56752-35-3

Basic information

• Product Name: 3,9-Dibromoperylene
• Synonyms: 3,9-Dibromoperylene
• CAS NO: 56752-35-3
• Molecular Formula: C₂₀H₁₀Br₂
• Molecular Weight: 410.1014
• Mol File: 56752-35-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 290 °C
• Boiling Point: 554.4±23.0 °C(Predicted)
• Appearance: /
• Density: 1.795±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 3,9-Dibromoperylene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,9-Dibromoperylene(56752-35-3)
• EPA Substance Registry System: 3,9-Dibromoperylene(56752-35-3)

Safety Data

• Hazardous Substances Data: 56752-35-3(Hazardous Substances Data)

Usage

General Description

3,9-Dibromoperylene is a chemical compound made up of two bromine atoms attached to a perylene molecule. It is a polycyclic aromatic hydrocarbon (PAH) and is a member of the larger family of perylene compounds. This chemical is commonly used in the field of organic electronics and as a fluorescent dye in various applications such as in the manufacturing of OLEDs (organic light-emitting diodes) and in organic photovoltaic devices. 3,9-Dibromoperylene has useful properties such as high thermal stability and strong fluorescence, making it suitable for use in these technological applications. Due to its potential environmental and health hazards, it is important to handle and dispose of 3,9-Dibromoperylene with care and in accordance with safety regulations.

Synthetic route

PERYLENE (198-55-0) → 3,9-dibromoperylene (56752-35-3)

Conditions	Yield
With bromine In acetic acid at 50℃; for 5h;	94%
With N-Bromosuccinimide In tetrahydrofuran Inert atmosphere;	91%
With bromine In tetrachloromethane at 110℃; for 12h;	63%

PERYLENE (198-55-0) → 3,10-Dibromoperylene (85514-20-1) + 3,9-dibromoperylene (56752-35-3) + 3-bromoperylene (23683-68-3)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃;	A n/a B 90% C n/a
With N-Bromosuccinimide In dichloromethane at 20℃; for 2h;	A n/a B n/a C 30%
With N-Bromosuccinimide In dichloromethane at 20℃; for 2h; Yields of byproduct given. Title compound not separated from byproducts;

PERYLENE (198-55-0) → 3,10-Dibromoperylene (85514-20-1) + 3,9-dibromoperylene (56752-35-3)

Conditions	Yield
With bromine In benzene at 40℃; Inert atmosphere;	A 23% B 29%
With bromine
With bromine In benzene at 35℃; for 1.16667h; Inert atmosphere; Overall yield = 26 %; Overall yield = 2.1 g;

perylene-3,9-(SO3H)2 (71506-23-5) → 3,9-dibromoperylene (56752-35-3)

Conditions	Yield
With sulfuric acid; bromine; acetic acid

PERYLENE (198-55-0) + benzene (71-43-2) → 3,10-Dibromoperylene (85514-20-1) + 3,9-dibromoperylene (56752-35-3) + 3,4,9-tribromo-perylene

Conditions	Yield
bei der Bromierung;

PERYLENE (198-55-0) + aluminium bromide (7727-15-3) + nitrobenzene (98-95-3) → 3,9-dibromoperylene (56752-35-3)

Conditions	Yield
Bromierung;

PERYLENE (198-55-0) + dihydrogen peroxide (7722-84-1) + acetic acid (64-19-7) + sodium bromide → 3,9-dibromoperylene (56752-35-3)

Conditions	Yield
at 90℃; Bromierung;

PERYLENE (198-55-0) + bromine (7726-95-6) → 3,10-Dibromoperylene (85514-20-1) + 3,9-dibromoperylene (56752-35-3)

sulfuric acid (7664-93-9) + perylene-3,9-(SO3H)2 (71506-23-5) + bromine (7726-95-6) + acetic acid (64-19-7) → 3,9-dibromoperylene (56752-35-3)

Triisopropyl borate (5419-55-6) + 3,9-dibromoperylene (56752-35-3) → perylene-3,9-diboronic acid

Conditions	Yield
Stage #1: 3,9-dibromoperylene With n-butyllithium In tetrahydrofuran for 0.25h; Stage #2: Triisopropyl borate In tetrahydrofuran	100%

