benzopyrene
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In 1,2-dichloro-ethane at 25℃; for 2h; Inert atmosphere; Schlenk technique; | 90% |
With methanesulfonic acid In dichloromethane at 0℃; | 57% |
5-ethynylchrysene
benzopyrene
Conditions | Yield |
---|---|
With platinum(II) chloride In toluene at 80℃; | 65% |
9,10-dihydro benzopyrene
benzopyrene
Conditions | Yield |
---|---|
palladium on activated charcoal at 300 - 305℃; | 60% |
With KO2; 18-crown-6 ether In N,N-dimethyl-formamide for 20h; Ambient temperature; | 86 % Chromat. |
cis-4,5-Diacetoxy-4,5-dihydrobenzopyrene
A
benzopyrene
B
4-Acetoxybenzopyrene
C
5-Acetoxybenzopyrene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 4h; Heating; | A n/a B 30% C 11% |
1,8-bis(ethynyl)naphthalene
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
benzopyrene
Conditions | Yield |
---|---|
With fluoride In tetrahydrofuran Ambient temperature; | 30% |
Conditions | Yield |
---|---|
With Tetramethylammonium dihydrogen trifluoride In acetonitrile for 1h; | A n/a B 25% |
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane Heating; | 23% |
Conditions | Yield |
---|---|
With Tetramethylammonium dihydrogen trifluoride In acetonitrile for 1h; | A n/a B 20% |
4,5-dihydro(epoxy) benzopyrene
benzopyrene
Conditions | Yield |
---|---|
With tetraphenylporphinatoiron(II)(pyridine)2 for 60h; Ambient temperature; | 8% |
1,6,10b,11,12,12a-hexahydro-2H-benzo[def]chrysen-3-one
benzopyrene
Conditions | Yield |
---|---|
With potassium hydroxide; hydrazine hydrate; diethylene glycol Erhitzen des Reaktionsprodukts an Palladium auf 300-320grad; |
Conditions | Yield |
---|---|
With palladium on activated charcoal at 310 - 320℃; | |
Multi-step reaction with 2 steps 1: 93 percent / glacial acetic acid, conc. HCl / 0.25 h 2: 60 percent / 10percent palladium on charcoal / 300 - 305 °C View Scheme |
2'-ethyl-3,4,5,6,7,8-hexahydro-1H-spiro[anthracene-2,1'-cyclopentane]
benzopyrene
Conditions | Yield |
---|---|
With platinum on activated charcoal at 350℃; |
5-hydroxy-3-oxo-2,3,11,12-tetrahydro-1H-benzo[def]chrysene-12a-carboxylic acid methyl ester
benzopyrene
Conditions | Yield |
---|---|
With zinc |
7,8,9,10-tetrahydrobenzo[a]pyrene
A
benzopyrene
B
7,8-dihydrobenzopyrene
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 5h; Ambient temperature; Title compound not separated from byproducts; | A 19 % Chromat. B 66 % Chromat. |
11,12-dihydrobenzopyrene
benzopyrene
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 2h; Heating; Yield given; |
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; aluminium trichloride 1.) carbon disulfide, reflux, 1 h; 2.) toluene, reflux; Yield given. Multistep reaction; |
A
benzo[a]pyrene-6,12-dione
B
benzopyrene
C
benzo[a]pyrene-1,6-quinone
D
benzo[a]pyrene-3,6-dione
Conditions | Yield |
---|---|
With water for 0.25h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
9,10-dihydro benzopyrene
A
benzopyrene
B
(7R,8S)-7,8-epoxy-7,8,9,10-tetrahydrobenzopyrene
C
(7S,8R)-7,8-epoxy-7,8,9,10-tetrahydrobenzopyrene
Conditions | Yield |
---|---|
With sodium hypochlorite; tetralin; Jacobsen's catalyst In dichloromethane at 0℃; for 2.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With quinoline; sodium methylate 1.) RT, 3 h, 2.) 180 deg C, 16 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
In various solvent(s) at 399.85℃; Condensation; Formation of xenobiotics; |
benzopyrene
Conditions | Yield |
