193-39-5

Basic information

• Product Name: Indenopyrene
• Synonyms: 1,10-(1,2-Phenylene)pyrene;1,10-(o-Phenylene)pyrene
• CAS NO: 193-39-5
• Molecular Formula: C₂₂H₁₂
• Molecular Weight: 276.09
• EINECS: 205-893-2
• Mol File: 193-39-5.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 497.101 °C at 760 mmHg
• Flash Point: 247.24 °C
• Appearance: Yellow crystals
• Density: 1.379 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 2.009
• CAS DataBase Reference: Indenopyrene(CAS DataBase Reference)
• NIST Chemistry Reference: Indenopyrene(193-39-5)
• EPA Substance Registry System: Indenopyrene(193-39-5)

Safety Data

• Hazardous Substances Data: 193-39-5(Hazardous Substances Data)

Usage

General Description

Indenopyrene, also known as benzo[b]fluoranthene, is a polycyclic aromatic hydrocarbon (PAH) that is often found as a byproduct of incomplete combustion of organic materials such as fossil fuels, tobacco, and wood. It is classified as a Group 2B carcinogen by the International Agency for Research on Cancer, indicating that it is possibly carcinogenic to humans. Indenopyrene has been linked to various health effects, including respiratory issues, DNA damage, and cancer. It is considered a priority pollutant by the US Environmental Protection Agency, and efforts are being made to reduce its emissions and exposure to protect human health and the environment.

InChI:InChI=1/C22H12/c1-2-7-17-16(6-1)19-12-15-9-8-13-4-3-5-14-10-11-18(22(17)19)21(15)20(13)14/h1-12H

Synthetic route

Trifluoro-methanesulfonic acid 2-pyren-1-yl-phenyl ester → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 135 - 140℃; for 6h;	91%

2-(pyren-1-yl)aniline (102662-21-5) → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With tert.-butylnitrite In acetonitrile at 20℃; for 10h;	85%
With sulfuric acid; acetic acid; sodium nitrite anschliessendes Erwaermen mit Kupfer-Pulver;

C22H15N + phenylacetylene (536-74-3) → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tert.-butylnitrite In acetonitrile at 20℃; for 15h; Sealed tube; Irradiation;	84%

1-bromo-2-(1-pyrenyl)benzene (377737-93-4) → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 140℃; for 11h; Inert atmosphere;	72%

1-bromopyrene (1714-29-0) + (2-bromophenyl)boronic acid (244205-40-1) → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; tricyclohexylphosphine; tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl-formamide at 155℃; for 48h;	51%

endo-(8bSR,8cSR,12bRS,12aRS)-8b,8c,11,12,12a,12b-hexahydrobenzocyclobuta<1,2-e>pyrene (92681-17-9, 93861-97-3) → 4-phenylpyrene (7267-88-1) + Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform Heating;	A 10% B 4%

4-phenylpyrene (7267-88-1) → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With aluminium trichloride; sodium chloride at 120℃;

indeno[1,2,3-cd]pyrene-11,12-dicarboxylic acid-anhydride (5695-26-1) → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With soda lime

pyrene (129-00-0) + benzene (71-43-2) → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
at 750℃;

phenanthrene (85-01-8) → pyrene (129-00-0) + naphthalene (91-20-3) + Indeno[1,2,3-cd]pyrene (193-39-5) + anthracene (120-12-7)

Conditions	Yield
at 850℃; Further byproducts given;

7,8,9,10-tetrahydroindeno[1,2,3-cd]pyrene (112312-98-8) → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone benzene,reflux,30 min.;

C22H18 (95676-43-0) → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone benzene,reflux,30 min.;

2-(pyren-1-yl)cyclohexanone (111189-39-0) → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With PPA; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1) 100 deg C,2h 2) benzene,reflux,30 min; Yield given. Multistep reaction;
With PPA; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1.) 110 deg C, 2 h, 2.) benzene, reflux, 30 min; Yield given. Multistep reaction;

