227-09-8

Basic information

• Product Name: 1,2:8,9-DIBENZOPENTACENE
• Synonyms: 1,2,8,9-DIBENZOPENTACENE;1,2:8,9-DIBENZOPENTACENE;DIBENZO-(A,L)PENTACENE;1,2,8,9-Dibenzpentacene;1,2:8,9-Dibenzpentacene;Dibenzo(a1)pentacene;Dibenzo-1,2,8,9-pentacene;Dibenzopentacene
• CAS NO: 227-09-8
• Molecular Formula: C₃₀H₁₈
• Molecular Weight: 378.46
• EINECS: 205-933-9
• Mol File: 227-09-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 677 °C at 760 mmHg
• Flash Point: 360.6 °C
• Appearance: /
• Density: 1.286 g/cm³
• Vapor Pressure: 2E-17mmHg at 25°C
• Refractive Index: 1.867
• CAS DataBase Reference: 1,2:8,9-DIBENZOPENTACENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:8,9-DIBENZOPENTACENE(227-09-8)
• EPA Substance Registry System: 1,2:8,9-DIBENZOPENTACENE(227-09-8)

Safety Data

• Hazardous Substances Data: 227-09-8(Hazardous Substances Data)

Usage

General Description

1,2:8,9-Dibenzopentacene is a chemical compound classified under the family of polycyclic aromatic hydrocarbons, which comprise multiple fused benzene rings. It is an organic semi-conducting material with impressive photophysical properties. This chemical has gained significant interest due to its potential use in various applications such as organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and organic photovoltaics (OPVs). Currently, available data about its detailed environmental and health impact is limited, but as with any chemical compound, safe handling practices are required. It's also noteworthy that 1,2:8,9-Dibenzopentacene is not easily produced and is primarily used for research purposes.

InChI:InChI=1/C30H18/c1-3-7-27-19(5-1)9-11-21-13-23-16-26-18-30-22(12-10-20-6-2-4-8-28(20)30)14-24(26)15-25(23)17-29(21)27/h1-18H

Synthetic route

8,17-dihydro-8,17-methanodibenzo[a,l]pentacen-19-one → 1,2:8,9-dibenzopentacene (227-09-8)

Conditions	Yield
In neat (no solvent) at 200℃; for 0.25h; Inert atmosphere;	100%

1,3-bis-(2-methyl-[1]naphthoyl)-benzene → 1,2:8,9-dibenzopentacene (227-09-8) + dibenzo[c,m]dibenzo[d,d’]phenanthrene (222-51-5)

Conditions	Yield
Erhitzen auf Siedetemperatur unter Abdestillieren des entstehenden Wassers;

1,4-bis-(2-methyl-[1]naphthoyl)-benzene → 1,2:8,9-dibenzopentacene (227-09-8) + dibenzo[c,m]dibenzo[d,d’]phenanthrene (222-51-5)

Conditions	Yield
Erhitzen auf Siedetemperatur unter Abdestillieren des entstehenden Wassers;

1.3-bis-<2-methyl-naphthoyl-(1)>-benzene → 1,2:8,9-dibenzopentacene (227-09-8) + dibenzo[c,m]dibenzo[d,d’]phenanthrene (222-51-5)

1.4-bis-<2-methyl-naphthoyl-(1)>-benzene → 1,2:8,9-dibenzopentacene (227-09-8) + dibenzo[c,m]dibenzo[d,d’]phenanthrene (222-51-5)

7.9.16.18-tetraoxo-7.9.16.18-tetrahydro-dibenzopentacene → 1,2:8,9-dibenzopentacene (227-09-8) + 8,17-dihydro-dibenzo[a,l]pentacene

Conditions	Yield
With sodium chloride; zinc(II) chloride; zinc at 210 - 310℃;

dibenzo[a,l]pentacene-7,9,16,18-tetraone (81682-86-2) + zinc-powder + NaCl + ZnCl2 → 1,2:8,9-dibenzopentacene (227-09-8) + 8,17-dihydro-dibenzo[a,l]pentacene

Conditions	Yield
at 310℃;

19,19-dimethoxy-8,17-dihydro-8,17-methanodibenzo[a,l]pentacene → 1,2:8,9-dibenzopentacene (227-09-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: trimethylsilyl iodide / dichloromethane / 3 h / 20 - 45 °C / Schlenk technique; Inert atmosphere 2: neat (no solvent) / 0.25 h / 200 °C / Inert atmosphere View Scheme

maleic anhydride (108-31-6) + 1,2:8,9-dibenzopentacene (227-09-8) → (+/-)-8,17-dihydro-8,17-ethano-dibenzo[a,l]pentacene-19r,20c-dicarboxylic acid-anhydride

