193-43-1

Basic information

• Product Name: INDENO(1,2,3-C,D)FLUORANTHENE
• Synonyms: INDENO(1,2,3-C,D)FLUORANTHENE;Indeno[1,2,3-cd]fluoranthene (purity);91208, Indeno[1,2,3-cd]fluoranthene (pur ity);1,2:5,6-Dibenzopyracylene
• CAS NO: 193-43-1
• Molecular Formula: C₂₂H₁₂
• Molecular Weight: 276.33
• Product Categories: Analytical Standards;Alphabetic;I
• Mol File: 193-43-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 261-262 °C
• Boiling Point: 872.2 °C at 760 mmHg
• Flash Point: 405.1 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 9.99E-30mmHg at 25°C
• Refractive Index: 1.823
• Storage Temp.: 2-8°C
• BRN: 1970675
• CAS DataBase Reference: INDENO(1,2,3-C,D)FLUORANTHENE(CAS DataBase Reference)
• NIST Chemistry Reference: INDENO(1,2,3-C,D)FLUORANTHENE(193-43-1)
• EPA Substance Registry System: INDENO(1,2,3-C,D)FLUORANTHENE(193-43-1)

Safety Data

• Hazardous Substances Data: 193-43-1(Hazardous Substances Data)

Usage

Uses

Indeno[1,2,3-cd]fluoranthene is a potential carcinogen and used for analytical tests in vehicle emissions.

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

Synthetic route

1,4-dibromonaphthalene (83-53-4) + 2-Chlorobenzeneboronic acid (3900-89-8) → indeno[123-cd]fluoranthene (193-43-1)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; (bis(tricyclohexyl)phosphine)palladium(II) dichloride In various solvent(s) at 155℃; for 72h;	100%

1,4-dibromonaphthalene (83-53-4) + (2-bromophenyl)boronic acid (244205-40-1) → fluoranthene (206-44-0) + indeno[123-cd]fluoranthene (193-43-1)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); 1,8-diazabicyclo[5.4.0]undec-7-ene; tricyclohexylphosphine In N,N-dimethyl-formamide at 155℃; for 48h; Suzuki coupling, Heck coupling;	A 35% B 51%

1,4-bis(2-fluorophenyl)naphthalene (1380586-81-1) → indeno[123-cd]fluoranthene (193-43-1)

Conditions	Yield
With aluminum oxide at 200℃; for 60h; Inert atmosphere;	34%

dibenzo[b,def]chrysene-7,14-dione (128-66-5) → indeno[123-cd]fluoranthene (193-43-1) + 13H-naphto<3,2,1-cd>fluoranthene-13-one (13227-56-0)

Conditions	Yield
at 1200℃;	A 17% B 4.5%
at 1200℃; Product distribution; further temp., vacuum flow app.;	A 17% B 4.5%

benzopentaphene-5,8-dione (3302-52-1) → indeno[123-cd]fluoranthene (193-43-1) + 13H-naphto<3,2,1-cd>fluoranthene-13-one (13227-56-0)

Conditions	Yield
at 1200℃;	A 6% B 2%

2-fluoranthen-3-yl-aniline (744255-53-6) → indeno[123-cd]fluoranthene (193-43-1)

Conditions	Yield
With sulfuric acid; acetic acid; sodium nitrite anschliessendes Erwaermen mit Kupfer-Pulver;

2-nitrophenyl bromide (577-19-5) → indeno[123-cd]fluoranthene (193-43-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper-powder / 210 - 220 °C 2: Raney nickel; ethanol / Hydrogenation 3: NaNO2; aqueous H2SO4; acetic acid / anschliessendes Erwaermen mit Kupfer-Pulver View Scheme

3-iodo-fluoranthene (63277-99-6) → indeno[123-cd]fluoranthene (193-43-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper-powder / 210 - 220 °C 2: Raney nickel; ethanol / Hydrogenation 3: NaNO2; aqueous H2SO4; acetic acid / anschliessendes Erwaermen mit Kupfer-Pulver View Scheme

3-(2-nitro-phenyl)-fluoranthene (744255-82-1) → indeno[123-cd]fluoranthene (193-43-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney nickel; ethanol / Hydrogenation 2: NaNO2; aqueous H2SO4; acetic acid / anschliessendes Erwaermen mit Kupfer-Pulver View Scheme

C22H20O4 → indeno[123-cd]fluoranthene (193-43-1)

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl acetamide; toluene at 75℃; Sealed tube; Inert atmosphere;	33.9 mg

indeno[123-cd]fluoranthene (193-43-1) → 2-Nitro-indeno<1.2.3-cd>fluoranthen (22865-38-9)

Conditions	Yield
With nitric acid; acetic anhydride

indeno[123-cd]fluoranthene (193-43-1) → 2-Amino-indeno<1,2,3-cd>fluoranthen (22865-39-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3, Ac2O 2: SnCl2, aq. HCl View Scheme

indeno[123-cd]fluoranthene (193-43-1) → 2-Fluor-indeno<1.2.3-cd>fluoranthen (22865-40-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: HNO3, Ac2O 2: SnCl2, aq. HCl 3: (i) aq. NaNO2, aq. HBF4, (ii) (heating) View Scheme

Upstream product

• 1380586-81-1 1,4-bis(2-fluorophenyl)naphthalene 
• 83-53-4 1,4-dibromonaphthalene 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 3302-52-1 benzopentaphene-5,8-dione 
• 744255-53-6 2-fluoranthen-3-yl-aniline 
• 744255-82-1 3-(2-nitro-phenyl)-fluoranthene 
• 63277-99-6 3-iodo-fluoranthene 
• 577-19-5 2-nitrophenyl bromide 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 128-66-5 dibenzo[b,def]chrysene-7,14-dione 

Downstream Products

• 22865-38-9 2-Nitro-indeno<1.2.3-cd>fluoranthen 

Relevant articles and documents

Benzannulation via ruthenium-catalyzed diol-diene [4+2] cycloaddition: One- and two-directional syntheses of fluoranthenes and acenes

A new benzannulation protocol is described and applied to the synthesis of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol-diene [4+2] cycloaddition delivers cyclohex-1-ene-4,5-diols, which are subject to aromatization upon dehydration or Nicholas diol deoxydehydration. Employing diol and tetraol reactants, benzannulation can be conducted efficiently in one- and two-directional modes, respectively, as illustrated in the construction of substituted fluoranthenes and acenes.

Oligoindenopyrenes: A new class of polycyclic aromatics

(Graph Presented) A new class of polycyclic aromatic hydrocarbons - oligoindenopyrenes - has been synthesized featuring a Pd-catalyzed Suzuki - Heck coupling cascade. The oligoindenopyrenes are robust, highly colored substructures of C70 and have properties that might prove useful in new organic materials or devices. After excitation, the tetraindenopyrene derivative 3d undergoes efficient deactivation (99%) by internal conversion to the ground state. The small fluorescence quantum yield (0.004) is in accordance with the short (0.6 ns) fluorescence decay time.

Verwendung von Bis(1,2,4,6-tetramethyl-1,4-dihydro-4-pyridinyl) als Reduktionsmittel zur Erzeugung organischer Radikalanionen fuer EPR-Spektroskopie

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