Product Name

  • Name

    6-NITROCHRYSENE

  • EINECS
  • CAS No. 7496-02-8
  • Article Data15
  • CAS DataBase
  • Density 1.342g/cm3
  • Solubility
  • Melting Point 220 °C (dec.)(lit.)
  • Formula C18H11 N O2
  • Boiling Point 505°C at 760 mmHg
  • Molecular Weight 273.291
  • Flash Point 252.5°C
  • Transport Information
  • Appearance
  • Safety Confirmed carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also CHRYSENE and NITRO COMPOUNDS of AROMATIC HYDROCARBONS.
  • Risk Codes R45; R46; R20/21/22
  • Molecular Structure Molecular Structure of 7496-02-8 (6-NITROCHRYSENE)
  • Hazard Symbols 2134652
  • Synonyms 6-Nitrochrysene;NSC 407609
  • PSA 45.82000
  • LogP 5.57760

Synthetic route

chrysene
218-01-9

chrysene

6-nitrochrysene
7496-02-8

6-nitrochrysene

Conditions
ConditionsYield
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

chrysene

A

6-nitrochrysene
7496-02-8

6-nitrochrysene

B

6-nitrochrysene
7496-02-8

6-nitrochrysene

C

4-nitrochrysene

4-nitrochrysene

Conditions
ConditionsYield
With nitric acid In acetic anhydride at 20℃; for 120h; Yield given. Yields of byproduct given;
...Expand
chrysene
218-01-9

chrysene

nitric acid
7697-37-2

nitric acid

acetic acid
64-19-7

acetic acid

6-nitrochrysene
7496-02-8

6-nitrochrysene

Conditions
ConditionsYield
at 100℃;
at 100℃;
...Expand
chrysene
218-01-9

chrysene

sulfuric acid
7664-93-9

sulfuric acid

nitric acid
7697-37-2

nitric acid

acetic acid
64-19-7

acetic acid

6-nitrochrysene
7496-02-8

6-nitrochrysene

Conditions
ConditionsYield
at 40℃;
at 40℃;
...Expand
6-nitrochrysene
7496-02-8

6-nitrochrysene

6-aminochrysene
2642-98-0

6-aminochrysene

Conditions
ConditionsYield
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-nitrochrysene

6-hydroxylaminochrysene
114451-10-4

6-hydroxylaminochrysene

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrazine hydrate In tetrahydrofuran at -3℃; for 0.166667h; Inert atmosphere;80%
6-nitrochrysene
7496-02-8

6-nitrochrysene

acetic anhydride
108-24-7

acetic anhydride

6-acetoxychrysene
7499-59-4

6-acetoxychrysene

Conditions
ConditionsYield
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

6-nitrochrysene

12-nitro-chrysene-5,6-dione
32703-90-5

12-nitro-chrysene-5,6-dione

Conditions
ConditionsYield
With sodium dichromate; acetic acid
6-nitrochrysene
7496-02-8

6-nitrochrysene

6-chloro-12-nitro-chrysene

6-chloro-12-nitro-chrysene

Conditions
ConditionsYield
With sulfuryl dichloride; sodium acetate; nitrobenzene at 60℃;
6-nitrochrysene
7496-02-8

6-nitrochrysene

6-bromo-12-nitro-chrysene

6-bromo-12-nitro-chrysene

Conditions
ConditionsYield
With bromine; nitrobenzene at 60℃;
6-nitrochrysene
7496-02-8

6-nitrochrysene

hydrogen iodide
10034-85-2

hydrogen iodide

acetic acid
64-19-7

acetic acid

red phosphorus

red phosphorus

6-aminochrysene
2642-98-0

6-aminochrysene

...Expand
hydrogenchloride
7647-01-0

hydrogenchloride

6-nitrochrysene
7496-02-8

6-nitrochrysene

acetic acid
64-19-7

acetic acid

tin

tin

6-aminochrysene
2642-98-0

6-aminochrysene

Conditions
ConditionsYield
at 100℃;
...Expand
sulfuryl dichloride
7791-25-5

sulfuryl dichloride

6-nitrochrysene
7496-02-8

6-nitrochrysene

6-chloro-12-nitro-chrysene

6-chloro-12-nitro-chrysene

6-nitrochrysene
7496-02-8

6-nitrochrysene

bromine
7726-95-6

bromine

nitrobenzene
98-95-3

nitrobenzene

6-bromo-12-nitro-chrysene

6-bromo-12-nitro-chrysene

Conditions
ConditionsYield
at 60℃;
...Expand
6-nitrochrysene
7496-02-8

6-nitrochrysene

acetic acid
64-19-7

acetic acid

CrO3

CrO3

5-nitro-benzo[a]naphtho[2,1-c]phenazine
32703-91-6

5-nitro-benzo[a]naphtho[2,1-c]phenazine

Conditions
ConditionsYield
Umsetzung des Reaktionsprodukts mit o-Phenylendiamin;
...Expand
chrysene
218-01-9

chrysene

sulfuric acid
7664-93-9

sulfuric acid

6-nitrochrysene
7496-02-8

6-nitrochrysene

nitric acid
7697-37-2

nitric acid

acetic acid
64-19-7

acetic acid

6,12-dinitro-chrysene
7495-99-0

6,12-dinitro-chrysene

Conditions
ConditionsYield
at 45 - 50℃; zuletzt bei 100grad;
...Expand
6-nitrochrysene
7496-02-8

6-nitrochrysene

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

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
ConditionsYield
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

6-nitrochrysene

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

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
ConditionsYield
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

