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602-87-9

Basic Information
CAS No.: 602-87-9
Name: 5-NITROACENAPHTHENE
Article Data: 51
Molecular Structure:
Molecular Structure of 602-87-9 (5-NITROACENAPHTHENE)
Formula: C12H9NO2
Molecular Weight: 199.209
Synonyms: Acenaphthene,5-nitro- (6CI,7CI,8CI);5-Nitroacenaphthene;NSC 1312;NSC 22421;
EINECS: 210-025-0
Density: 1.357 g/cm3
Melting Point: 100-101 °C
Boiling Point: 377.5 °C at 760 mmHg
Flash Point: 191.8 °C
Solubility: Insoluble in water
Appearance: yellow powder
Hazard Symbols: ToxicT, IrritantXi
Risk Codes: 45
Safety: 53-45
Transport Information: 2811
PSA: 45.82000
LogP: 3.36980
Synthetic route
83-32-9

acenaphthene

602-87-9

4-nitroacenaphthene

Conditions
ConditionsYield
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%
61631-80-9

6-nitro-acenaphthen-5-ylamine

602-87-9

4-nitroacenaphthene

Conditions
ConditionsYield
(i) aq. HCl, NaNO2, (ii) Cu2O, aq. NH3; Multistep reaction;
83-32-9

acenaphthene

A

3807-77-0

3-nitroacenaphthene

B

602-87-9

4-nitroacenaphthene

Conditions
ConditionsYield
With nitric acid; perfluoro-o-phenylenemercury trimer; sodium chloride; sodium nitrite In nitrobenzene; benzene at 21℃; for 0.666667h; Product distribution; various reaction conditions;
With Hg5(C(CF3)2)5; cis-nitrous acid; sodium chloride In nitrobenzene; benzene at 21℃; Yield given. Yields of byproduct given;
With nitric acid In acetic anhydride for 3h; Overall yield = 98 %; Overall yield = 0.78 g;
60-29-7

diethyl ether

83-32-9

acenaphthene

NO2

NO2

602-87-9

4-nitroacenaphthene

Conditions
ConditionsYield
at 15℃;
83-32-9

acenaphthene

64-19-7

acetic acid

NO2

NO2

602-87-9

4-nitroacenaphthene

Conditions
ConditionsYield
at 20 - 25℃;
83-32-9

acenaphthene

71-43-2

benzene

NO2

NO2

602-87-9

4-nitroacenaphthene

Conditions
ConditionsYield
at 20 - 25℃;
83-32-9

acenaphthene

benzoyl nitrate

benzoyl nitrate

petroleum ether

petroleum ether

A

3807-77-0

3-nitroacenaphthene

B

602-87-9

4-nitroacenaphthene

Conditions
ConditionsYield
at -10℃;
7697-37-2

nitric acid

108-24-7

acetic anhydride

83-32-9

acenaphthene

A

3807-77-0

3-nitroacenaphthene

B

602-87-9

4-nitroacenaphthene

C

1015-74-3

4-nitro-acenaphthene

7697-37-2

nitric acid

83-32-9

acenaphthene

64-19-7

acetic acid

A

602-87-9

4-nitroacenaphthene

B

x.x-dinitro-acenaphthene

x.x-dinitro-acenaphthene

83-32-9

acenaphthene

benzoyl nitrate

benzoyl nitrate

602-87-9

4-nitroacenaphthene

Conditions
ConditionsYield
With Petroleum ether at -10℃;
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  • 1,2-dihydro-5-nitroacenaphthylene

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    602-87-9

    1,2-dihydro-5-nitroacenaphthylene

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Consensus Reports

IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of chemicals to Man . 16 ,1978,p. 319.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-118 ,1978. . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Standards and Recommendations

DFG MAK: Animal Carcinogen, Suspected Human Carcinogen

Specification

The IUPAC name of 5-Nitroacenaphthene is 5-nitro-1,2-dihydroacenaphthylene. With the CAS registry number 602-87-9, it is also named as 1,2-Dihydro-5-nitro-acenaphthylene. The product's categories are Intermediates of Dyes and Pigments; Aromatic Compounds. It is yellow powder which is soluble in water, ethanol, ether and petroleum ether. This chemical is also stable, combustible and incompatible with strong oxidizing agents. Additionally, it should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.92; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.92; (4)ACD/LogD (pH 7.4): 3.92; (5)ACD/BCF (pH 5.5): 558.93; (6)ACD/BCF (pH 7.4): 558.93; (7)ACD/KOC (pH 5.5): 3222.28; (8)ACD/KOC (pH 7.4): 3222.28; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.723; (13)Molar Refractivity: 58.2 cm3; (14)Molar Volume: 146.7 cm3; (15)Polarizability: 23.07×10-24 cm3; (16)Surface Tension: 62.6 dyne/cm; (17)Enthalpy of Vaporization: 60.07 kJ/mol; (18)Vapour Pressure: 1.46E-05 mmHg at 25°C; (19)Exact Mass: 199.063329; (20)MonoIsotopic Mass: 199.063329; (21)Topological Polar Surface Area: 45.8; (22)Heavy Atom Count: 15; (23)Complexity: 273.

Preparation of 5-Nitroacenaphthene: It can be derived from nitration of acenaphthene. Adding glacial acetic acid into the dry glass-lined reactor and adding industrial acenaphthene (melting point: 92-94 °C) with the stirring. Stirring 10min at 70 °C. Then cooling to 23 °C. Adding 65% nitric acid dropwise at the temperature of 23-26 °C and stirring 1h at 23-26 °C. At last, we can get the product.

Uses of 5-Nitroacenaphthene: It is used as intermediate of dyes. And it is also used as chemical reagent. In addition, it can react with methylmagnesium chloride to get 5-chloro-4-methyl-acenaphthene. This reaction needs reagent sodium hypochlorite, potassium hydroxide and solvent tetrahydrofuran, H2O, ethanol at ambient temperature. The reaction time is 10 min. The yield is 89%.

When you are using this chemical, please be cautious about it as the following:
It may cause cancer. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) And avoid exposure - obtain special instructions before use.

People can use the following data to convert to the molecule structure.
1. SMILES:[O-][N+](=O)c1ccc3c2c1cccc2CC3
2. InChI:InChI=1/C12H9NO2/c14-13(15)11-7-6-9-5-4-8-2-1-3-10(11)12(8)9/h1-3,6-7H,4-5H2 
3. InChIKey:CUARLQDWYSRQDF-UHFFFAOYAL