Naphthalene

Base Information

• Chemical Name: Naphthalene
• CAS No.: 91-20-3
• Deprecated CAS: 72931-45-4
• Molecular Formula: C10H8
• Molecular Weight: 128.174
• Hs Code.: 29029010
• European Community (EC) Number: 202-049-5,685-260-9
• ICSC Number: 0667
• NSC Number: 37565
• UN Number: 1334,2304
• UNII: 2166IN72UN
• DSSTox Substance ID: DTXSID8020913
• Nikkaji Number: J2.839H
• Wikipedia: Naphthalene
• Wikidata: Q179724
• NCI Thesaurus Code: C29839
• Metabolomics Workbench ID: 44039
• ChEMBL ID: CHEMBL16293
• Mol file: 91-20-3.mol

Synonyms:naphthalene

Chemical Property of Naphthalene

Chemical Property:

• Appearance/Colour: white to almost white crystals, crystalline flakes
• Vapor Pressure: 0.03 mm Hg ( 25 °C)
• Melting Point: 80-82 °C(lit.)
• Refractive Index: 1.632
• Boiling Point: 221.5 °C at 760 mmHg
• Flash Point: 78.9 °C
• PSA: 0.00000
• Density: 1.037 g/cm³
• LogP: 2.83980
• Storage Temp.: APPROX 4°C
• Solubility.: methanol: soluble50mg/mL, clear, colorless
• Water Solubility.: 30 mg/L (25 ºC)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 128.062600255
• Heavy Atom Count: 10
• Complexity: 80.6
• Transport DOT Label: Flammable Solid

Purity/Quality:

99% ^*data from raw suppliers

Naphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N, F, T
• Hazard Codes: Xn,N,F,T
• Statements: 22-40-50/53-67-65-38-11-39/23/24/25-23/24/25-52/53-20
• Safety Statements: 36/37-46-60-61-62-45-16-7-33-25-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Naphthalenes
• Canonical SMILES: C1=CC=C2C=CC=CC2=C1
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the blood. This may result in lesions of blood cells (haemolysis). The effects may be delayed. Ingestion could cause death. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the blood. This may result in chronic haemolytic anaemia. The substance may have effects on the eyes. This may result in development of cataract. This substance is possibly carcinogenic to humans.
• description: Naphthalene is a white solid chemical that vaporizes easily. It has a strong smell. You can sometimes smell naphthalene in the air or in water. Called white tar and tar camphor, naphthalene is used in mothballs and moth flakes. Petroleum and coal contain naphthalene. Naphthalene, the simplest of the fused or condensed ring hydrocarbon compounds composed of two benzene rings sharing two adjacent carbon atoms. Naphthalene is the most abundant single constituent of coal tar, a volatile product from the destructive distillation of coal, and is also formed in modern processes for the high-temperature cracking (breaking up of large molecules) of petroleum. 1-Methylnaphthalene and 2-methylnaphthalene are naphthalene-related compounds. 1-Methylnaphthalene is a clear liquid and 2-methylnaphthalene is a solid; both can be smelled in air and in water at very low concentrations. 1-Methylnaphthalene and 2-methylnaphthalene are used to make other chemicals such as dyes and resins. 2-Methylnaphthalene is also used to make vitamin K.
• Uses: In industry, naphthalene is used to manufacture a plastic called polyvinyl chloride (PVC). In public restrooms, naphthalene can be found in toilet deodorant blocks. At home, naphthalene can be found in moth repellents. Naphthalene balls are extensively used as household preservative of woolen clothes and as a deodorant tablet for the toilets, urinals, bathrooms etc. These are manufactured from naphthalene flakes by a tabletmaking machine having its ball shape die. Naphthalene is an important hydrocarbon raw material and is primarily used to manufacture phthalic anhydride and polyvinyl chloride (PVC) plastics, but is also used in moth repellents and toilet deodorant blocks. Naphthalene was used in liquid-phase exfoliation of graphite in organic solvents for the production of graphene sheets. It was used in preparation of carbon-coated Si 70 Sn 30 nanoparticles. It was used as fluorescent probe to study the aggregation behavior of sodium cholate. It was used to investigate influence of added short chain linear and branched alcohols on the binding of 1:1 complex of naphthalene and β-cyclodextrin. In addition to oxidation and reduction reactions, naphthalene readily undergoes substitutionreactions such as nitration, halogenation, sulfonation, and acylation to produce a varietyof other substances, which are used in the manufacture of dyes, insecticides, organic solvents,and synthetic resins. The principal use of naphthalene is for the production of phthalic anhydride,C8H4O3. Naphthalene is catalytically oxidized to phthalic anhydride: 2C10H8 + 9O2 → 2C4H8O3 +4CO2 + 4H2O using metal oxide catalysts. Phthalic anhydride is used to produce plastics,phthalate plasticizers, insecticides, pharmaceuticals, and resins. Sulfonation of naphthalene withsulfuric acid produces naphthalenesulfonic acids, which are used to produce naphthalene sulfonates.Naphthalene sulfonates are used in various formulations as concrete additives, gypsumboard additives, dye intermediates, tanning agents, and polymeric dispersants. Naphthalene isused to produce carbamate insecticides such as carbaryl, which is a wide-spectrum, generalpurposeinsecticide. Naphthalene occurs naturally in fossil fuels such as coal and petroleum. It is commonly produced from the distillation and fractionation of coal tar. Naphthalene is used as an intermediate in the production of phthalate plasticizers, other plastics and resins, and other products such as dyes, wood preservatives, explosives, lubricants, pharmaceuticals, deodorizers, and insect repellants. Moth balls and other moth repellants, and some solid block deodorizers used for toilets and diaper pails, are made of crystalline naphthalene (ATSDR, 2005).
• Description: Naphthalene occurs as transparent prismatic plates also available 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 is a commercially important aromatic hydrocarbon. Naphthalene occurs as a white solid or powder. 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. The primary use for naphthalene is in the production of phthalic anhydride, also of 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. Naphthalene is used in the production of phthalic anhydride; it is also used in mothballs. Naphthalene is also used in the manufacture of phthalic and anthranilic acids to make indigo, indanthrene, and triphenyl methane dyes, for synthetic resins, lubricant, celluloid, lampblack, smokeless powder, and hydronaphthalenes. Naphthalene is also used in dusting powders, lavatory deodorant discs, wood preservatives, fungicide, and as an insecticide. It has been used as an intestinal antiseptic and vermicide and in the treatment of pediculosis and scabies.

