83-32-9

Basic information

• Product Name: Acenaphthene
• Synonyms: 1,2-dihydro-acenaphthylen;1,8-dihydroacenaphthalene;1,8-Ethylenenaphthalene1,2-Dihydroacenaphthylene;acenaphtene;Acenaphthcn;Acenaphthylene, 1,2-dihydro-;ethylenenaphthalene;NAPHTHYLENEETHYLENE
• CAS NO: 83-32-9
• Molecular Formula: C₁₂H₁₀
• Molecular Weight: 154.21
• EINECS: 201-469-6
• Product Categories: Aromatic Compounds;Aromatic Hydrocarbons (substituted) & Derivatives;Highly Purified Reagents;Other Categories;Zone Refined Products;A;AA to ALAnalytical Standards;A-BAlphabetic;Alpha Sort;Chemical Class;Naphthalenes;Volatiles/ Semivolatiles;AromaticsChemical Class;Hydrocarbons;NeatsAnalytical Standards;PAHs;Aromatics;Mutagenesis Research Chemicals;Arenes;Building Blocks;Chemical Synthesis;Organic Building Blocks;PAH
• Mol File: 83-32-9.mol
• Article Data: 71

Chemical Properties

• Melting Point: 90-94 °C(lit.)
• Boiling Point: 279 °C(lit.)
• Flash Point: 135 °C
• Appearance: brown-beige/crystalline
• Density: 1.06
• Vapor Density: 5.32 (vs air)
• Vapor Pressure: 10 mm Hg ( 131 °C)
• Refractive Index: 1.6048
• Storage Temp.: APPROX 4°C
• Solubility: chloroform: 50 mg/mL, clear
• Water Solubility: 0.000347 g/100 mL
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,28
• BRN: 386081
• CAS DataBase Reference: Acenaphthene(CAS DataBase Reference)
• NIST Chemistry Reference: Acenaphthene(83-32-9)
• EPA Substance Registry System: Acenaphthene(83-32-9)

Safety Data

• 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
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: AB1000000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 83-32-9(Hazardous Substances Data)

Usage

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.

Chemical Properties

Different sources of media describe the Chemical Properties of 83-32-9 differently. You can refer to the following data:
1. Acenaphthene is a tricyclic aromatic hydrocarbon, crystalline solid at ambient tempera- ture. Acenaphthene does not dissolve in water, but is soluble in many organic solvents. Acenaphthene occurs in coal tar produced during high temperature carbonization or cok- ing 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 that may be produced and released into the environment during natural fi res. Emissions from petroleum refi ning, coal tar distillation, coal combustion, and diesel- fueled 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 effl uents from petrochemical, pesticide, and wood preservative industries; and in soils, groundwater, and surface waters at hazardous waste sites. This compound is one of a number of polycyclic aromatic hydrocarbons on the US EPA’s prior- ity pollutant list.
2. Acenaphthene is a white combustible, crystalline solid. PAHs are compounds containing multiple benzene rings and are also called polynuclear aromatic hydrocarbons
3. white or pale yellow crystalline powder

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

Different sources of media describe the Uses of 83-32-9 differently. You can refer to the following data:
1. Acenaphthene occurs in petroleum bottoms and is used as a dye intermediate, insecticide, and fungicide and in manufacturing plastics.
2. Polycyclic aromatic hydrocarbons as carcinogenic
3. Dye intermediate; manufacture of plastics; insecticide; fungicide.

Definition

Different sources of media describe the Definition of 83-32-9 differently. You can refer to the following data:
1. ChEBI: A polycyclic aromatic hydrocarbon derived from naphthalene by the addition of an ethylene bridge connecting C-1 and C-8.
2. A colorless crystalline derivative of naphthalene, used in producing some dyes.
3. acenaphthene: A colourless crystallinearomatic compound, C12H10;m.p. 95°C; b.p. 278°C. It is an intermediatein the production of somedyes.

Synthesis Reference(s)

Synthetic Communications, 14, p. 1119, 1984 DOI: 10.1080/00397918408059644

General Description

White needles. Melting point 93.6°C. Soluble in hot alcohol. Denser than water and insoluble in water. Hence sinks in water. May irritate skin and mucous membranes. Emits acrid smoke and irritating fumes when heated to decomposition. Derived from coal tar and used to make dyes, pharmaceuticals, insecticides, fungicides, and plastics.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Acenaphthene is incompatible with strong oxidizing agents. Incompatible with ozone and chlorinating agents. Forms crystalline complexes with desoxycholic acid .