2-(pyren-1-yl)cyclohexanone (111189-39-0) → Indeno[1,2,3-cd]pyrene (193-39-5) + 7,8,9,10-tetrahydroindeno[1,2,3-cd]pyrene (112312-98-8) + C22H18 (95676-43-0)

Conditions	Yield
With PPA at 100℃; for 2h;

2-(4-pyrenyl)cyclohexanone (111189-40-3) → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone Multistep reaction;
With PPA; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1.) 110 deg C, 2 h, 2.) benzene, reflux, 30 min; Yield given. Multistep reaction;

polyethylene → Indeno[1,2,3-cd]pyrene (193-39-5) + benzo[e]pyrene (192-97-2) + PERYLENE (198-55-0) + Benzo[ghi]perylene (191-24-2)

Conditions	Yield
With air at 600 - 900℃; Oxidation; Formation of xenobiotics; Further byproducts given;

waste wood chips → Indeno[1,2,3-cd]pyrene (193-39-5) + benzopyrene (50-32-8) + dibenzo[a,h]anthracene (53-70-3) + Benzo[ghi]perylene (191-24-2)

Conditions	Yield
With air Oxidation; Formation of xenobiotics; Further byproducts given;

Eucalyptus grandis wood → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
Decomposition; Formation of xenobiotics; pyrolysis;

wood → pyrene (129-00-0) + Indeno[1,2,3-cd]pyrene (193-39-5) + 1,7-dimethylphenanthrene (483-87-4) + Retene (483-65-8)

Conditions	Yield
With air Oxidation; Formation of xenobiotics; Further byproducts given;

Pennzoil Perfomax SAE 5W-40 synthetic oil + leaded gasoline 91 octane → benzo[e]acephenanthrylene (205-99-2) + Indeno[1,2,3-cd]pyrene (193-39-5) + fluoranthene (206-44-0) + Benzo[ghi]perylene (191-24-2)

Conditions	Yield
With air Oxidation; Formation of xenobiotics; Further byproducts given. Title compound not separated from byproducts;

Mogul Forte GX SAE 15W-40 mineral oil + leaded gasoline 91 octane → benzo[e]acephenanthrylene (205-99-2) + Indeno[1,2,3-cd]pyrene (193-39-5) + fluoranthene (206-44-0) + Benzo[ghi]perylene (191-24-2)

Conditions	Yield
With air Oxidation; Formation of xenobiotics; Further byproducts given. Title compound not separated from byproducts;

artificial solid municipal waste → Indeno[1,2,3-cd]pyrene (193-39-5) + benzopyrene (50-32-8) + dibenzo[a,h]anthracene (53-70-3) + Benzo[ghi]perylene (191-24-2)

Conditions	Yield
With air at 780℃; Formation of xenobiotics; Further byproducts given. Title compound not separated from byproducts;

tyre rubber → Indeno[1,2,3-cd]pyrene (193-39-5) + benzopyrene (50-32-8) + dibenzo[a,h]anthracene (53-70-3) + Benzo[ghi]perylene (191-24-2)

Conditions	Yield
With carbon dioxide at 900℃; Formation of xenobiotics; Further byproducts given. Title compound not separated from byproducts;

Dimethyl ether (115-10-6) → pyrene (129-00-0) + Indeno[1,2,3-cd]pyrene (193-39-5) + benzo[e]pyrene (192-97-2) + 4H-Cyclopenta[def]phenanthrene (203-64-5)

Conditions	Yield
With air at 840℃; under 19501.6 Torr; Formation of xenobiotics; high pressure combustion; Further byproducts given. Title compound not separated from byproducts;

compressed natural gas → pyrene (129-00-0) + naphthalene (91-20-3) + Indeno[1,2,3-cd]pyrene (193-39-5) + benzo[e]pyrene (192-97-2)