3,9-dibromoperylene (56752-35-3) + di-p-tolylamine (620-93-9) → 3,9-bis(N,N-bis(4-methylphenyl)amino)perylene

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In 1,2-dimethoxyethane; toluene at 110℃; Buchwald-Hartwig Coupling; Inert atmosphere;	83%

3,9-dibromoperylene (56752-35-3) + C24H13NO2 → C68H34N2O4

Conditions	Yield
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In toluene at 88℃; for 14h;	82%

3,9-dibromoperylene (56752-35-3) + bis(4-methoxyphenyl)amine (101-70-2) → 3,9-bis(N,N-bis(4-methoxyphenyl)amino)perylene

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In 1,2-dimethoxyethane; toluene at 110℃; Buchwald-Hartwig Coupling; Inert atmosphere;	81%

3,9-dibromoperylene (56752-35-3) + phenylboronic acid (98-80-6) → C26H15Br

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 70℃; for 11h; Inert atmosphere;	80.56%

3,9-dibromoperylene (56752-35-3) + diphenylamine (122-39-4) → 3,9-bis(N,N-diphenylamino)perylene

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In 1,2-dimethoxyethane; toluene at 110℃; Buchwald-Hartwig Coupling; Inert atmosphere;	79%

3,9-dibromoperylene (56752-35-3) + trimethylsilylacetylene (1066-54-2) → 3,9-bis(trimethylsilylethynyl)perylene

Conditions	Yield
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 60 - 70℃; for 2h; Sonogashira Cross-Coupling;	78%

3,9-dibromoperylene (56752-35-3) + bis-(4-fluoro-phenyl)-amine (330-91-6) → 3,9-bis(N,N-bis(4-fluorophenyl)amino)perylene

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In 1,2-dimethoxyethane; toluene at 110℃; Buchwald-Hartwig Coupling; Inert atmosphere;	78%

3,9-dibromoperylene (56752-35-3) + (6-phenylpyridin-3-yl)boronic acid (155079-10-0) → C42H26N2 (1257879-55-2)

Conditions	Yield
With potassium carbonate; triphenylphosphine; palladium dichloride In ethanol; water; toluene for 4h; Inert atmosphere; Reflux;	75.26%

3,9-dibromoperylene (56752-35-3) + 4-Chlorophenylboronic acid (1679-18-1) → C32H18Cl2 (951039-41-1)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 12h; Heating / reflux;	75%

3,9-dibromoperylene (56752-35-3) + 4-tert-Butylphenylacetylene (772-38-3) → C44H36

Conditions	Yield
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 60 - 70℃; for 2h; Sonogashira Cross-Coupling;	70%

3,10-Dibromoperylene (85514-20-1) + 3,9-dibromoperylene (56752-35-3) + 2,7-dibromo-9,9-dioctylfluorene (198964-46-4) → poly-2,7-(9,9-dioctylfluorene)-co-(perylene), Mn = 47930 g/mol, D = 4.1; monomer(s): 3,9-dibromoperylene 1,5 mol%; 3,10-dibromoperylene, 1.5 mol%; 2,7-dibromo-9,9-dioctylfluorene

Conditions	Yield
Stage #1: 3,10-Dibromoperylene; 3,9-dibromoperylene; 2,7-dibromo-9,9-dioctylfluorene With [2,2]bipyridinyl; cyclooctadiene; bis(1,5-cyclooctadiene)nickel (0) In N,N-dimethyl-formamide; toluene at 85℃; for 24h; Yamamoto polymerization; Stage #2: With bromobenzene In N,N-dimethyl-formamide; toluene Further stages.;	69%

3,10-Dibromoperylene (85514-20-1) + 3,9-dibromoperylene (56752-35-3) + 2,7-dibromo-9,9-dioctylfluorene (198964-46-4) + N,N'-bis(4'-bromophenyl)-1,6,7,12-tetra[4-(1,1,3,3-tetramethylbutyl)phenoxy]perylene-3,4,9,10-tetracarboxdiimide (344454-74-6) → poly-2,7-(9,9-dioctylfluorene)-co-(perylene)-co-[1,6,7,12-tetra(4-tert-octyl)-phenoxy-bis-N,N'-bisphenylperylene-3,4,9,10-dicarboximide], Mn = 46650, D = 7.7; monomer(s): 3,9-dibromoperylene 1,5 mol%; 3,10-dibromoperylene, 1.5 mol%;