Health Hazard

Different sources of media describe the Health Hazard of 83-32-9 differently. You can refer to the following data:
1. Carcinogenicity of acenaphthene in animalsis not established. Tests for mutagenicity havegiven inconclusive results.
2. Exposures to acenaphthene cause poisoning and include symptoms such as irritation to the skin, eyes, mucous membranes, and upper respiratory tract. Studies on labora- tory animals orally exposed to acenaphthene showed loss of body weight, peripheral blood changes (unspecifi ed), increased aminotransferase levels in blood serum, and mild morphological damage to the liver and kidneys. In chronic exposures, acenaph- thene is known to cause damage to the kidneys and liver. Acenaphthene is irritating to the skin and mucous membranes of humans and animals. Oral exposure of rats to ace- naphthene for 32 days produced peripheral blood changes, mild liver and kidney dam- age, and pulmonary effects. However, detailed studies with acenaphthene in humans are limited.

Fire Hazard

Flash point data for Acenaphthene are not available. Acenaphthene is probably combustible.

Safety Profile

Moderately toxic by intraperitonealroute. Mutation data reported.Incompatible with strongoxidizing agents, ozone, chlorinating agents. When heatedto decomposition it emits acrid smoke and irritating vapors.

Potential Exposure

Acenaphthene occurs naturally in coal tar and in coal tar produced during the high-temperature carbonization or coking of coal; coal tar distilling; petroleum processing; shale oil processing. It is used as an intermediate for dyes, fungicides, insecticides, herbicides, pharmaceuticals, plant growth hormones; 1,8 naphthalic acid; in the manufacture of some plastics; and has been detected in cigarette smoke and gasoline exhaust condensates; a constituent of coal tar creosote, asphalt, and diesel fuel. It has been used as an polyploidy agent.

Source

Detected in groundwater beneath a former coal gasification plant in Seattle, WA at a concentration of 180 g/L (ASTR, 1995). Acenaphthene is present in tobacco smoke, asphalt, combustion of aromatic fuels containing pyridine (quoted, Verschueren, 1983). Acenaphthene was detected in asphalt fumes at an average concentration of 18.65 ng/m3 (Wang et al., 2001). Present in diesel fuel and corresponding aqueous phase (distilled water) at concentrations of 100 to 600 mg/L and 4 to 14 g/L, respectively (Lee et al., 1992). Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 625. Average acenaphthene concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 1, 2, and 6 g/L, respectively. Acenaphthene occurs naturally in coal tar. Based on laboratory analysis of 7 coal tar samples, acenaphthene concentrations ranged from 350 to 12,000 ppm (EPRI, 1990). Detected in 1-yr aged coal tar film and bulk coal tar at concentrations of 5,800 and 5,900 mg/kg, respectively (Nelson et al., 1996). A high-temperature coal tar contained acenaphthene at an average concentration of 1.05 wt % (McNeil, 1983). Lee et al. (1992a) equilibrated 8 coal tars with distilled water at 25 °C. The maximum concentration of acenaphthene observed in the aqueous phase was 0.3 mg/L. Nine commercially available creosote samples contained acenaphthene at concentrations ranging from 9,500 to 110,000 mg/kg (Kohler et al., 2000). Acenaphthene was detected in a diesel-powered medium duty truck exhaust at an emission rate of 19.3 μg/km (Schauer et al., 1999) and is a component in cigarette smoke. Acenaphthene was detected in soot generated from underventilated combustion of natural gas doped with 3 mole % toluene (Tolocka and Miller, 1995). Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 6.55 and 177 μg/km, respectively (Schauer et al., 2002). Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rates of acenaphthene were 2.02 mg/kg of pine burned, 1.15 mg/kg of oak burned, and 0.893 mg/kg of eucalyptus burned. Under atmospheric conditions, a low rank coal (0.5–1 mm particle size) from Spain was burned in a fluidized bed reactor at seven different temperatures (50 °C increments) beginning at 650 °C. The combustion experiment was also conducted at different amounts of excess oxygen (5 to 40%) and different flow rates (700 to 1,100 L/h). At 20% excess oxygen and a flow rate of 860 L/h, the amount of acenaphthene emitted ranged from 1,272.4 ng/kg at 650 °C to 6,800.0 ng/kg at 750 °C. The greatest amount of PAHs emitted was observed at 750 °C (Mastral et al., 1999). Typical concentration of acenaphthene in a heavy pyrolysis oil is 1.6 wt % (Chevron Phillips, May 2003).