Conditions	Yield
With air at 880℃; under 18001.4 Torr; Formation of xenobiotics; high pressure combustion; Further byproducts given. Title compound not separated from byproducts;

polypropylene → Indeno[1,2,3-cd]pyrene (193-39-5)

Conditions	Yield
With silica gel Formation of xenobiotics;

Indeno[1,2,3-cd]pyrene (193-39-5) → C22H11Br (120362-72-3)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 45℃; for 8h;	98%
With bromine In acetic acid for 0.5h;	87%
With N-Bromosuccinimide In benzene for 41h; Heating;	62%

Indeno[1,2,3-cd]pyrene (193-39-5) → C22H11NO2 + C22H11NO2 + 12-Nitroindeno<1,2,3-cd>pyrene

Conditions	Yield
With dinitrogen tetraoxide In dichloromethane for 0.2h; Ambient temperature; Yield given;	A n/a B n/a C 91%
With dinitrogen tetraoxide In dichloromethane for 0.2h; Ambient temperature; Yields of byproduct given;	A n/a B n/a C 91%

Indeno[1,2,3-cd]pyrene (193-39-5) + acetyl chloride (75-36-5) → 8-acetylindeno<1,2,3-cd>pyrene + 12-acetylindeno<1,2,3-cd>pyrene (120362-67-6) + 8,12-diacetylindeno<1,2,3-cd>pyrene

Conditions	Yield
With aluminium trichloride In dichloromethane for 0.5h;	A n/a B 62% C 17%
With aluminium trichloride In dichloromethane at 0℃; for 0.5h;	A n/a B 62% C 17%

Indeno[1,2,3-cd]pyrene (193-39-5) → 1,2-dihydroindeno<1,2,3-cd>pyrene (120362-68-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate under 1551.4 Torr; for 70h; Ambient temperature;	59%

Indeno[1,2,3-cd]pyrene (193-39-5) → C22H12O + C22H12O + 1-2,6-6a-diepoxyindeno<1,2,3-cd>pyrene

Conditions	Yield
With phosphate buffer; potassium peroxomonosulphate; tetra(n-butyl)ammonium hydrogensulfate; acetone In dichloromethane at 8 - 12℃; for 12h;	A 4% B 33% C 3%

Indeno[1,2,3-cd]pyrene (193-39-5) + [1,4]naphthoquinone (130-15-4) → indeno[1,2,3-de]naphtho[2,1,8-qra]naphthacene-5,16-dione (122542-61-4)

Indeno[1,2,3-cd]pyrene (193-39-5) → cis-1,2-dihydro-1,2-dihydroxyindeno<1,2,3-cd>pyrene (102420-54-2)

Conditions	Yield
With osmium(VIII) oxide In pyridine; benzene for 504h; Ambient temperature; Yield given;

Upstream product

• 1714-29-0 1-bromopyrene 
• 824-91-9 O-methoxymethylphenol 
• 95676-43-0 C₂₂H₁₈ 
• 112312-98-8 7,8,9,10-tetrahydroindeno[1,2,3-cd]pyrene 
• 85-01-8 phenanthrene 
• 5695-26-1 indeno[1,2,3-cd]pyrene-11,12-dicarboxylic acid-anhydride 
• 102662-21-5 2-(pyren-1-yl)aniline 
• 7267-88-1 4-phenylpyrene 
• 536-74-3 phenylacetylene 
• 615-43-0 2-iodophenylamine 
• 164461-18-1 1-pyrenylboronic acid 
• 377737-93-4 1-bromo-2-(1-pyrenyl)benzene 
• 120233-50-3 10B,11,12,12a-tetrahydro-indeno[1,2,3-cd]pyrene-11,12-dicarboxylic acid-anhydride 
• 102442-84-2 2′-nitrophenyl-1-pyrene 

