7496-02-8

Basic information

• Product Name: 6-NITROCHRYSENE
• Synonyms: 6-NITROCHRYSENE;84218, 6-Nitrochrysene (purity);6-Nitrochrysene,99%
• CAS NO: 7496-02-8
• Molecular Formula: C₁₈H₁₁NO₂
• Molecular Weight: 273.29
• Product Categories: Alphabetic;Environmental CRM;N;NA - NIApplication CRMs;Nitro-PAH;CarcinogensOrganic Building Blocks;Cancer Research;Nitro Compounds;Nitrogen Compounds
• Mol File: 7496-02-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 220 °C (dec.)(lit.)
• Boiling Point: 416.31°C (rough estimate)
• Flash Point: 252.5°C
• Appearance: /
• Density: 1.2123 (rough estimate)
• Vapor Pressure: 7.95E-10mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly, Sonicated)
• BRN: 2134652
• CAS DataBase Reference: 6-NITROCHRYSENE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-NITROCHRYSENE(7496-02-8)
• EPA Substance Registry System: 6-NITROCHRYSENE(7496-02-8)

Safety Data

• Hazard Codes: T
• Statements: 45-46-20/21/22
• Safety Statements: 53-22-36/37/39-45
• WGK Germany: 3
• RTECS: GC1930000
• Hazardous Substances Data: 7496-02-8(Hazardous Substances Data)

Usage

Chemical Properties

brown powder

Uses

Different sources of media describe the Uses of 7496-02-8 differently. You can refer to the following data:
1. There is no evidence that 6-nitrochrysene has been used commercially for any purpose. 6-Nitrochrysene is used as an internal standard in the chemical analysis of nitroarenes (IARC 1989). It is available for research purposes at a purity of at least 98% and as a reference material at a certified purity of 98.9%.
2. 6-Nitrochrysene is a nitro-polycyclic aromatic hydrocarbon and a carcinogen selector. An environmental contaminant and a carcinogen.

General Description

Chrome-red thick prismatic crystals or orange-yellow needles (recrystallized from pyridine or xylene).

Reactivity Profile

6-NITROCHRYSENE reacts with tin and hydrochloric acid in glacial acetic acid. 6-NITROCHRYSENE also reacts with bromine and fuming nitric acid.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 6-NITROCHRYSENE emits toxic fumes of nitrogen oxides.

Fire Hazard

Flash point data for 6-NITROCHRYSENE are not available; however, 6-NITROCHRYSENE is probably combustible.

Carcinogenicity

6-Nitrochrysene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

InChI:InChI=1/C18H11NO2/c20-19(21)18-11-17-13-6-2-1-5-12(13)9-10-15(17)14-7-3-4-8-16(14)18/h1-11H

Synthetic route

chrysene (218-01-9) → 6-nitrochrysene (7496-02-8)

Conditions	Yield
With bismuth(III) nitrate; Montmorillonite KSF for 0.25h; Nitration;	92%
With sulfuric acid; nitric acid; silica gel In dichloromethane at 25℃; for 24h; Nitration;	82%
With methanesulfonic acid; dinitrogen tetraoxide In dichloromethane at 20℃; for 0.25h; Product distribution; Rate constant; various additivities, nitration of polycyclic aromatic hydrocarbons by N2O4, selectivity, relative reactivities, effect of acid, base; synthetic and mechanistic study;

chrysene (218-01-9) → 6-nitrochrysene (7496-02-8) + 6-nitrochrysene (7496-02-8) + 4-nitrochrysene

Conditions	Yield
With nitric acid In acetic anhydride at 20℃; for 120h; Yield given. Yields of byproduct given;

chrysene (218-01-9) + nitric acid (7697-37-2) + acetic acid (64-19-7) → 6-nitrochrysene (7496-02-8)

Conditions	Yield
at 100℃;
at 100℃;

chrysene (218-01-9) + sulfuric acid (7664-93-9) + nitric acid (7697-37-2) + acetic acid (64-19-7) → 6-nitrochrysene (7496-02-8)

Conditions	Yield
at 40℃;
at 40℃;

6-nitrochrysene (7496-02-8) → 6-aminochrysene (2642-98-0)

Conditions	Yield
With ammonium acetate; zinc In water Product distribution; Ambient temperature; influence of ammonium acetate; the lenght of the reducer column;;	99%
With samarium; iodine In methanol for 8h; Heating;	94%
With samarium; iodine In methanol for 8h; Heating;	90%

6-nitrochrysene (7496-02-8) → 6-hydroxylaminochrysene (114451-10-4)

