Acenaphthene

Base Information

• Chemical Name: Acenaphthene
• CAS No.: 83-32-9
• Molecular Formula: C12H10
• Molecular Weight: 154.211
• Hs Code.: 29029080
• European Community (EC) Number: 201-469-6
• ICSC Number: 1674
• NSC Number: 7657
• UN Number: 3082,3077
• UNII: V8UT1GAC5Y
• DSSTox Substance ID: DTXSID3021774
• Nikkaji Number: J3.533E
• Wikipedia: Acenaphthene
• Wikidata: Q415103
• Metabolomics Workbench ID: 53872
• ChEMBL ID: CHEMBL1797271
• Mol file: 83-32-9.mol

Synonyms:acenaphthene

Chemical Property of Acenaphthene

Chemical Property:

• Appearance/Colour: white or pale yellow crystalline powder
• Vapor Pressure: 10 mm Hg ( 131 °C)
• Melting Point: 90-94 °C(lit.)
• Refractive Index: 1.6048
• Boiling Point: 278.999 °C at 760 mmHg
• Flash Point: 135.257 °C
• PSA: 0.00000
• Density: 1.043 g/cm³
• LogP: 2.93840
• Storage Temp.: APPROX 4°C
• Solubility.: chloroform: 50 mg/mL, clear
• Water Solubility.: 0.000347 g/100 mL
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 154.078250319
• Heavy Atom Count: 12
• Complexity: 155
• Transport DOT Label: Class 9

Purity/Quality:

99% ^*data from raw suppliers

Acenaphthene(1,2-DihydroAcenaphthylene) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, N, T, F, Xn
• Hazard Codes: Xi,N,T,F,Xn
• Statements: 36/37/38-50/53-39/23/24/25-23/24/25-11-52/53-67-65-38-51/53-20
• Safety Statements: 26-36/37/39-60-61-37/39-45-36/37-16-7-62-36-33-25-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1CC2=CC=CC3=C2C1=CC=C3
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Description: Acenaphthene is a tricyclic aromatic hydrocarbon and crystalline solid at ambient temperature. Acenaphthene does not dissolve in water but is soluble in many organic solvents. Acenaphthene is a component of crude oil and a product of combustion. Acenaphthene occurs in coal tar produced during the high-temperature carbonisation or coking of coal. It is used as a dye intermediate in the manufacture of some plastics and as an insecticide and fungicide. Acenaphthene is a component of crude oil and a product of combustion which may be produced and released to the environment during natural fires. Emissions from petroleum refining, coal tar distillation, coal combustion, and diesel-fuelled engines are major contributors of acenaphthene to the environment. Acenaphthene is an environmental pollutant and has been detected in cigarette smoke, automobile exhausts, and urban air; in effluents from petrochemical, pesticide, and wood preservative industries; and in soils, groundwater, and surface waters at hazardous waste sites. This compound is one among a number of polycyclic aromatic hydrocarbons (PAHs) on U.S. EPA’s (Environmental Protection Agency) priority pollutant list.
• Physical properties: White crystalline solid or orthorhombic bipyramidal needles from alcohol. Coal tar-like odor. The lowest odor threshold concentration in water that may result in rejection of contaminated water ranged from 0.02 to 0.22 ppm (Lillard and Powers, 1975). In Wisconsin, the taste and odor threshold concentration in water that is nontoxic to humans is 20 μg/L (ATSDR, 1995).
• Uses: Acenaphthene occurs in petroleum bottoms and is used as a dye intermediate, insecticide, and fungicide and in manufacturing plastics. Polycyclic aromatic hydrocarbons as carcinogenic Dye intermediate; manufacture of plastics; insecticide; fungicide.

Technology Process of Acenaphthene

There total 137 articles about Acenaphthene 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: 41.0%

acenaphthene quinone (82-86-0) → 1-acenaphthenol (6306-07-6) + acenaphthene (83-32-9) + acenaphthylene (208-96-8,25036-01-5)

Guidance literature:

With samarium diiodide; water; In tetrahydrofuran; at 20 ℃; for 0.00277778h;

DOI:10.1248/cpb.53.1017

Reference yield: 37.0%

C27H20N2O2 → (E)-1,2-diphenyl-ethene (103-30-0) + acenaphthene (83-32-9) + acenaphthylene (208-96-8,25036-01-5)

Guidance literature:

at 780 ℃; for 0.0833333h; under 1 Torr;

Reference yield: 31.0%

acenaphthene quinone (82-86-0) → decacyclene (191-48-0) + 1-acenaphthenol (6306-07-6) + acenaphthene (83-32-9) + acenaphthylene (208-96-8,25036-01-5)

Guidance literature:

bis(η⁶-biphenyl)titanium(0); In toluene; at 110 ℃; for 2h; Further byproducts given;

DOI:10.1055/s-1997-3209

upstream raw materials:

n-butyl magnesium bromide

phosgene

diethyl ether

3-bromoacenaphthene

Downstream raw materials:

acenaphthylene

5-bromoacenaphthene

2-(acenaphthene-5-carbonyl)-4-tert-butyl-benzoic acid

2-(acenaphthene-5-carbonyl)-3,6-dichloro-benzoic acid

Refernces

• 1、 Ouchi, Akihiko,Adam, Waldemar. "Laser-jet Photolysis of 1,8-Bis(substituted-methyl)naphthalenes: the Effect of Heteroatom Leaving Groups on the Two-photon C-C Bond Formation". . p. 628 - 629. Retrieved 1993.
• 2、 Platz, Matthew S.. "On the Mechanism of Intersystem Crossing and Ring Closure of the Triplet 1,8-Naphthoquinodimethane Biradical". . p. 1192 - 1194. Retrieved 1980.
• 3、 Van Loo, Marcia E.,Lugtenburg, Johan,Cornelisse, Jan. "Reactivity of the 5-hydroacenaphthylene anion towards electrophiles". . p. 1907 - 1914. Retrieved 1998.
• 4、 Ouchi, Akihiko,Yabe, Akira,Adam, Waldemar. "Highly efficient C - C bond formation in the two-photon chemistry of 1,8-bis(substituted-methyl)naphthalenes by direct excitation of photoactive leaving groups". . p. 6309 - 6312. Retrieved 1994.
• 5、 Adam, Waldemar,Ouchi, Akihiko. "Two-photon chemistry of 1,8-bis(bromomethyl)naphthalene in the laser-jet: Generation of acenaphthene by intramolecular C - C bond formation". . p. 1875 - 1878. Retrieved 1992.
• 6、 Goldstein,Glauser. "-". . p. 788. Retrieved 1934.
• 7、 Stegner, Philipp,F?rber, Christian,Zenneck, Ulrich,Knüpfer, Christian,Eyselein, Jonathan,Wiesinger, Michael,Harder, Sjoerd. "Metallic Barium: A Versatile and Efficient Hydrogenation Catalyst". supporting information. p. 4252 - 4258. Retrieved 2020/12/22.
• 8、 Bartulovich, Caroline O.,Boekell, Nicholas G.,Flowers, Robert A.,León-Pimentel, César Iván,Ramírez-Solís, Alejandro,Saint-Martin, Humberto. "Proton donor effects on the reactivity of SmI2. Experimental and theoretical studies on methanol solvationvs. Aqueous solvation". supporting information. p. 7897 - 7902. Retrieved 2020/06/26.