7496-02-8

Usage

Uses

Used in Chemical Analysis:
6-Nitrochrysene is used as an internal standard in the chemical analysis of nitroarenes, which aids in the accurate determination of these compounds in various samples. 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%.
Used in Environmental and Health Research:
As a carcinogen selector and an environmental contaminant, 6-Nitrochrysene plays a role in research related to understanding the effects of nitro-polycyclic aromatic hydrocarbons on human health and the environment. This knowledge is crucial for developing strategies to mitigate the risks associated with exposure to these harmful substances.

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

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

Relevant academic research and scientific papers

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.

Chrysene-Based Azahelicene π-Linker of D-π-D-Type Hole-Transporting Materials for Perovskite Solar Cells

Chrysene is a readily available material for exploring new polycyclic aromatic hydrocarbons (PAHs). In this study, two chrysene based azahelicenes, nine-membered BA7 and ten-membered DA6, are constructed by intermolecular oxidative annulation of 6-aminochrysene and intramolecular annulation of N6,N12-bis(1-chloronaphthalen-2-yl)chrysene-6,12-diamine, respectively. The hexylated BA7 and DA6 and their brominated products were undoubtedly characterized by single crystal XRD. Subsequent amination with bis(9-methyl-9H-carbazol-3-yl)amine (BMCA) electron donor afforded D-π-D-type semiconductors BA7-BMCA and DA6-BMCA with beneficial properties to act as hole transport materials for perovskite solar cell. Compared with 19.4 % champion power conversion efficiency (PCE) of BA7-BMCA based device, a higher PCE of 20.2 % for DA6-BMCA counterpart may be attributed to its S-shaped double helicene-like linker with extended π-conjugated system.

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 using a supported catalyst

We report the use of a catalyst, sulfuric acid supported on silica-gel, as a promising method for facile, high yielding, regioselective syntheses of mononitrated polycyclic aromatic hydrocarbons, 6-nitrochrysene, 1- nitropyrene, 1-nitronaphthalene, 2-nitrofluorene, 3-nitrofluoranthene, and 9- nitroanthracene.

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.

Separation and Characterization of Mononitro Derivatives of Phenanthrene, Pyrene, Chrysene, Fluoranthene and Triphenylene

Mononitro derivatives of selected polycyclic aromatic hydrocarbons with 3 and 4 condensed rings have been synthesized to obtain samples for measurements of mutagenic properties.Crude purification of the compounds was carried out on gravity columns prior to final purification by HPLC to a purity of approximately 99.9percent.Structural isomers were identified from NMR, MS and UV spectra.