Conditions	Yield
With 5%-palladium/activated carbon; hydrazine hydrate In tetrahydrofuran at -3℃; for 0.166667h; Inert atmosphere;	80%

6-nitrochrysene (7496-02-8) + acetic anhydride (108-24-7) → 6-acetoxychrysene (7499-59-4)

Conditions	Yield
Stage #1: 6-nitrochrysene With perhydrodibenzo-18-crown-6 In N,N-dimethyl-formamide at 20℃; for 4h; Oxidation; Stage #2: acetic anhydride With pyridine Acetylation;	65%

6-nitrochrysene (7496-02-8) → 12-nitro-chrysene-5,6-dione (32703-90-5)

Conditions	Yield
With sodium dichromate; acetic acid

6-nitrochrysene (7496-02-8) → 6-chloro-12-nitro-chrysene

Conditions	Yield
With sulfuryl dichloride; sodium acetate; nitrobenzene at 60℃;

6-nitrochrysene (7496-02-8) → 6-bromo-12-nitro-chrysene

Conditions	Yield
With bromine; nitrobenzene at 60℃;

6-nitrochrysene (7496-02-8) + hydrogen iodide (10034-85-2) + acetic acid (64-19-7) + red phosphorus → 6-aminochrysene (2642-98-0)

hydrogenchloride (7647-01-0) + 6-nitrochrysene (7496-02-8) + acetic acid (64-19-7) + tin → 6-aminochrysene (2642-98-0)

Conditions	Yield
at 100℃;

sulfuryl dichloride (7791-25-5) + 6-nitrochrysene (7496-02-8) → 6-chloro-12-nitro-chrysene

6-nitrochrysene (7496-02-8) + bromine (7726-95-6) + nitrobenzene (98-95-3) → 6-bromo-12-nitro-chrysene

Conditions	Yield
at 60℃;

6-nitrochrysene (7496-02-8) + acetic acid (64-19-7) + CrO3 → 5-nitro-benzo[a]naphtho[2,1-c]phenazine (32703-91-6)

Conditions	Yield
Umsetzung des Reaktionsprodukts mit o-Phenylendiamin;

chrysene (218-01-9) + sulfuric acid (7664-93-9) + 6-nitrochrysene (7496-02-8) + nitric acid (7697-37-2) + acetic acid (64-19-7) → 6,12-dinitro-chrysene (7495-99-0)

Conditions	Yield
at 45 - 50℃; zuletzt bei 100grad;

6-nitrochrysene (7496-02-8) → N-chrysen-6-yl-4-(7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)-butyramide

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / SnCl2*2H2O / ethyl acetate / 3 h 2: isobutyl chloroformate; triethylamine / 12 h / 20 °C 3: 72 percent / SnCl2*2H2O / ethyl acetate / 3 h / Heating 4: HgCl2; CaCO3 / acetonitrile; H2O / 12 h / 20 °C View Scheme

6-nitrochrysene (7496-02-8) → 5-(7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)-pentanoic acid chrysen-6-ylamide

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / SnCl2*2H2O / ethyl acetate / 3 h 2: isobutyl chloroformate; triethylamine / 12 h / 20 °C 3: 72 percent / SnCl2*2H2O / ethyl acetate / 3 h / Heating 4: HgCl2; CaCO3 / acetonitrile; H2O / 12 h / 20 °C View Scheme

6-nitrochrysene (7496-02-8) → 4-{4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-N-chrysen-6-yl-butyramide (625457-62-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / SnCl2*2H2O / ethyl acetate / 3 h 2: isobutyl chloroformate; triethylamine / 12 h / 20 °C View Scheme

6-nitrochrysene (7496-02-8) → 4-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-N-chrysen-6-yl-butyramide (625457-64-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / SnCl2*2H2O / ethyl acetate / 3 h 2: isobutyl chloroformate; triethylamine / 12 h / 20 °C 3: 72 percent / SnCl2*2H2O / ethyl acetate / 3 h / Heating View Scheme

6-nitrochrysene (7496-02-8) → 5-{5-Amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid chrysen-6-ylamide (625457-65-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / SnCl2*2H2O / ethyl acetate / 3 h 2: isobutyl chloroformate; triethylamine / 12 h / 20 °C 3: 72 percent / SnCl2*2H2O / ethyl acetate / 3 h / Heating View Scheme

6-nitrochrysene (7496-02-8) → 5-{4-[(S)-2-(Bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentanoic acid chrysen-6-ylamide (625457-63-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / SnCl2*2H2O / ethyl acetate / 3 h 2: isobutyl chloroformate; triethylamine / 12 h / 20 °C View Scheme