Environmental fate

Biological. When acenaphthene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with rapid adaptation was observed. At concentrations of 5 and 10 mg/L, 95 and 100% biodegradation, respectively, were observed after 7 d (Tabak et al., 1981). A Beijerinckia sp. and a mutant strain (Beijerinckia sp. strain B8/36) cooxidized acenaphthene to the following metabolites: 1,2-acenaphthenediol, acenaphthene-quinone, and a compound tentatively identified as 1,2-dihydroxyacenaphthylene (Schocken and Gibson, 1984). The fungus Cunninghamella elegans ATCC 36112 degraded approximately 64% acenaphthene added within 72 h of incubation. Metabolites identified and their respective yields were 6-hydroxyacenaphthenone (24.8%), 1,2-acenaphthenedione (19.9%), trans-1,2-dihydroxyacenaphthene (10.3%), 1,5-dihydroxyacenaphthene (2.7%), 1-acenaphthenol (2.4%), 1-acenaphthenone (2.1%), and cis-1,2-dihydroxyacenaphthene (1.8%) (Pothuluri et al., 1992). A recombinant strain of Pseudomonas aeruginosa PAO1(pRE695) degraded acenaphthene via mono-oxygenation to 1-acenaphthenol which was converted to 1-acenaphthenone and cis- and trans-1,2-dihydroxyacenaphthenes. The two latter compounds were subsequently converted to 1,2- acenaphthoquinone which oxidized to naphthalene-1,8-dicarboxylic acid (Selifonov et al., 1996). In a soil-water system, acenaphthene did not biodegrade under anaerobic conditions. Under denitrification conditions, acenaphthene (water concentration 400 μg/L) degraded to nondetectable levels in 40 d. In both studies, the acclimation period was approximately 2 d (Mihelcic and Luthy, 1988). Photolytic. Fukuda et al. (1988) studied the photodegradation of acenaphthene and alkylated naphthalenes in distilled water and artificial seawater using a high-pressure mercury lamp. Based upon a rate constant of 0.23/h, the photolytic half-life of acenaphthene in water is 3 h. Behymer and Hites (1985) determined the effect of different substrates on the rate of photooxidation of acenaphthene using a rotary photoreactor equipped with a 450-W medium pressure mercury lamp (λ = 300–410 nm). The photolytic half-lives of acenaphthene absorbed onto silica gel, alumina, and fly ash were 2.0, 2.2, and 44 h, respectively. The estimated photooxidation half-life of acenaphthene in the atmosphere via OH radicals is 0.879 to 8.79 h (Atkinson, 1987). Chemical/Physical. Ozonation in water at 60 °C produced 7-formyl-1-indanone, 1-indanone, 7- hydroxy-1-indanone, 1-indanone-7-carboxylic acid, indane-1,7-dicarboxylic acid, and indane-1- formyl-7-carboxylic acid (Chen et al., 1979). Wet oxidation of acenaphthene at 320 °C yielded formic and acetic acids (Randall and Knopp, 1980). The measured rate constant for the gas-phase reaction of acenaphthene with OH radicals is 8.0 x 10-11 cm3/molecule·sec (Reisen and Arey, 2002).

Purification Methods

It has also been purified by chromatography from CCl4 on alumina with *benzene as eluent [McLaughlin & Zainal J Chem Soc 2485 1960]. [Beilstein 5 IV 1834.]

Incompatibilities

Ozone and strong oxidizing agents, including perchlorates, chlorine, fluorine, and bromine

Waste Disposal

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. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Incineration or permanganate oxidation

InChI:InChI=1/C10H8.C2H4/c1-2-6-10-8-4-3-7-9(10)5-1;1-2/h1-8H;1-2H2

Synthetic route

acenaphthylene (208-96-8) → acenaphthene (83-32-9)

Conditions	Yield
With tetraethylammonium bromide In ethanol at 60℃; electrolysis, lead cathode;	100%
With benzenetellurol In ethanol; ethyl acetate for 4h; Product distribution; Heating; other reagent, reaction time;	98%
With iodine; hypophosphorous acid In acetic acid for 24h; Heating;	98%

acenaphthylene + 1,4,4a,9a-tetrahydro-fluorene (52652-40-1) → 9H-fluorene (86-73-7) + acenaphthene (83-32-9)

Conditions	Yield
palladium on activated carbon at 250℃; for 2h;	A 93% B 90%

1,8-bis(bromomethyl)naphthalene (2025-95-8) → acenaphthene (83-32-9)

Conditions	Yield
With hexamethyldistannane; palladium In toluene at 110℃; for 18h;	90%
With norborn-2-ene; benzophenone In acetonitrile Irradiation;	8.1%
With phenyllithium; benzene

1,2,3,4-tetrahydro-9H-fluorene (17057-95-3) + acenaphthylene (208-96-8) → 9H-fluorene (86-73-7) + acenaphthene (83-32-9)

Conditions	Yield
	A n/a B 90%

5-bromoacenaphthene (2051-98-1) → 1,1',2,2'-tetrahydro-5,5'-biacenaphthylene (41908-42-3) + acenaphthene (83-32-9)

Conditions	Yield
With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl-formamide at 70℃; for 3h; Dimerization; dehalogenation;	A 85% B 5%
With 9,10-phenanthroline; nickel dichloride; zinc In N,N-dimethyl-formamide at 70℃; for 3h; Dehalogenation; dimerization;	A 71% B 15%
Stage #1: 5-bromoacenaphthene With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl-formamide at 70℃; for 6h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 30 - 40℃; for 0.5h; Title compound not separated from byproducts;	A 95 % Chromat. B 5 % Chromat.

