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.
• General Description: Benzo[a]pyrene (B[a]P) is a polycyclic aromatic hydrocarbon (PAH) known for its carcinogenic properties, with its metabolic activation involving the formation of reactive intermediates such as dihydrodiols and oxides, particularly in the K-region (e.g., 4,5-dihydrodiols and 4,5-oxide). The stereochemical configuration of these metabolites plays a critical role in their biological activity and carcinogenic potential, as specific stereoisomers are more prone to DNA adduct formation and mutagenesis. Understanding these configurations provides insights into the mechanisms of B[a]P-induced toxicity and carcinogenicity.

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:

benzopyren-6-yl acetate

4,5-dihydrobenzopyrene

7,8,9,10-tetrahydrobenzo[a]pyrene

benzpyrene-6-carbaldehyde

Refernces

ABSOLUTE CONFIGURATION OF THE K-REGION 4,5-DIHYDRODIOLS AND 4,5-OXIDE OF BENZOPYRENE

10.1016/0040-4039(81)80111-6

The study focuses on determining the absolute configuration of the K-region 4,5-dihydrodiols and the 4,5-oxide derivatives of Benzo[a]pyrene (B[a]P). It discusses the methods used to resolve the stereoisomers and the biological implications of these configurations, particularly in the context of carcinogenesis.