---|---|
combustion; Formation of xenobiotics; |
benzopyrene
Conditions | Yield |
---|---|
combustion; Formation of xenobiotics; |
benzopyrene
Conditions | Yield |
---|---|
With air Oxidation; Formation of xenobiotics; |
A
2,2'-binaphthalene
B
Benzo[k]fluoranthene
C
benzopyrene
D
1-phenyl phenanthrene
Conditions | Yield |
---|---|
With air at 600 - 900℃; Oxidation; Formation of xenobiotics; Further byproducts given; |
Conditions | Yield |
---|---|
With air at 850 - 950℃; Oxidation; Formation of xenobiotics; |
A
9H-fluorene
B
phenanthrene
C
benzopyrene
D
cyclopenta[c,d]pyrene
Conditions | Yield |
---|---|
With air at 1496.85℃; Oxidation; Formation of xenobiotics; |
A
Indeno[1,2,3-cd]pyrene
B
benzopyrene
C
dibenzo[a,h]anthracene
D
Benzo[ghi]perylene
Conditions | Yield |
---|---|
With air Oxidation; Formation of xenobiotics; Further byproducts given; |
Conditions | Yield |
---|---|
at 70℃; |
benzopyrene
Conditions | Yield |
---|---|
With palladium on activated charcoal at 300 - 320℃; |
benzopyrene
4,5-dihydrobenzopyrene
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethyl acetate under 1034.3 Torr; for 24h; Product distribution; Ambient temperature; | 100% |
With hydrogen; palladium on activated charcoal In ethyl acetate under 1034.3 Torr; for 24h; Ambient temperature; | 100% |
With hydrogen; Pd/SrCO3 |
benzopyrene
6-Chlorobenzo[a]pyrene
Conditions | Yield |
---|---|
With copper dichloride In tetrachloromethane for 16h; Heating; | 95% |
With sulfuryl dichloride In 1,2-dichloro-ethane at 20℃; for 1h; Chlorination; | 88% |
With copper dichloride In tetrachloromethane Heating; | 68% |
benzopyrene
A
benzo[a]pyrene-6,12-dione
B
benzopyren-6-yl acetate
C
benzo[a]pyrene-1,6-quinone
D
benzo[a]pyrene-3,6-dione
Conditions | Yield |
---|---|
In acetic acid at 40℃; for 0.166667h; Product distribution; Mechanism; other 6-, 1,6-, and 3,6-substituted benzo<a>pyrenes</a>; | A n/a B 90% C n/a D n/a |
In acetic acid at 40℃; for 0.5h; | A n/a B 90% C n/a D n/a |
benzopyrene
A
benzo[a]pyrene-6,12-dione
B
benzopyren-6-yl acetate
C
benzo[a]pyrene-1,6-quinone
D
benzo[a]pyrene-3,6-dione
Conditions | Yield |
---|---|
With manganese triacetate In acetic acid at 40℃; for 0.5h; Title compound not separated from byproducts; | A n/a B 90% C n/a D n/a |
benzopyrene
7,8,9,10-tetrahydrobenzo[a]pyrene
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide; platinum on activated charcoal In ethyl acetate Product distribution; Ambient temperature; | 86% |
With hydrogen; platinum(IV) oxide; platinum on activated charcoal In ethyl acetate Ambient temperature; | 86% |
With cyclohexane; acetic acid; platinum Hydrogenation; |
benzopyrene
6-Bromobenzo[a]pyrene
Conditions | Yield |
---|---|
With N-Bromosuccinimide In tetrachloromethane for 3h; Heating; | 86% |
With bromine In carbon disulfide Ambient temperature; | 85% |
With pyridinium hydrobromide perbromide In acetic acid for 1h; | 80% |
benzopyrene
[(η5-pentamethylcyclopentadienyl)cobalt(η4:7,11-benzo[a]pyrene)]
Conditions | Yield |
---|---|
In benzene under inert gas; soln. of Co-complex and benzo(a)pyrene in benzene stirred for 24 h; volatiles removed under vac., residue dissolved in Et2O, filtered, filtrate concd., cooled to -30°C; elem. anal.; | 82% |
benzopyrene
6-iodobenzopyrene
Conditions | Yield |
---|---|
With aluminum oxide; N-iodo-succinimide In toluene at 20℃; for 96h; | 80% |
With aluminum oxide; iodine; benzene | |