6-nitrochrysene (7496-02-8) → N-chrysen-6-yl-4-oxo-4-piperidin-1-yl-butyramide (219121-13-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Sm; I2 / methanol / 8 h / Heating 2: isobutylchloroformate; TEA / CH2Cl2 / 20 °C View Scheme

6-nitrochrysene (7496-02-8) → N-chrysen-6-yl-4-(4-methyl-piperazin-1-yl)-4-oxo-butyramide (219121-14-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Sm; I2 / methanol / 8 h / Heating 2: isobutylchloroformate; TEA / CH2Cl2 / 20 °C View Scheme

6-nitrochrysene (7496-02-8) → N-(6'-chryseneyl)-propane-3'-carboxy-1'-carboxamide (347142-85-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / Sm; I2 / methanol / 8 h / Heating 2: 90 percent / TEA / CH2Cl2 / 4 h / 20 °C 3: 90 percent / NaOH / methanol / 3 h / 20 °C View Scheme

6-nitrochrysene (7496-02-8) → N-(6'-chryseneyl)-propane-1'-carboxamide-3'-ethylcarboxylate (28616-00-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Sm; I2 / methanol / 8 h / Heating 2: 90 percent / TEA / CH2Cl2 / 4 h / 20 °C View Scheme

6-nitrochrysene (7496-02-8) → chrysen-6-yl-(4-morpholin-4-yl-butyl)-amine

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / Sm; I2 / methanol / 8 h / Heating 2: isobutylchloroformate; TEA / CH2Cl2 / 20 °C 3: 80 percent / LiAlH4 / tetrahydrofuran / 12 h / Heating View Scheme

6-nitrochrysene (7496-02-8) → N-chrysen-6-yl-3-oxo-3-piperidin-1-yl-propionamide

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / Sm; I2 / methanol / 8 h / Heating 2: 90 percent / TEA / CH2Cl2 / 4 h / 20 °C 3: 90 percent / NaOH / methanol / 3 h / 20 °C 4: HOBT; BOP; N-methylmorpholine / dimethylformamide / 20 °C View Scheme

6-nitrochrysene (7496-02-8) → chrysen-6-yl-[4-(4-methyl-piperazin-1-yl)-butyl]-amine

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / Sm; I2 / methanol / 8 h / Heating 2: isobutylchloroformate; TEA / CH2Cl2 / 20 °C 3: 80 percent / LiAlH4 / tetrahydrofuran / 12 h / Heating View Scheme

Upstream product

• 218-01-9 chrysene 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 

Downstream Products

• 2642-98-0 6-aminochrysene 
• 7495-99-0 6,12-dinitro-chrysene 
• 7499-59-4 6-acetoxychrysene 
• 114451-10-4 6-hydroxylaminochrysene 
• 37515-51-8 6-hydroxychrysene 

Relevant articles and documents

Microwave-induced surface-mediated highly efficient regioselective nitration of aromatic compounds: Effects of penetration depth

Surface mediated highly regioselective nitration of aromatic compounds under diverse microwave-induced conditions was investigated in this work. The effects of the penetration depth of the surfaces were found to be more crucial than other dielectric parameters. Despite significant progress of microwave-induced reactions, no reports have examined the penetration depth of the surfaces used in these processes.

Surface-mediated highly efficient regioselective nitration of aromatic compounds by bismuth nitrate

Montmorillonite impregnated with bismuth nitrate was found to be an excellent reagent for aromatic nitration in high yield. (C) 2000 Elsevier Science Ltd.

Nitration of Polycyclic Aromatic Hydrocarbons by Dinitrogen Tetraoxide. II. Synthetic and Mechanistic Aspects

Treatment of polycyclic aromatic hydrocarbons by dinitrogen tetraoxide in dichloromethane solution leads to the clean production of mononitro derivatives with high positional selectivity in almost quantitative yields.For substrates less reactive than chrysene the addition of catalytic amounts of acid is required for the reaction to proceed at convenient rates.Being very easily performed, the method should be regarded as the best yet found for the synthesis of small amount of these, in many cases, mutagenic mononitro compounds.From studies on relative reactivities, isomer distributions, and the effect of acid, base and nitrosonium ion on the reaction, a mechanism involving initial attack of a novel electrophile, nitrosated dinitrogen tetraoxide, is proposed.The initially formed ?-complex is suggested to be transformed into the nitro ?-complex via a pathway involving radical pairs, thus explaining the observation by others of CIDNP effects on the reaction path of nitrous acid catalyzed nitration, a reaction proposed to follow the same reaction scheme.