(μ2-(3,5-(CF3)2PyrPy))3 In dichloromethane at 20℃; Buchner Ring Enlargement;100%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

naphthalene
91-20-3

naphthalene

ethyl 1a,7b-dihydro-1H-cyclopropa[a]naphthalene-1-carboxylate
13612-37-8

ethyl 1a,7b-dihydro-1H-cyclopropa[a]naphthalene-1-carboxylate

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 60℃; for 24h; Inert atmosphere;99%
With copper(II) sulfate at 150℃; for 4h;20%
at 140 - 145℃;
With rhodium (II) octanoate dimer In 1,2-dichloro-ethane at 25℃; for 0.333333h;55 %Spectr.
naphthalene
91-20-3

naphthalene

1-Nitronaphthalene
86-57-7

1-Nitronaphthalene

Conditions
ConditionsYield
With bismuth(III) nitrate; Montmorillonite KSF for 0.166667h; Nitration;99%
With benzyltriphenylphosphonium nitrate; Methanesulfonic anhydride at 20℃; for 0.333333h;99%
With In(OSO2CF3)3; nitric acid at 20 - 60℃; for 24h;98%
naphthalene
91-20-3

naphthalene

acetyl chloride
75-36-5

acetyl chloride

A

1'-naphthacetophenone
941-98-0

1'-naphthacetophenone

B

methyl 2-naphthyl ketone
93-08-3

methyl 2-naphthyl ketone

Conditions
ConditionsYield
aluminium trichloride In 1,2-dichloro-ethane at 0℃; Rate constant; Kinetics; Mechanism; other temperature; other concentrations;A 99%
B 1%
aluminium trichloride In 1,2-dichloro-ethane at 0℃; Thermodynamic data; ΔH<*>(activation); Σ<*>(activation);A 99%
B 1%
With aluminium trichloride; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 0℃; for 1h;A 89%
B 2%

91-20-3Relevant articles and documents

The role of matrix material and CCl4 (electron acceptor) on the ionization mechanisms of matrix-isolated naphthalene

Salama, F.,Allamandola, L.J.

, p. 6190 - 6191 (1991)

-

From Esters to Ketones via a Photoredox-Assisted Reductive Acyl Cross-Coupling Strategy

Chen, Yukun,Li, Weirong,Luo, Yixin,Qi, Xiaotian,Xi, Xiaoxiang,Xu, Minghao,Yuan, Weiming,Zhao, Hongping,Zheng, Songlin

, (2021/12/06)

A method was developed for ketone synthesis via a photoredox-assisted reductive acyl cross-coupling (PARAC) using a nickel/photoredox dual-catalyzed cross-electrophile coupling of two different carboxylic acid esters. A variety of aryl, 1°, 2°, 3°-alkyl 2-pyridyl esters can act as acyl electrophiles while N-(acyloxy)phthalimides (NHPI esters) act as 1°, 2°, 3°-radical precursors. Our PARAC strategy provides an alternative and reliable way to synthesize various sterically congested 3°-3°, 3°-2°, and aryl-3° ketones under mild and highly unified conditions, which have been otherwise difficult to access. The combined experimental and computational studies identified a Ni0/NiI/NiIII pathway for ketone formation.

Reduced Phenalenyl in Catalytic Dehalogenative Deuteration and Hydrodehalogenation of Aryl Halides

Singh, Bhagat,Ahmed, Jasimuddin,Biswas, Amit,Paira, Rupankar,Mandal, Swadhin K.

, p. 7242 - 7255 (2021/05/29)

Dehalogenative deuteration reactions are generally performed through metal-mediated processes. This report demonstrates a mild protocol for hydrodehalogenation and dehalogenative deuteration of aryl/heteroaryl halides (39 examples) using a reduced odd alternant hydrocarbon phenalenyl under transition metal-free conditions and has been employed successfully for the incorporation of deuterium in various biologically active compounds. The combined approach of experimental and theoretical studies revealed a single electron transfer-based mechanism.

Cross-Coupling Reactions of Aryl Halides with Primary and Secondary Aliphatic Alcohols Catalyzed by an O,N,N-Coordinated Nickel Complex

Hashimoto, Toru,Shiota, Keisuke,Funatsu, Kei,Yamaguchi, Yoshitaka

supporting information, p. 1625 - 1630 (2021/01/26)

A synthesis of alkyl aryl ethers was achieved via the cross-coupling of aryl halides with primary and secondary aliphatic alcohols catalyzed by a bench-stable nickel complex supported by a monoanionic O,N,N-tridentate ligand. This nickel-catalyzed reaction proceeds smoothly in the absence of a phosphine ligand, affording alkyl aryl ethers in moderate to good yields. (Figure presented.).

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