Benzo[a]pyrene

Base Information

• Chemical Name: Benzo[a]pyrene
• CAS No.: 50-32-8
• Deprecated CAS: 819804-28-9
• Molecular Formula: C20H12
• Molecular Weight: 252.315
• Hs Code.: 29029090
• European Community (EC) Number: 200-028-5
• ICSC Number: 0104
• NSC Number: 21914
• UN Number: 3077
• UNII: 3417WMA06D
• DSSTox Substance ID: DTXSID2020139
• Nikkaji Number: J2.297G
• Wikipedia: Benzo(a)pyrene
• Wikidata: Q306051
• NCI Thesaurus Code: C29800
• Pharos Ligand ID: 2DFJ71262PDN
• Metabolomics Workbench ID: 51974
• ChEMBL ID: CHEMBL31184
• Mol file: 50-32-8.mol

Synonyms:3,4 Benzopyrene;3,4 Benzpyrene;3,4-Benzopyrene;3,4-Benzpyrene;Benzo(a)pyrene

Chemical Property of Benzo[a]pyrene

Chemical Property:

• Appearance/Colour: yellow to brown powder.
• Vapor Pressure: 2.4 at 25 °C (McVeety and Hites, 1988)
• Melting Point: 176 ºC
• Refractive Index: 1.8530 (estimate)
• Boiling Point: 494.998 ºC at 760 mmHg
• PKA: >15 (Christensen et al., 1975)
• Flash Point: 228.566 ºC
• PSA: 0.00000
• Density: 1.287 g/cm³
• LogP: 5.73720
• Storage Temp.: APPROX 4°C
• Solubility.: Soluble in benzene, toluene, and xylene; sparingly soluble in ethanol and methanol (Windholz et al., 1983)
• Water Solubility.: Soluble in benzene, toluene, and xylene. Sparingly soluble in alcohol, methanol. Insoluble in water
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 252.093900383
• Heavy Atom Count: 20
• Complexity: 372
• Transport DOT Label: Class 9

Purity/Quality:

Benzopyrene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,F
• Hazard Codes: T,N,F
• Statements: 45-46-50/53-60-61-43-67-66-36-11-65-38-52/53-36/37/38
• Safety Statements: 45-53-61-60-26-62-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C3=C4C(=CC2=C1)C=CC5=C4C(=CC=C5)C=C3
• Recent ClinicalTrials: Bioavailabity of the Major Metabolites of a Botanical Extract, in Healthy Adults
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. This substance is carcinogenic to humans. May cause heritable genetic damage to human germ cells. May cause toxicity to human reproduction or development.
• Description: Benzo[a]pyrene belongs to the class of polycyclic aromatic hydrocarbons (PAHs). It is produced during incomplete combustion or pyrolysis of organic material and found in nature from the eruption of volcanoes and forest fires. Man-made benzo[a]pyrene is formed by burning plants, wood, coal, and operating cars, trucks and other vehicles. It is also present in some foods (e.g. smoked and barbecued meals), in a few pharmaceutical products, and in tobacco smoke. It is considered as potent mutagen and carcinogen. Benzo[a]pyrene containing extender oil is used for the rubber/plastic production to achieve the desired elasticity at a cheaper price. Benzo[a]pyrene containing coal tar pitch is used in many paints or coatings as corrosion protection coats, such as hydraulic equipment, pipework, steel pilings in ports, vessels, and sealcoat products. Benzo[a]pyrene can be used as wood-preservatives to prevent wood parasites and the wood from drying out. Benzo(a)pyrene (BaP) is bioactivated to its carcinogenic form by phase 1 and phase 2 metabolism. As with other polycyclic aromatic hydrocarbons (PAHs), the presence of the ‘bay region’ contributes greatly to the carcinogenicity of BaP. This region is sterically constrained, allowing the formation of diol epoxides, which subsequently react with intracellular molecules such as DNA. Human exposure to BaP and other PAHs occurs primarily from smoking or from secondhand smoke, air polluted with combustion products, or food and water polluted with combustion products, such as those cooked over charcoal or broiled. BaP has been extensively studied for its toxicities in children and during pregnancy. A study of pregnant active smokers showed that BaP crossed the human placenta and was bound to fetal hemoglobin at levels significantly higher than in pregnant nonsmokers.
• Physical properties: Odorless, yellow, orthorhombic or monoclinic crystals from ethanol. Solution in concentrated sulfuric acid is orange-red and fluoresces green under exposure to UV light (quoted, Keith and Walters, 1992).
• Uses: Benzopyrene is a polyaromatic hydrocarbon (PAH) found in coal tar. Benzopyrene is a known carcinogen. The metbolism of Benzopyrene results in diol epoxides that react and bind to DNA forming adducts which in turns leads to mutations and eventually cancer. BaP is not commercially produced; it is a by-product of combustion. Its primary uses include toxicological mechanistic studies and cancer studies, as a positive control in carcinogenicity studies. There is no known commercial use for BaP. Extensively used in cancer research and for GC (Gas Chromatography) and LC (Liquid Chromatography) Analysis. It is also a multipurpose intermediate.

Technology Process of Benzo[a]pyrene

There total 93 articles about Benzo[a]pyrene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

2-[2,6-di(2-methoxyethenyl)phenyl]naphthalene → benzopyrene (50-32-8,42299-33-2,34505-58-3)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 25 ℃; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol5018273

Reference yield: 65.0%

5-ethynylchrysene (1393794-15-4) → benzopyrene (50-32-8,42299-33-2,34505-58-3)

Guidance literature:

With platinum(II) chloride; In toluene; at 80 ℃;

DOI:10.1016/j.tet.2012.05.130

Reference yield: 60.0%

9,10-dihydro benzopyrene (17573-15-8) → benzopyrene (50-32-8,42299-33-2,34505-58-3)

Guidance literature:

palladium on activated charcoal; at 300 - 305 ℃;

DOI:10.1021/jo00171a040

upstream raw materials:

1,6,10b,11,12,12a-hexahydro-2H-benzo[def]chrysen-3-one

2'-ethyl-3,4,5,6,7,8-hexahydro-1H-spiro[anthracene-2,1'-cyclopentane]

5-hydroxy-3-oxo-2,3,11,12-tetrahydro-1H-benzo[def]chrysene-12a-carboxylic acid methyl ester

4,5-dihydro(epoxy) benzopyrene

Downstream raw materials:

1-acetylbenzopyrene

benzopyren-6-yl acetate

6-Chlorobenzo[a]pyrene

6-Bromobenzo[a]pyrene

Refernces

• 1、 Murai, Masahito,Hosokawa, Naoki,Roy, David,Takai, Kazuhiko. "Bismuth-catalyzed synthesis of polycyclic aromatic hydrocarbons (PAHs) with a phenanthrene backbone via cyclization and aromatization of 2-(2-arylphenyl)vinyl ethers". supporting information. p. 4134 - 4137. Retrieved 2014/09/30.
• 2、 Takasuga, Takumi,Umetsu, Norihito,Makino, Tetsuya,Tsubota, Katsuya,Sajwan, Kenneth S.,Kumar, Kurunthachalam Senthil. "Role of temperature and hydrochloric acid on the formation of chlorinated hydrocarbons and polycyclic aromatic hydrocarbons during combustion of paraffin powder, polymers, and newspaper". . p. 8 - 21. Retrieved 2008/02/09.