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Acenaphthalene

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Name

Acenaphthalene

EINECS 205-917-1
CAS No. 208-96-8 Density 1.187 g/cm3
PSA 0.00000 LogP 3.32360
Solubility N/A Melting Point 78-82 °C
Formula C12H8 Boiling Point 298.86 °C at 760 mmHg
Molecular Weight 152.196 Flash Point 137.161 °C
Transport Information UN 1145 3/PG 2 Appearance yellow crystalline powder
Safety 26-36/37/39-62-61-60-45-36/37-16-7-37/39 Risk Codes 22-36/37/38-67-65-50/53-38-11-39/23/24/25-23/24/25
Molecular Structure Molecular Structure of 208-96-8 (Acenaphthalene) Hazard Symbols HarmfulXn; DangerousN; ToxicT; IrritantXi; FlammableF
Synonyms

Cyclopenta[de]naphthalene;NSC 59821;Acenaphthalene;

Article Data 147

Acenaphthalene Synthetic route

51392-61-1

1-bromo-1H,3H-naphtho<1,8-cd>thiopyran 2,2-dioxide

208-96-8

acenaphthylene

Conditions
ConditionsYield
With sodium methylate In methanol for 16.5h; Ambient temperature;97%
With sodium methylate In methanol for 16.5h; Product distribution; Ambient temperature; var. of base;97%
83-32-9

acenaphthene

1518-16-7

7,7',8,8'-tetracyanoquinodimethane

A

77074-97-6

9-Acenaphthyl<4-(dicyanomethyl)phenyl>dicyanomethane

B

208-96-8

acenaphthylene

Conditions
ConditionsYield
for 0.0833333h; Heating;A 95.5%
B n/a
164665-41-2

Carbonic acid acenaphthen-1-yl ester methyl ester

208-96-8

acenaphthylene

Conditions
ConditionsYield
With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 60℃; for 48h;95%
182313-38-8

Propynoic acid acenaphthen-1-yl ester

208-96-8

acenaphthylene

Conditions
ConditionsYield
at 760℃; under 0.03 Torr;95%
Multi-step reaction with 2 steps
1: 32 percent / deuterium oxide, triethylamine / tetrahydrofuran / 1.25 h / 35 °C
2: 95 percent / 760 °C / 0.03 Torr
View Scheme

1,2-dihydroacenaphthylen-1-yl (3-(2)H)propyonate

208-96-8

acenaphthylene

Conditions
ConditionsYield
at 760℃; under 0.03 Torr;95%
25226-58-8

trans-1,2-dibromo-1,2-dihydroacenaphthylene

208-96-8

acenaphthylene

Conditions
ConditionsYield
With acetic acid; zinc94%
With ethanol; zinc
14209-08-6

1,2-dibromoacenaphthene

208-96-8

acenaphthylene

Conditions
ConditionsYield
With sodium sulfide; Aliquat 336 In water; benzene for 1h; Ambient temperature;92%
6306-07-6

1-acenaphthenol

208-96-8

acenaphthylene

Conditions
ConditionsYield
methyltrioxorhenium(VII) In benzene for 72h;89%
zirconium(IV) chloride In acetonitrile at 20℃; for 0.666667h;89%
With pyridine; thionyl chloride

C27H20N2O2

A

103-30-0

(E)-1,2-diphenyl-ethene

B

208-96-8

acenaphthylene

Conditions
ConditionsYield
at 500℃; under 0.02 Torr; for 0.0833333h;A 88%
B 4%

2-[2-(1-chloro-vinyl)-phenyl]-thiophene

A

234-41-3

naphtho[1,2-b]thiophene

B

208-96-8

acenaphthylene

Conditions
ConditionsYield
at 800℃; under 0.1 Torr; Cyclization; Pyrolysis;A 81%
B 2%

Acenaphthalene Consensus Reports

Reported in EPA TSCA Inventory.

Acenaphthalene Analytical Methods

For occupational chemical analysis use NIOSH: Polynuclear Aromatic Hydrocarbons (HPLC), 5506; (GC), 5515.

Acenaphthalene Specification

1. Introduction of Acenaphthalene

The IUPAC name of this chemical is Acenaphthylene. With the CAS registry number 208-96-8 and EINECS 205-917-1, it is also named as Cyclopenta(de)naphthalene. In addition, the molecular formula is C12H8 and the molecular weight is 152.20. It is a kind of yellow crystalline powder and insoluble in water. What's more, it belongs to the class of Industrial/Fine Chemicals; AA to ALAnalytical Standards; A; A-BAlphabetic; Alpha Sort; AromaticsChemical Class; Chemical Class; Hydrocarbons; NeatsAnalytical Standards; PAHs; Volatiles/ Semivolatiles; Arenes; Building Blocks; Organic Building Blocks; Naphthalenes; AA to AL; Alphabetic.

2. Physical properties about this chemical

(1)ACD/LogP: 3.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.266; (4)ACD/LogD (pH 7.4): 3.266; (5)ACD/BCF (pH 5.5): 178.758; (6)ACD/BCF (pH 7.4): 178.758; (7)ACD/KOC (pH 5.5): 1424.886; (8)ACD/KOC (pH 7.4): 1424.886; (9)Index of Refraction: 1.732; (10)Molar Refractivity: 51.262 cm3; (11)Molar Volume: 128.196 cm3; (12)Polarizability: 20.322 ×10-24cm3; (13)Surface Tension: 54.72 dyne/cm; (14)Density: 1.187 g/cm3; (15)Flash Point: 137.161 °C; (16)Enthalpy of Vaporization: 51.726 kJ/mol; (17)Boiling Point: 298.86 °C at 760 mmHg; (18)Vapour Pressure: 0.002 mmHg at 25°C.

3.Structure descriptors of Acenaphthalene

(1)SMILES: c1cc2cccc3c2c(c1)C=C3
(2)InChI: InChI=1/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H
(3)InChIKey: HXGDTGSAIMULJN-UHFFFAOYAQ

4. Preparation of Acenaphthylene

Acenaphthalene can be prepared by acenaphthene through vapor-phase catalytic dehydrogenation. Put industrial acenaphthene into molten kettle, use an indirect steam heat it to melt, then use compressed air press acenaphthene liquid into the spiral mixer gasification. After heating the mixture to about 450 °C, let the mixture into dehydrogenation reactor for catalytic dehydrogenation, condense and dry the product.

5.Uses of Acenaphthylene

Acenaphthalene can be used for determinating aryl aldehyde. And it can be used to get 1,2-dichloro-acenaphthene. This reaction will need reagents iodosobenzene and HCl-silica gel and solvent solid. The reaction time is 5 minutes at ambient temperature. The yield is about 31%.

Acenaphthylene can be used to get 1,2-dichloro-acenaphthene

6.Safety information of Acenaphthalene

This chemical is highly flammable, harmful if swallowed and irritating to eyes, respiratory system and skin. It may cause lung damage if swallowed and may cause drowsiness and dizziness. In addition, it is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. And it has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. During using it,  avoid release to the environment and wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). This material and its container must be disposed of as hazardous waste. And you should refer to special instructions/safety data sheets. If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. Keep away from sources of ignition and keep container tightly closed at last.

7.The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 1760mg/kg (1760mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BLOOD: HEMORRHAGE
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 9(9), Pg. 53, 1965.
rat LD50 intraperitoneal 1700mg/kg (1700mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 14(6), Pg. 46, 1970.

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