With aluminum oxide; N-iodo-succinimide In toluene at 20℃; for 48h; | 455.2 mg |
benzopyrene
Conditions | Yield |
---|---|
With nitrosonium tetrafluoroborate In acetonitrile Radical cation formation; | 78% |
Conditions | Yield |
---|---|
With iron(III) chloride; di-tert-butyl peroxide at 20 - 40℃; for 4h; | 77% |
benzopyrene
tert-butyl alcohol
A
9-tert-butylbenzopyrene
B
2,9-di-tert-butylbenzopyrene
Conditions | Yield |
---|---|
In trifluoroacetic acid for 23h; Heating; | A 64% B n/a |
In trifluoroacetic acid for 23h; Heating; | A 64% B 50 mg |
Conditions | Yield |
---|---|
With 1,2-dichloro-benzene; trichlorophosphate at 95 - 100℃; for 2h; | 54% |
With trichlorophosphate | |
With trichlorophosphate |
benzopyrene
Conditions | Yield |
---|---|
With potassium perchlorate In N,N-dimethyl-formamide Addition; Electrochemical reaction; | A 5.6% B 52% C 1.7% |
benzopyrene
A
6-nitrobenzo(a)pyrene
B
3-nitrobenzopyrene
C
1-nitrobenzopyrene
D
3,6-dinitrobenzopyrene
E
1,6-dinitrobenzopyrene
Conditions | Yield |
---|---|
With nitric acid In acetic anhydride for 0.5h; Product distribution; Ambient temperature; other reaction time; | A n/a B n/a C n/a D 13% E 28% |
benzopyrene
6-fluorobenzopyrene
Conditions | Yield |
---|---|
With N-fluoro-2,4-dinitroimidazole In 1,2-dichloro-ethane for 72h; Heating; | 22% |
Multi-step reaction with 2 steps 1: 80 percent / PyHBr3 / acetic acid / 1 h 2: 1.) n-C4H9Li, 2.) perchloryl fluoride / 1.) THF, hexane, -55 deg C, 45 min View Scheme |
benzopyrene
sodium acetate
A
benzo[a]pyrene-6,12-dione
B
benzopyren-6-yl acetate
C
benzo[a]pyrene-1,6-quinone
D
benzo[a]pyrene-3,6-dione
Conditions | Yield |
---|---|
Stage #1: benzo<a>pyrene</a> With iodine; silver perchlorate In benzene Radical cation*AgI formation; Stage #2: sodium acetate In water; acetonitrile Substitution; | A n/a B 11% C n/a D n/a |
benzopyrene
4,5-dihydro(epoxy) benzopyrene
Conditions | Yield |
---|---|
With 18-crown-6 ether; (COCl2)2 In hexane at -10 - -5℃; | 5% |
Conditions | Yield |
---|---|
Stage #1: benzo<a>pyrene</a> With 18-crown-6 ether In N,N-dimethyl-formamide at 20℃; for 20h; Oxidation; Stage #2: (bromomethyl)pentafluorobenzene With triethylamine In toluene at 50℃; for 6h; Esterification; capped tube; | 0.14% |
tetrachloromethane
thiocyanogen
benzopyrene
benzo[def]chrysen-6-ylsulfanyl cyanate
Conditions | Yield |
---|---|
With tetrachloromethane |
The Benzo[a]pyrene, with the CAS registry number 50-32-8, is also known as 1,2-Benzpyrene. It belongs to the product categories of Industrial/Fine Chemicals; Benzo(a)pyrene and other PAH; Organics; Analytical Chemistry; Environmental Endocrine Disruptors; Estradiol, etc. (Environmental Endocrine Disruptors); Highly Purified Reagents; Other Categories; Refined Products by Sublimation; A-BAnalytical Standards; Aromatics Alphabetic; BA - BHChemical Class; Chemical Class; Hydrocarbons; Neats Analytical Standards; PAHs Environmental Standards; PAHs More...Close...; A-B Alphabetic; Alpha Sort; B; A - BH Environmental Standards; PAHs;Volatiles/ Semivolatiles. Its EINECS registry number is 200-028-5. This chemical's molecular formula is C20H12 and molecular weight is 252.31. What's more, its IUPAC name is the same with its product name. This chemical is a five-ring polycyclic aromatic hydrocarbon whose metabolites are mutagenic and highly carcinogenic. It is is mutagenic and highly carcinogenic.It is a potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.