5-bromoacenaphthene (2051-98-1) → acenaphthene (83-32-9)

Conditions	Yield
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 2h;	81%

acetic anhydride (108-24-7) + acenaphthylene (208-96-8) → 5-ethylacenaphthene (13936-05-5) + 1-acenaphthen-3-yl-ethanone (7434-96-0) + 5-acetylacenaphthene (10047-18-4) + acenaphthene (83-32-9)

Conditions	Yield
With iodine; hypophosphorous acid In acetic acid for 24h; Heating;	A 5% B 40% C 3% D 52%

5-bromoacenaphthene (2051-98-1) + carbon monoxide (201230-82-2) → acenaphthene-5-carboxylic acid (55720-22-4) + acenaphthene (83-32-9)

Conditions	Yield
With dicobalt octacarbonyl; potassium carbonate; methyloxirane In methanol at 60℃; under 760 Torr; for 6h;	A 50% B n/a

4-chloro-n-butyric anhydride (20496-01-9) + acenaphthylene (208-96-8) → acenaphthene (83-32-9) + 1-Acenaphthen-1-yl-4-chloro-butan-1-one (88970-55-2) + 4-Chloro-butyric acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester + 1(2H)-acenaphthylenone (2235-15-6)

Conditions	Yield
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given;	A 6% B 46% C n/a D 8.5%
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given;	A 6% B 46% C 8.5% D 8.5%

4-chloro-n-butyric anhydride (20496-01-9) + acenaphthylene (208-96-8) → acenaphthene (83-32-9) + 1-Acenaphthen-1-yl-4-chloro-butan-1-one (88970-55-2) + 4-Chloro-butyric acid 1-[2H-acenaphthylen-(1E)-ylidene]-4-chloro-butyl ester + 1(2H)-acenaphthylenone (2235-15-6)

Conditions	Yield
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given;	A 6% B 46% C 3.5% D 8.5%

acetic anhydride (108-24-7) + acenaphthylene (208-96-8) → acenaphthene (83-32-9) + Acetic acid 1-[2H-acenaphthylen-(1Z)-ylidene]-ethyl ester + Acetic acid 1-[2H-acenaphthylen-(1E)-ylidene]-ethyl ester + 1(2H)-acenaphthylenone (2235-15-6)

Conditions	Yield
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given;	A 9% B 43% C 18% D n/a

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

Conditions	Yield
at 780℃; under 1 Torr; for 0.0833333h;	A 43% B 19% C 37%

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

Conditions	Yield
With samarium diiodide; water In tetrahydrofuran at 20℃; for 0.00277778h;	A 41% B 26% C 23%

C20H15N2O4S(1-)*Li(1+) → acenaphthene (83-32-9) + 9-Hydroxymethyl-1H-naphtho[1,2-c]furan-3-one (182313-44-6) + acenaphthylene (208-96-8)

Conditions	Yield
at 730℃; under 0.03 Torr; for 0.05h;	A 9% B 38% C 12%

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

Conditions	Yield
bis(η6-biphenyl)titanium(0) In toluene at 110℃; for 2h; Further byproducts given;	A 21% B 10% C 11% D 31%

carbon dioxide (124-38-9) + acenaphthylene (208-96-8) + methyl iodide (74-88-4) → acenaphthene (83-32-9) + trans-1,2-dicarbomethoxy-1,2-dihydroacenaphthylene (5673-04-1, 5673-22-3, 51869-93-3, 56137-60-1, 93012-10-3) + Acetic acid 1-[2H-acenaphthylen-(1E)-ylidene]-ethyl ester + 1(2H)-acenaphthylenone (2235-15-6)

Conditions	Yield
1.) electrolysis at -1.7 V (0.1 M TBAI), DMF, -35 deg C; 2) overnight; Yield given. Multistep reaction. Further byproducts given;	A 9% B n/a C 18% D n/a

1,8-bis(phenylselenomethyl)-naphthalene → acenaphthene (83-32-9)

Conditions	Yield
With benzophenone In acetonitrile Irradiation;	12.3%
In cyclohexane Irradiation; with a KrF (248 nm) excimer laser;
In cyclohexane Irradiation;

4-chloro-n-butyric anhydride (20496-01-9) + acenaphthylene (208-96-8) → acenaphthene (83-32-9) + Cyclopropanecarboxylic acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester + 4-Chloro-butyric acid [2H-acenaphthylen-(1E)-ylidene]-cyclopropyl-methyl ester + 4-Chloro-butyric acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

Conditions	Yield
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given;	A 9% B 3% C 4% D 11%

1,8-bis(phenylthiomethyl)-naphthalene (97840-91-0) → acenaphthene (83-32-9)