Technology Process of Naphthalene

There total 1853 articles about Naphthalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

1-Naphthylboronic acid (13922-41-3) → naphthalene (91-20-3,71998-51-1,72931-45-4) + 1-amino-naphthalene (134-32-7)

Guidance literature:

With copper(ll) sulfate pentahydrate; ammonia; water; sodium hydroxide; at 20 ℃; for 3h; under 760.051 Torr;

DOI:10.1139/V10-105

Reference yield: 32.8%

3-phenyl-propenal (104-55-2) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + benzo[b]selenophene (272-30-0) + naphthalene (91-20-3,71998-51-1,72931-45-4) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With dimethyl diselenide; In gas; at 630 ℃; Further byproducts given. Yields of byproduct given;

DOI:10.1007/BF02495651

Reference yield: 24.0%

1-Chloronaphthalene (90-13-1) → naphthalene (91-20-3,71998-51-1,72931-45-4) + 1-amino-naphthalene (134-32-7) + 1-amino-8-chloro-1,4-dihydronaphthalene

Guidance literature:

With benzene-1,3-dicarbonitrile; ammonia; In water; acetonitrile; for 7h; Irradiation;

DOI:10.1021/jo00381a009

upstream raw materials:

oxirane

tetralin

1,4-dioxane

2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl

Downstream raw materials:

1-naphthalenesulfonic acid

1-(2-naphthyl)-1-phenyl ethane

1-butylnaphthalene

methyl 2-naphthyl ketone

Refernces

• 1、 Cai, Xichen,Sakamoto, Masanori,Hara, Michihiro,Tojo, Sachiko,Kawai, Kiyohiko,Endo, Masayuki,Fujitsuka, Mamoru,Majima, Tetsuro. "Quenching processes of aromatic hydrocarbons in the higher triplet excited states-energy transfer vs. electron transfer". . p. 1735 - 1741. Retrieved 2004.
• 2、 Gao, Pengxiang,Liu, Qingbin,Liu, Yahuan,Ma, Ning,Wang, Zheng,Zhao, Ziwei. "Efficient base-free hydrodehalogenation of organic halides catalyzed by a well-defined diphosphine-ruthenium(II) complex". . . Retrieved 2021/10/29.
• 3、 Hashimoto, Toru,Shiota, Keisuke,Funatsu, Kei,Yamaguchi, Yoshitaka. "Cross-Coupling Reactions of Aryl Halides with Primary and Secondary Aliphatic Alcohols Catalyzed by an O,N,N-Coordinated Nickel Complex". supporting information. p. 1625 - 1630. Retrieved 2021/01/26.