Conditions	Yield
With 1,2,4-Trimethylbenzene

1,2:8,9-dibenzopentacene (227-09-8) → dibenzo[a,l]pentacene-8,17-dione (65492-98-0)

Conditions	Yield
With air; xylene Einwirkung von Sonnenlicht;
With selenium(IV) oxide; nitrobenzene

maleic anhydride (108-31-6) + 1,2:8,9-dibenzopentacene (227-09-8) → C34H20O3

Conditions	Yield
In various solvent(s) at 91.5℃; Mechanism; Rate constant; analogous reaction of other polycyclic aromatic hydrocarbons; structure/reactivity correlations, application of theoretical models;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,7,8-tetrachlorodibenzofuran (58802-20-3)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 2,4,6,8-tetrachlorodibenzofuran (58802-19-0)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 2,3,7,8-Tetrachlorodibenzofuran (51207-31-9)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,4-tetrachlorodibenzofuran (24478-72-6)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,4-tetrachloronaphthalene (20020-02-4)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,3,5,8-tetrachloronaphthalene (31604-28-1)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,5-tetrachloronaphthalene (53555-63-8)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,4-trichloronaphthalene (50402-51-2)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3-trichloro-naphthalene (50402-52-3)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,6-trichloronaphthalene (51570-44-6)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,4,6,7-tetrachloronaphthalene (55720-43-9)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,7-trichloronaphthalene (55720-34-8)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,6,7-trichloronaphthalene (55720-39-3)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,5-trichloronaphthalene (55720-33-7)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,8-trichloronaphthalene (55720-35-9)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,3,6,7-tetrachloronaphthalene (55720-42-8)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,7-Tetrachloronaphthalene (55720-41-7)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,4,6-tetrachloronaphthalene (51570-45-7)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,5,7-pentachloronaphthalene (53555-65-0)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,5,7-tetrachloro-naphthalene (67922-23-0)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,4,8-tetrachloronaphthalene (6529-87-9)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,4,7-tetrachloronaphthalene (67922-21-8)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,5,6-tetrachloronaphthalene (67922-22-9)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

1,2:8,9-dibenzopentacene (227-09-8) → 1,2,3,4,6-Pentachloronaphthalene (67922-26-3)

Conditions	Yield
With oxygen; pyrographite; copper(l) chloride at 400℃; for 2h; Oxidation; chlorination; Formation of xenobiotics;

Upstream product

• 81682-86-2 dibenzo[a,l]pentacene-7,9,16,18-tetraone 

Downstream Products

• 149864-78-8 1,2,3,6-tetrachloronaphthalene 
• 150224-23-0 1,2,3,6,8-pentachloronaphthalene 
• 150224-18-3 1,2,3,5,6-pentachloronaphthalene 
• 149864-81-3 1,2,3,8-tetrachloronaphthalene 
• 149864-82-4 1,2,7,8-tetrachloronaphthalene 
• 150224-22-9 1,2,4,6,8-pentachloronaphthalene 
• 150224-24-1 1,2,3,5,8-Pentachloro-naphthalene 
• 150224-25-2 1,2,4,5,8-pentachloronaphthalene 
• 150224-19-4 1,2,4,5,7-pentachloronaphthalene 
• 70648-20-3 1,3,4,7,9-pentachlorodibenzofuran 
• 70648-15-6 1,3,4,6,9-pentachlorodibenzofuran 
• 83704-49-8 1,2,3,4,9-pentachlorodibenzofuran 
• 70872-82-1 1,2,6,7,9-pentachlorodibenzofuran 
• 70648-23-6 1,2,4,8,9-pentachlorodibenzofuran 

Relevant articles and documents

A Practical General Method for the Preparation of Long Acenes

The field of long acenes, the narrowest of the zig-zag graphene nanoribbons, has been an area of significant interest in the past decade because of its potential applications in organic electronics, spintronics and plasmonics. However the low solubility and high reactivity of these compounds has so far hindered their preparation on large scales. We report here a concise strategy for the synthesis of higher acenes through Diels–Alder condensation of arynes with a protected tetraene ketone. After deprotection by cleavage of the ketal, the obtained monoketone precursors cleanly yield the corresponding acenes through quantitative cheletropic thermal decarbonylation in the solid state, at moderate temperatures of 155 to 205 °C. This approach allows the preparation of heptacene, benzo[a]hexacene, cis- and trans-dibenzopentacene and offers a valuable new method for the synthesis of even larger acenes.