Conditions	Yield
With benzophenone In acetonitrile Irradiation;	5.5%
In cyclohexane Irradiation; with a KrF (248 nm) excimer laser;	72 % Spectr.
In cyclohexane Irradiation;

n-butyl magnesium bromide (693-03-8) + phosgene (75-44-5) + diethyl ether (60-29-7) + 3-bromoacenaphthene (5209-31-4) → acenaphthene (83-32-9)

naphthalene (91-20-3) + ethene (74-85-1) → acenaphthene (83-32-9)

Conditions	Yield
bei Rotglut;

naphthalene (91-20-3) + ethene (74-85-1) → 2,2'-binaphthalene (612-78-2) + phenanthrene (85-01-8) + acenaphthene (83-32-9)

Conditions	Yield
beim Leiten durch ein gluehendes Rohr;

1,2,2a,3,4,5-hexahydro-acenaphthylene (480-72-8) → acenaphthene (83-32-9)

Conditions	Yield
With sulfur at 180℃;

cis-acenaphthene-1,2-diol (2963-86-2) → (+/-)-(2aξH)-2a.3.4.5-tetrahydro-acenaphthenediol-(1r.2c) (16897-64-6) + acenaphthene (83-32-9)

Conditions	Yield
With hydrogenchloride; ethanol; iron(III) chloride at 50℃; Hydrogenation.weiteres Reagens: Platin;

1(2H)-acenaphthylenone oxime (5088-53-9) → acenaphthene (83-32-9)

Conditions	Yield
With acetic acid; zinc

(+/-)-cis-1,2,2a,3,4,5-hexahydro-acenaphthylene-3-carboxylic acid → 1,2-dihydroacenaphthylene-3-carboxylic acid (7424-63-7) + acenaphthene (83-32-9)

Conditions	Yield
With palladium on activated charcoal

(+/-)-trans-1,2,2a,3,4,5-hexahydro-acenaphthylene-3-carboxylic acid → 1,2-dihydroacenaphthylene-3-carboxylic acid (7424-63-7) + acenaphthene (83-32-9)

Conditions	Yield
With palladium on activated charcoal

(8-carboxy-[1]naphthyl)-glyoxylic acid (861597-33-3) → acenaphthene (83-32-9)

Conditions	Yield
With phosphorus; hydrogen iodide

acenaphthene-1,5-dicarboxylic acid (51869-97-7, 51869-99-9) → acenaphthene-5-carboxylic acid (55720-22-4) + acenaphthene (83-32-9)

Conditions	Yield
at 280℃;

acenaphthene-1,2-dione disemicarbazone + sodium ethanolate (141-52-6) → acenaphthene (83-32-9)

Conditions	Yield
at 200℃; im Rohr;

acenaphthene (83-32-9) → decahydroacenaphthene (2146-36-3)

Conditions	Yield
	100%
aluminum nickel	100%
Rh/C	100%

acenaphthene (83-32-9) → 9,9,10,10-tetradeuteroacenaphthene tetradeuteroacenaphthene (16333-90-7)

Conditions	Yield
With dimethylsulfoxide-d6; sodium hydride at 78℃; for 22h;	100%
With sodium dimsylate-d5; dimethylsulfoxide-d6 at 75℃; for 20h;
With water-d2; sodium hydride In dimethylsulfoxide-d6	99.8 %Spectr.
With dimethylsulfoxide-d6; sodium hydride

acenaphthene (83-32-9) → phthalic anhydride (85-44-9)

Conditions	Yield
With oxygen at 300 - 330℃;	100%
With oxygen at 300 - 330℃;	100%
With oxygen at 300 - 330℃;	100%

acenaphthene (83-32-9) → (2aR,5aα,8aR,8bα)-dodecahydro-acenaphthylene

Conditions	Yield
With hydrogen; palladium 10% on activated carbon at 130℃; under 3000.3 - 7500.75 Torr; for 4 - 10h; Product distribution / selectivity;	99.5%

acenaphthene (83-32-9) → 5-bromoacenaphthene (2051-98-1)

Conditions	Yield
With cerium(III) chloride heptahydrate; dihydrogen peroxide; acetic acid; sodium bromide In water at 20℃; for 3h; Reagent/catalyst; Temperature;	97.5%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 3h;	97%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃;	96%

chloro-trimethyl-silane (75-77-4) + acenaphthene (83-32-9) → 4,5,7,8-tetrakis(trimethylsilyl)-4,5,7,8-tetrahydroacenaphthene (80262-78-8)

Conditions	Yield
With lithium In tetrahydrofuran at 0 - 5℃;	97%

acenaphthene (83-32-9) → 4-nitroacenaphthene (602-87-9)

Conditions	Yield
With Iron(III) nitrate nonahydrate; acetic acid at 35℃; for 5h; Reagent/catalyst; Temperature;	96%
With bismuth(III) nitrate; acetic anhydride; acetic acid at 20℃; for 6h; Reagent/catalyst; Temperature;	96.5%
With nitric acid In dichloromethane at 10℃; for 1.33333h;	90%

acenaphthene (83-32-9) → 1,2,2a,3,4,5-hexahydro-acenaphthylene (480-72-8)