6-nitrochrysene

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

4-{4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-N-chrysen-6-yl-butyramide

Conditions
ConditionsYield
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

6-nitrochrysene

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

4-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-N-chrysen-6-yl-butyramide

Conditions
ConditionsYield
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

6-nitrochrysene

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

5-{5-Amino-4-[(S)-2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-pentanoic acid chrysen-6-ylamide

Conditions
ConditionsYield
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

6-nitrochrysene

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

5-{4-[(S)-2-(Bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-pentanoic acid chrysen-6-ylamide

Conditions
ConditionsYield
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

6-nitrochrysene

N-chrysen-6-yl-4-oxo-4-piperidin-1-yl-butyramide
219121-13-8

N-chrysen-6-yl-4-oxo-4-piperidin-1-yl-butyramide

Conditions
ConditionsYield
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

6-nitrochrysene

N-chrysen-6-yl-4-(4-methyl-piperazin-1-yl)-4-oxo-butyramide
219121-14-9

N-chrysen-6-yl-4-(4-methyl-piperazin-1-yl)-4-oxo-butyramide

Conditions
ConditionsYield
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

6-nitrochrysene

N-(6'-chryseneyl)-propane-3'-carboxy-1'-carboxamide
347142-85-2

N-(6'-chryseneyl)-propane-3'-carboxy-1'-carboxamide

Conditions
ConditionsYield
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

6-nitrochrysene

N-(6'-chryseneyl)-propane-1'-carboxamide-3'-ethylcarboxylate
28616-00-4

N-(6'-chryseneyl)-propane-1'-carboxamide-3'-ethylcarboxylate

Conditions
ConditionsYield
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

6-nitrochrysene

chrysen-6-yl-(4-morpholin-4-yl-butyl)-amine

chrysen-6-yl-(4-morpholin-4-yl-butyl)-amine

Conditions
ConditionsYield
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

6-nitrochrysene

N-chrysen-6-yl-3-oxo-3-piperidin-1-yl-propionamide

N-chrysen-6-yl-3-oxo-3-piperidin-1-yl-propionamide

Conditions
ConditionsYield
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

6-nitrochrysene

chrysen-6-yl-[4-(4-methyl-piperazin-1-yl)-butyl]-amine

chrysen-6-yl-[4-(4-methyl-piperazin-1-yl)-butyl]-amine

Conditions
ConditionsYield
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 Chemical Properties


IUPAC Name: 6-nitrochrysene 
Molecular Weight: 273.28544 g/mol
Molecular Formula: C18H11NO2
Density: 1.342 g/cm3
Melting Point: 220 °C (dec.)(lit.)
Boiling Point: 505 °C at 760 mmHg
Flash Point: 252.5 °C
Appreance: brown powder  
Molar Volume: 203.6 cm3
Polarizability: 34.22*10-24 cm3
Surface Tension: 63.2 dyne/cm 
Enthalpy of Vaporization: 74.53 kJ/mol
Vapour Pressure: 7.95E-10 mmHg at 25 °C 
XLogP3: 5.5
H-Bond Acceptor: 2
Exact Mass: 273.078979
MonoIsotopic Mass: 273.078979
Topological Polar Surface Area: 43.1
Heavy Atom Count: 21
Complexity: 405
Canonical SMILES: C1=CC=C2C(=C1)C=CC3=C2C=C(C4=CC=CC=C34)[N+](=O)[O-]
InChI: InChI=1S/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
InChIKey: UAWLTQJFZUYROA-UHFFFAOYSA-N
Storage temp.: 2-8 °C
Product Categories: Alphabetic; Environmental CRM; N;NA - NIApplication CRMs; Nitro-PAH; CarcinogensOrganic Building Blocks; Cancer Research; Nitro Compounds; Nitrogen Compounds

6-Nitrochrysene Toxicity Data With Reference

1.    

mmo-sat 5 µg/plate

     CNREA8    Cancer Research. 44 (1984),3408.
2.    

mma-sat 2500 ng/plate

     CNREA8    Cancer Research. 44 (1984),3408.
3.    

otr-ham:emb 3700 nmol/L

     CRNGDP    Carcinogenesis. 4 (1983),357.

6-Nitrochrysene Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 46 ,1989,p. 267.(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 . 46 ,1989,p. 267.(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) ; Human No Adequate Data IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 46 ,1989,p. 267.(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) .

6-Nitrochrysene Safety Profile

Confirmed carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also CHRYSENE and NITRO COMPOUNDS of AROMATIC HYDROCARBONS.
 

Hazard Codes: ToxicT
Risk Statements: 45-46-20/21/22
R45: May cause cancer
R46: May cause heritable genetic damage
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 53-22-36/37/39-45
S53: Avoid exposure - obtain special instructions before use
S22: Do not breathe dust
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible)
WGK Germany: 3
RTECS: GC1930000

6-Nitrochrysene Specification

 6-Nitrochrysene (CAS NO.7496-02-8) is also called 84218, 6-Nitrochrysene (purity) ; 6-Nitrochrysene, 99% . 6-Nitrochrysene (CAS NO.7496-02-8) is chrome-red thick prismatic crystal or orange-yellow needle (recrystallized from pyridine or xylene). 6-Nitrochrysene (CAS NO.7496-02-8)  reacts with tin and hydrochloric acid in glacial acetic acid. It also reacts with bromine and fuming nitric acid. When heated to decomposition 6-Nitrochrysene (CAS NO.7496-02-8) emits toxic fumes of nitrogen oxides. Flash point data for 6-Nitrochrysene (CAS NO.7496-02-8) are not available; however, It is probably combustible.

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