Downstream Products

• 1207097-81-1 C₃₄H₂₁N 
• 1207097-83-3 C₄₀H₂₃N 
• 102420-56-4 (+/-)-trans-1,2-dihydro-1,2-dihydroxyindeno<1,2,3-cd>pyrene 
• 99520-63-5 1,2-dihydroindeno<1,2,3-cd>pyrene-1,2-dione 
• 99520-65-7 1-hydroxyindeno<1,2,3-cd>pyrene 
• 95050-14-9 12-Nitroindeno<1,2,3-cd>pyrene 
• 102420-54-2 cis-1,2-dihydro-1,2-dihydroxyindeno<1,2,3-cd>pyrene 
• 120362-67-6 12-acetylindeno<1,2,3-cd>pyrene 

Relevant articles and documents

The 2?s + 2?s Photocycloadditions of Triplet Pyrene to Cyclohexa-1,3-diene

exo-(8bSR,8cSR,12bRS,12aSR)-8b,8c,11,12,12a,12b-Hexahydrobenzocyclobutapyrene and endo-(8bSR,8cSR,12bRS,12aRS)-8b,8c,11,12,12a,12b-hexahydrobenzocyclobutapyrene have been isolated; this is the first example of a 2?s + 2?s photocycloaddition between cyclohexa-1,3-diene and 3pyrene.

Synthesis of cyclopenta-fused polycyclic aromatic hydrocarbons utilizing aryl-substituted anilines

Cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs), potentially electronically and biologically highly active materials, were synthesized from readily available 2-aryl-substituted anilines. Reactions occur under extremely mild, room temperature conditions using tBuONO as the sole reagent. The use of a nitrite source generates a reactive diazonium intermediate in situ that then reacts with a tethered polycyclic aromatic moiety by intramolecular aromatic substitution. This protocol could be presented as one of the simplest methods to access CP-PAHs.

Role of temperature and hydrochloric acid on the formation of chlorinated hydrocarbons and polycyclic aromatic hydrocarbons during combustion of paraffin powder, polymers, and newspaper

Formation of chlorinated hydrocarbons and polycyclic aromatic hydrocarbons (PAHs) were determined using a laboratory-scale incinerator when combusting materials at different temperatures, different concentrations of hydrochloric acid (HCl), and when combusting various types of polymers/newspaper. Polychlorobenzenes (PCBz), polychlorophenols (PCPhs), polychlorinated dibenzo-p-dioxins/furans (PCDD/Fs) and their toxic equivalency (TEQ) and PAHs were highlighted and reported. Our results imply maximum formation of chlorinated hydrocarbons at 400°C in the following order; PCBz≥PCPhs?PCDFs>PCDDs>TEQ on a parts-per-billion level. Similarly, a maximum concentration of chlorinated hydrocarbons was noticed with an HCl concentration at 1000 ppm with the presence of paraffin powder in the following order; PAHs>PCBz≥PCPhs?PCDFs>PCDDs>TEQ an a parts-per-billion level. PAHs were not measured at different temperatures. Elevated PAHs were noticed with different HCl concentrations and paraffin powder combustion (range: 27-32 μg/g). While, different polymers and newspaper combusted, nylon and acrylonitrile butadiene styrene (ABS) produced the maximum hydrogen cyanide (HCN) concentration, concentrations of PCDD/FS, dioxin-like polychlorinated biphenyls (DL-PCBs), and TEQ were in a decreasing order: polyvinylchloride (PVC)newspaperpolyethyleneterephthalate (PET) polyethylene (PE) polypropylene (PP) ABS = blank. Precursors of PCBs were in a decreasing order: PPnylonPEnewspaperABSPVCblankPET. Precursors of PCDD/Fs were in a decreasing order: newspaper PP= nylonPEABSPVC= blankPET. BTX formation was in a decreasing order; PEnylonnewspaperABSPP. PAHs formation were elevated with parts-per-million levels in the decreasing order of PPnylonPE newspaperblankABS PETPVC.