Conditions	Yield
With hydrogen In n-heptane at 150 - 200℃; under 15001.5 Torr; for 1h; Autoclave;	96.2%
With Raney Ni-Al In potassium hydroxide; water at 90℃; for 6.5h; Reduction;	93%
With cobalt(II) chloride hexahydrate; lithium In tetrahydrofuran at 25℃; for 2h; Birch reaction; Inert atmosphere; regioselective reaction;	88%

acenaphthene (83-32-9) + 7,7',8,8'-tetracyanoquinodimethane (1518-16-7) → 9-Acenaphthyl<4-(dicyanomethyl)phenyl>dicyanomethane (77074-97-6) + acenaphthylene (208-96-8)

Conditions	Yield
for 0.0833333h; Heating;	A 95.5% B n/a

chloral hydrate (302-17-0) + acenaphthene (83-32-9) → 1,1,1-trichloro-2,2-di(acenaphth-4-yl)ethane (22010-44-2)

Conditions	Yield
With sulfuric acid In chloroform 1.) 20 deg C, 1 h, 2.) 25 deg C, 3 h;	94%

N-Bromosuccinimide (128-08-5) + acenaphthene (83-32-9) → 5-bromoacenaphthene (2051-98-1)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 3h;	93.6%

acenaphthene (83-32-9) → 1,8-Naphthalic anhydride (81-84-5)

Conditions	Yield
With sodium dichromate	92%
With copper(II) acetate dihydrate; manganese(II) acetate dihydrate; oxygen; acetic acid; potassium bromide at 105℃;	90%
With sodium dichromate In acetic acid at 75℃; for 8h;	80%

2,2-bis(4-chlorocarbonylphenyl)-hexafluoropropane (1102-92-7) + acenaphthene (83-32-9) → (4-{1-[4-(Acenaphthene-5-carbonyl)-phenyl]-2,2,2-trifluoro-1-trifluoromethyl-ethyl}-phenyl)-acenaphthen-5-yl-methanone (107508-65-6)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane 1.) 0 -> 60 deg C, 2 h, 2.) 60 deg C, 1 h;	92%

1,2,4,5-tetracyanobenzene (712-74-3) + acenaphthene (83-32-9) → 5-(acenapthen-1-yl)benzene-1,2,4-tricarbonitrile (138905-02-9) + 4,6-di(acenaphthen-1-yl)benzene-1,3-dicarbonitrile (138905-03-0) + acenaphthene quinone (82-86-0)

Conditions	Yield
In acetonitrile for 12h; Product distribution; Mechanism; Irradiation; other solvents, irradiation at different wave-length;	A 90% B 1.5% C n/a
In acetonitrile for 12h; Irradiation;	A 90% B 1.5% C 2 mg

acenaphthene (83-32-9) + trifluoromethanesulphonyloxy-methylene-N,N-dimethyliminium trifluoromethanesulphonate (132407-64-8) → acenaphthene-5-carbaldehyde (5345-46-0)

Conditions	Yield
In chloroform at 130℃; for 72h;	90%

1,8-bis(2,6-dichlorophenylethynyl)naphthalene (1336881-66-3) + acenaphthene (83-32-9) → 7,14-bis(2,6-dichlorophenyl)acenaphtho[1,2-k]fluoranthene (1422960-20-0)

Conditions	Yield
Stage #1: 1,8-bis(2,6-dichlorophenylethynyl)naphthalene; acenaphthene With tris(triphenylphosphine)rhodium(l) chloride In 5,5-dimethyl-1,3-cyclohexadiene at 110℃; for 60h; Inert atmosphere; Sealed tube; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 110℃; Inert atmosphere; Sealed tube;	90%

acenaphthene (83-32-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 1,2-dihydroacenaphthylene-3-carbaldehyde (92378-92-2)

Conditions	Yield
With silica gel; trichlorophosphate for 0.025h; Formylation; Microwave irradiation (300 W);	89%

acenaphthene (83-32-9) + 4-methoxy-benzoyl chloride (100-07-2) → 5-(p-methoxybenzoyl)acenaphthene

Conditions	Yield
With aluminum (III) chloride In 1,1,2,2-tetrachloroethane at 20℃;	87%
With carbon disulfide; aluminium trichloride

acenaphthene (83-32-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → acenaphthene-5-carbaldehyde (5345-46-0)

Conditions	Yield
With trichlorophosphate at 90 - 95℃; for 3h; Vilsmeier Reaction;	85%
With trichlorophosphate at 70℃; for 3h;	57%
With trichlorophosphate at 90 - 95℃; for 3.33h;	46.74%

acenaphthene (83-32-9) → 1,2-dibromoacenaphthylene (13019-33-5)

