17573-15-8

Basic information

• Product Name: 9,10-dihydrobenzo(a)pyrene
• Synonyms: 9,10-dihydrobenzo(a)pyrene
• CAS NO: 17573-15-8
• Molecular Formula: C₂₀H₁₄
• Molecular Weight: 254.33
• Product Categories: Aromatics, Heterocycles, Mutagenesis Research Chemicals
• Mol File: 17573-15-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 450.7°Cat760mmHg
• Flash Point: 218.9°C
• Appearance: /
• Density: 1.258g/cm³
• Vapor Pressure: 6.86E-08mmHg at 25°C
• Refractive Index: 1.831
• Storage Temp.: Refrigerator
• Solubility: Benzene, Chloroform, Tetrahydrofuran
• CAS DataBase Reference: 9,10-dihydrobenzo(a)pyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-dihydrobenzo(a)pyrene(17573-15-8)
• EPA Substance Registry System: 9,10-dihydrobenzo(a)pyrene(17573-15-8)

Safety Data

• Hazardous Substances Data: 17573-15-8(Hazardous Substances Data)

Usage

Description

9,10-Dihydrobenzo(a)pyrene is a chemical compound that is classified as an environmental carcinogen. It is a yellow solid and is known to be oxidized by the enzyme CYP2S1. 9,10-dihydrobenzo(a)pyrene is metabolized to benzopyrene by rat liver microsomes, which is a significant aspect of its chemical properties and potential environmental impact.

Uses

Used in Environmental Research and Toxicology:
9,10-Dihydrobenzo(a)pyrene is used as a research compound for studying the effects of environmental carcinogens on human health and the environment. Its role in the metabolism and oxidation process by CYP2S1 makes it a valuable subject for understanding the mechanisms of carcinogen activation and detoxification in the body.
Used in Pharmaceutical and Chemical Industries:
9,10-Dihydrobenzo(a)pyrene is used as a reference compound in the pharmaceutical and chemical industries for the development of new drugs and chemical products that can target or mitigate the harmful effects of environmental carcinogens. Its properties and interactions with biological systems can provide insights into the design of more effective treatments and preventive measures against cancer.
Used in Analytical Chemistry:
As a yellow solid with specific chemical properties, 9,10-dihydrobenzo(a)pyrene can be used in analytical chemistry for the calibration of instruments and the development of new analytical methods for detecting and quantifying environmental carcinogens in various samples, such as air, water, and soil.
Used in Material Science:
The unique chemical and physical properties of 9,10-dihydrobenzo(a)pyrene may also find applications in material science, particularly in the development of new materials with specific optical, electronic, or structural properties that can be utilized in various industrial applications.

InChI:InChI=1/C20H14/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/h1,3-6,8-12H,2,7H2

Upstream product

• 6272-55-5 7-hydroxy-7,8,9,10-tetrahydrobenzopyrene 
• 221347-73-5 6-bromo-9,10-dihydrobenzopyrene 
• 110-86-1 pyridine 
• 221347-72-4 6-bromo-7,8,9,10-tetrahydrobenzopyren-7-ol 
• 3331-46-2 9,10-dihydrobenzo[a]pyren-(8H)-none 
• 3443-45-6 1-pyrenebutyric acid 
• 64709-55-3 1-pyreneacetic acid 
• 59275-39-7 4-(1-pyrene)butanoic acid ethyl ester 
• 87337-16-4 1-pyrenylacetaldehyde 
• 87337-17-5 ethyl 3-hydroxy-4-(1-pyrenyl)butanoate 
• 87337-23-3 ethyl 3-bromo-4-(1-pyrenyl)butanoate 
• 64709-56-4 ethyl 1-pyrenylacetate 

Downstream Products

• 57405-00-2 (+/-)-7,8,9,10-Tetrahydrobenzopyrene-trans-7,8-diol dibenzoate 
• 50-32-8 benzopyrene 
• 36504-67-3 7,8-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 68906-75-2 (7R,8S)-7,8-epoxy-7,8,9,10-tetrahydrobenzopyrene 
• 68906-81-0 (7S,8R)-7,8-epoxy-7,8,9,10-tetrahydrobenzopyrene 
• 63323-31-9 (-)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 60864-95-1 (-)-7R-trans-Benzopyrene-7,8-dihydrodiol 
• 62314-67-4 (+/-)-trans-7,8-Dihydrobenzo[a]pyrene-7,8-diol 
• 63323-30-8 (7R,8S)-dihydroxy-(9S,10R)-epoxy-7,8,9,10-tetrahydrodibenzo[a]pyrene 
• 63268-35-9 trans-(7S,8S)-7,8-dibenzoyloxy-7,8,9,10-tetrahydrobenzopyrene 
• 169437-81-4 trans-(7R,8R)-7,8-dibenzoyloxy-7,8,9,10-tetrahydrobenzopyrene 
• 63268-37-1 C₃₄H₂₂O₄ 
• 63268-38-2 7,8-bis-benzoyloxy-7,8-dihydro benzo[a]pyrene 
• 63227-55-4 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (7S,8S)-8-hydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-7-yl ester 

Relevant articles and documents

Carbon-13 labeled benzo[a]pyrenes and derivatives. 4. Labeling the 7-10 positions

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Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal-Free Catalyst under Air

Graphene oxide (GO) has been developed as an inexpensive, environmental friendly, metal-free carbocatalyst for the dehydrogenation of nitrogen heterocycles. Valuable compounds, such as quinoline, 3,4-dihydroisoquinoline, quinazoline, and indole derivatives, have been successfully used as substrates. The investigation of various oxygen-containing molecules with different conjugated systems indicated that both the oxygen-containing groups and large π-conjugated system in GO sheets are essential for this reaction. (Figure presented.).

Synthesis of (±)-trans-7,8-dihydrodiol of 6-fluoro-benzo[a]pyrene via hydroxyl-directed regioselective functionalization of substituted pyrene

Synthesis of (±)-trans-7,8-dihydroxy-6-fluoro-7,8- dihydrobenzo[a]pyrene, the metabolite from 6-fluoro-benzo[a]pyrene, is described. Position 6 of 7,8,9,10-tetrahydrobenzo[a]pyren-7-ol (1) was functionalized by bromination with N-bromosaccharin. Regioselectivity in the bromination is thought to derive from a substrate-reagent hydrogen bond. NMR evidence is offered to support this model. The 6-bromo derivative 2 was subjected to dehydration followed by bromine-lithium exchange. Quenching the lithio intermediate with NFSi afforded the 6-fluoro derivative 4. Prevost reaction on the 7,8 double bond resulted in the trans dibenzoate 5 (established by comparison to a cis derivative prepared by osmium tetroxide cis dihydroxylation). Introduction of the 9,10 double bond by a bromination- dehydrobromination procedure, followed by hydrolysis, gave racemic trans- 7,8-dihydrodiol 7. Resolution of the enantiomers was achieved by chiral HPLC, and the absolute configurations of the early and late eluting isomers were determined through CD spectroscopy by comparison with the metabolically obtained (7R,8R)-dihydrodiol.