Physical properties about Benzo[a]pyrene are:
(1)ACD/LogP: 6.19; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.188; (4)ACD/LogD (pH 7.4): 6.188; (5)ACD/BCF (pH 5.5): 29700.127; (6)ACD/BCF (pH 7.4): 29700.127; (7)ACD/KOC (pH 5.5): 55358.594; (8)ACD/KOC (pH 7.4): 55358.594; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.887; (14)Molar Refractivity: 90.307 cm3; (15)Molar Volume: 196.094 cm3; (16)Surface Tension: 63.485 dyne/cm; (17)Density: 1.287 g/cm3; (18)Flash Point: 228.566 °C; (19)Enthalpy of Vaporization: 73.351 kJ/mol; (20)Boiling Point: 494.998 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.
Preparation of Benzo[a]pyrene:
This chemical can be prepared by 9,10-Dihydro-benzo[def]chrysene. This reaction needs solvent dimethylformamide at ambient temperature. The reaction time is 20 hours. The yield is 86 %.
Uses of Benzo[a]pyrene:
(1) it is used to determine chemical lipid and used for calibrating instrument and device; (2) it is used to produce other chemicals. For example, it can produce 4,5-Dihydro-benzo[def]chrysene. The reaction occurs with reagent H2 and solvent ethyl acetate at ambient temperature. The yield is 100 %.
Safety information of Benzo[a]pyrene:
When you are dealing with Benzo[a]pyrene, you should be very careful. This chemical may present an immediate or delayed danger to one or more components of the environment. It may catch fire in contact with air, only need brief contact with an ignition source and have a very low flash point or evolve highly flammable gases in contact with water. In addition, it is irritating to eyes, skin and at low levels cause damage to health. It may cause harm to the unborn child and may cause lung damage if swallowed. Repeated exposure may cause your skin dryness or cracking and its vapours may cause drowsiness and dizziness. Therefore, you should avoid exposuring and releasing to the environment. This material and its container must be disposed of as hazardous waste. If swallowed, you can not induce vomiting and you can seek medical advice immediately and show this container or label. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell seek medical advice immediately.
You can still convert the following datas into molecular structure:
(1) SMILES: c1ccc2c(c1)cc3ccc4cccc5c4c3c2cc5
(2) InChI: InChI=1S/C20H12/c1-2-7-17-15(4-1)12-16-9-8-13-5-3-6-14-10-11-18(17)20(16)19(13)14/h1-12H
(3) InChIKey: FMMWHPNWAFZXNH-UHFFFAOYSA-N
The toxicity data of Benzo[a]pyrene is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
frog | LDLo | intrarenal | 9mg/kg (9mg/kg) | Cancer Research. Vol. 24, Pg. 1969, 1964. | |
mouse | LDLo | intraperitoneal | 500mg/kg (500mg/kg) | Toxicology and Applied Pharmacology. Vol. 23, Pg. 288, 1972. | |
rat | LD50 | subcutaneous | 50mg/kg (50mg/kg) | Zeitschrift fuer Krebsforschung. Vol. 69, Pg. 103, 1967. |
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