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4h; Inert atmosphere; Reflux;	84%
With N-Bromosuccinimide; benzoic acid anhydride
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2h; Reflux;
With N-Bromosuccinimide

acenaphthene (83-32-9) → 1(2H)-acenaphthylenone (2235-15-6)

Conditions	Yield
With tert.-butylhydroperoxide; V2O5/TiO2 In water at 80℃; for 8h; Sealed tube; Green chemistry;	82%
With potassium permanganate; sulfuric acid; triethylamine In chloroform Ambient temperature;	76%
With tetrakis(pyridine)silver(II) peroxodisulfate In acetonitrile for 1h; Heating;	60%

acenaphthene (83-32-9) → acenaphthene quinone (82-86-0)

Conditions	Yield
With benzeneseleninic anhydride In chlorobenzene at 120℃; for 24h;	81%
With sodium dichromate; acetic acid ; cerium (IV)-acetate; acetic acid at 40℃; Reagens 4: CeCl3;
With ammonium dichromate; acetic acid at 100℃;

acenaphthene (83-32-9) + p-toluenesulfonyl chloride (98-59-9) → acenaphthen-5-yl-p-tolyl sulfone (80464-89-7)

Conditions	Yield
With tin(IV) chloride at 140℃;	80%
With tin(IV) chloride

acenaphthene (83-32-9) → acenaphthylene (208-96-8)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 24h; Reflux;	80%
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 120℃; under 9750.98 Torr; for 8h;	77%
With manganese(IV) oxide In benzene for 30h; Heating;	41%

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 75-44-5 phosgene 
• 60-29-7 diethyl ether 
• 5209-31-4 3-bromoacenaphthene 
• 91-20-3 naphthalene 
• 74-85-1 ethene 
• 480-72-8 1,2,2a,3,4,5-hexahydro-acenaphthylene 
• 2025-95-8 1,8-bis(bromomethyl)naphthalene 
• 2963-86-2 cis-acenaphthene-1,2-diol 
• 5088-53-9 1(2H)-acenaphthylenone oxime 
• 861597-33-3 (8-carboxy-[1]naphthyl)-glyoxylic acid 
• 51869-97-7 acenaphthene-1,5-dicarboxylic acid 
• 141-52-6 sodium ethanolate 
• 208-96-8 acenaphthylene 

Downstream Products

• 2051-98-1 5-bromoacenaphthene 
• 16294-60-3 4-acenaphthen-5-yl-4-oxo-butyric acid 
• 36440-49-0 γ-carbonyl-3-acenaphthene butyric acid 
• 208-96-8 acenaphthylene 
• 4578-98-7 5,10-Dihydro-acepleiaden-5,10-dion 
• 4623-31-8 2-(acenaphthene-5-carbonyl)-benzoic acid 
• 855201-87-5 2-(acenaphthene-5-carbonyl)-4-tert-butyl-benzoic acid 
• 115895-75-5 2-(acenaphthene-5-carbonyl)-3,6-dichloro-benzoic acid 
• 102170-76-3 2-(acenaphthene-5-carbonyl)-3,4,5,6-tetrabromo-benzoic acid 
• 102170-82-1 2-(acenaphthene-5-carbonyl)-3,4,5,6-tetrachloro-benzoic acid 
• 55720-25-7 5-propionylacenaphthene 
• 10047-18-4 5-acetylacenaphthene 
• 28445-09-2 naphthalene-1,4,5-tricarboxylic acid 
• 5345-46-0 acenaphthene-5-carbaldehyde 

Relevant articles and documents

Time-delayed, two-color excimer laser photolysis of 1,8-bis(substituted-methyl)naphthalenes with group 16 atom leaving groups

Time-delayed, two-color photolysis of 1,8-bis(phenoxymethyl)-(1a), 1,8-bis(phenylthiomethyl)-(1b), and 1,8-bis(phenylselenomethyl)-naphthalene (1c) was conducted by successive irradiation of XeCl (308 nm) and XeF (351 nm) excimer lasers. The yield of the two-photon product, acenaphthene 3, was strongly dependent on the delay time and showed two maxima at different delay times.

Time-delayed, Two-color Excimer Laser Photolysis of 1,8-Bis(halomethyl)naphthalenes

Time-delayed two-color photolysis of 1,8-bis(bromomethyl)-naphthalene and 1,8-bis(chloromethyl)naphthalene was conducted by successive irradiation of XeCl (308 nm) and XeF (351 nm) excimer lasers.Increase in the yield of the two-photon product, acenaphthene, strongly depended on the delay time of the two lasers and showed two maxima at the delay times of 0-30 ns and 0.2-0.5 μs.

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A laser-specific C-C bond formation of bichromophoric compounds

The formation of acenaphthene from less photoreactive 1,8-bis(bromomethyl)naphthalene and 1,8-bis(chloromethyl)naphthalene by high-fluence KrF excimer laser irradiation was observed; the result contrasts with failed attempts using a low-pressure mercury lamp.

