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

Chemical Properties

Yellow Solid

Uses

9,10-Dihydrobenzo[a]pyrene is an environmental carcinogens oxidized by CYP2S1. Metabolized to Benzopyrene (B205800) by rat liver microsomes.

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

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

Downstream Products

• 57405-01-3 C₃₄H₂₃BrO₄ 
• 57405-08-0 (+/-)-trans-7,8-Dihydrobenzopyrene-7,8-diol dibenzoate 
• 57404-88-3 (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene 
• 63268-36-0 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (7R,8R)-8-hydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-7-yl ester 
• 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 
• 63268-38-2 7,8-bis-benzoyloxy-7,8-dihydro benzo[a]pyrene 
• 63268-37-1 C₃₄H₂₂O₄ 
• 169437-81-4 trans-(7R,8R)-7,8-dibenzoyloxy-7,8,9,10-tetrahydrobenzopyrene 
• 63268-35-9 trans-(7S,8S)-7,8-dibenzoyloxy-7,8,9,10-tetrahydrobenzopyrene 
• 63323-30-8 (7R,8S)-dihydroxy-(9S,10R)-epoxy-7,8,9,10-tetrahydrodibenzo[a]pyrene 
• 62314-67-4 (+/-)-trans-7,8-Dihydrobenzo[a]pyrene-7,8-diol 
• 60864-95-1 (-)-7R-trans-Benzopyrene-7,8-dihydrodiol 
• 63323-31-9 (-)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 68906-75-2 (7R,8S)-7,8-epoxy-7,8,9,10-tetrahydrobenzopyrene 

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.