A remarkable wavelength dependence on the laser-induced two-photon C-C bond formation

Two-photon intramolecular C-C bond formation of 1,8-bis(bromomethyl)naphthalene and 1,8-bis(chloromethyl)naphthalene by high fluence excimer laser irradiations showed a considerable wavelength dependence on the conversion, the efficiency, and the yield of the product; the results are interpreted by the selective excitation of the substrates.

Two-photon laser-induced reaction of 1,8-bis(halomethyl)naphthalenes from different excited states and transient targeting of its intermediate by time-delayed, two-color photolysis and argon ion laser-jet photolysis techniques

Two-photon chemistry of 1,8-bis(bromomethyl)naphthalene (1a) and 1,8-bis(chloromethyl)naphthalene (1b) was studied by (a) laser photolysis with use of XeCl (308 nm), KrF (248 nm), and ArF (193 nm) excimer lasers, (b) time-delayed, two-color photolysis with use of XeCl and XeF (351 nm) lasers, and (c) argon ion laser-jet (333, 351, and 364 nm) photolysis by both direct and benzophenone sensitization. The reaction proceeds through an intermediate monoradical 2, which is generated by a one-photon process, followed by additional photolysis to the two-photon product acenaphthene (4). On excitation of substrate 1 to its S1 state, monoradical 2 is formed directly from the S1 state and subsequently from the T1 state through intersystem crossing, alternatively on benzophenone sensitization. Upper excited states, namely S2 and S3, of 1 are proposed in the KrF and AsF excimer laser irradiation, generating intermediate 2 through fast fragmentation of the T(σ*) state. Transient targeting of intermediate 2 by time-delayed, two-color photolysis and argon ion laser-jet photolysis increases considerably the yield of the two-photon product 4.

Synthesis of Decorated Carbon Structures with Encapsulated Components by Low-Voltage Electric Discharge Treatment

Abstract: Polycondensation of complexes of chloromethanes with triphenylphosphine by the action of low-voltage electric discharges in the liquid phase gives nanosized solid products. The elemental composition involving the generation of element distribution maps (scanning electron microscopy–energy dispersive X?ray spectroscopy mapping) and the component composition (by direct evolved gas analysis–mass spectrometry) of the solid products have been studied. The elemental and component compositions of the result-ing structures vary widely depending on the chlorine content in the substrate and on the amount of triphenylphosphine taken. Thermal desorption analysis revealed abnormal behavior of HCl and benzene present in the solid products. In thermal desorption spectra, these components appear at an uncharacteristically high temperature. The observed anomaly in the behavior of HCl is due to HCl binding into a complex of the solid anion HCI-2 with triphenyl(chloromethyl)phosphonium chloride, which requires a relatively high temperature (up to 800 K) to decompose. The abnormal behavior of benzene is associated with its encapsulated state in nanostructures. The appearance of benzene begins at 650 K and continues up to temperatures above 1300?K.

Visible light enables catalytic formation of weak chemical bonds with molecular hydrogen

The synthesis of weak chemical bonds at or near thermodynamic potential is a fundamental challenge in chemistry, with applications ranging from catalysis to biology to energy science. Proton-coupled electron transfer using molecular hydrogen is an attractive strategy for synthesizing weak element–hydrogen bonds, but the intrinsic thermodynamics presents a challenge for reactivity. Here we describe the direct photocatalytic synthesis of extremely weak element–hydrogen bonds of metal amido and metal imido complexes, as well as organic compounds with bond dissociation free energies as low as 31 kcal mol?1. Key to this approach is the bifunctional behaviour of the chromophoric iridium hydride photocatalyst. Activation of molecular hydrogen occurs in the ground state and the resulting iridium hydride harvests visible light to enable spontaneous formation of weak chemical bonds near thermodynamic potential with no by-products. Photophysical and mechanistic studies corroborate radical-based reaction pathways and highlight the uniqueness of this photodriven approach in promoting new catalytic chemistry. [Figure not available: see fulltext.].

Proton donor effects on the reactivity of SmI2. Experimental and theoretical studies on methanol solvationvs. Aqueous solvation

Proton donors are important components of many reactions mediated by samarium diiodide (SmI2). The addition of water to SmI2creates a reagent system that enables the reduction of challenging substrates through proton-coupled electron-transfer (PCET). Simple alcohols such as methanol are often used successfully in reductions with SmI2but often have reduced reactivity. The basis for the change in reactivity of SmI2-H2O and SmI2-MeOH is not apparent given the modest differences between water and methanol. A combination of Born-Oppenheimer molecular dynamics simulations and mechanistic experiments were performed to examine the differences between the reductants formedin situfor the SmI2-H2O and SmI2-MeOH systems. This work demonstrates that reduced coordination of MeOH to Sm(ii) results in a complex that reduces arenes through a sequential electron proton transfer at low concentrations and that this process is significantly slower than reduction by SmI2-H2O.