Conditions

Yield

Stage #1: 3,10-Dibromoperylene; 3,9-dibromoperylene; 2,7-dibromo-9,9-dioctylfluorene; N,N'-bis(4'-bromophenyl)-1,6,7,12-tetra[4-(1,1,3,3-tetramethylbutyl)phenoxy]perylene-3,4,9,10-tetracarboxdiimide With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0); 1,5-cis,cis-cyclooctadiene In N,N-dimethyl-formamide; toluene at 85℃; for 24h; Yamamoto polymerization; Stage #2: With bromobenzene In N,N-dimethyl-formamide; toluene Further stages.;

67%

3,9-dibromoperylene (56752-35-3) + 4,4’-dicyanodipehnylamine (36602-05-8) → 3,9-bis(N,N-bis(4-cyanophenyl)amino)perylene

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In 1,2-dimethoxyethane; toluene at 110℃; Buchwald-Hartwig Coupling; Inert atmosphere;	60%

3,9-dibromoperylene (56752-35-3) + 4-methoxyphenylboronic acid (5720-07-0) → 3,9-bis(4-methoxyphenyl)perylene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; for 8h; Suzuki-Miyaura Coupling;	57%

3,10-Dibromoperylene (85514-20-1) + 3,9-dibromoperylene (56752-35-3) + C63H92BNO4 → C77H88BrNO2

Conditions	Yield
Stage #1: 3,10-Dibromoperylene; 3,9-dibromoperylene; C63H92BNO4 With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate In ethanol; toluene at 90℃; for 4h; Suzuki Coupling; Inert atmosphere; Stage #2: With iron(III) chloride In nitromethane; dichloromethane at 20℃; for 2h;	55%

3,9-dibromoperylene (56752-35-3) + bis(pinacol)diborane (73183-34-3) → 3,9-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)perylene

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos In 1,4 dimethylcyclohexane for 12h; Reflux;	50.83%
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos In 1,4-dioxane for 12h; Reflux;	50.83%

3,9-dibromoperylene (56752-35-3) + allyl alcohol (107-18-6) → C26H24O2

Conditions	Yield
Stage #1: allyl alcohol With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran for 18h; Suzuki Coupling; Inert atmosphere; Cooling; Reflux; Stage #2: 3,9-dibromoperylene With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate Suzuki Coupling; Inert atmosphere; Reflux;	41%

3,6,9,12-tetraoxapentadec-14-yn-1-amine (1013921-36-2) + 3,9-dibromoperylene (56752-35-3) → C42H50N2O8

Conditions	Yield
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 60 - 70℃; for 6h; Sonogashira Cross-Coupling;	38%

5-Hexen-1-ol (821-41-0) + 3,9-dibromoperylene (56752-35-3) → 6-[9-(6-Hydroxy-hexyl)-perylen-3-yl]-hexan-1-ol

Conditions	Yield
Stage #1: 5-Hexen-1-ol With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran for 18h; Suzuki Coupling; Inert atmosphere; Cooling; Reflux; Stage #2: 3,9-dibromoperylene With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate Suzuki Coupling; Inert atmosphere; Reflux;	30%

3,9-dibromoperylene (56752-35-3) + 1,2-bis(4-butylphenyl)ethyne (80221-11-0) → 1,2,7,8-tetrakis(4-n-butylphenyl)dicyclopenta[cd,lm]perylene (1361026-35-8) + 1,2,8,9,10,11-hexakis(4-n-butylphenyl)benzo[b]cyclopenta[lm]perylene (1361026-36-9)

Conditions	Yield
With triethylamine; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium(0) In toluene; acetonitrile at 111℃; for 16h; Inert atmosphere;	A 18% B n/a

3,9-dibromoperylene (56752-35-3) + diphenyl acetylene (501-65-5) → 7-(1,2-diphenylvinyl)-1,2-diphenylcyclopenta[cd]perylene (1361026-34-7) + 1,2,7,8-tetraphenylbiscyclopenta[cd,lm]perylene (1361026-33-6)

Conditions	Yield
With triethylamine; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium(0) In toluene; acetonitrile at 111℃; for 16h; Inert atmosphere;	A n/a B 17%

3,9-dibromoperylene (56752-35-3) → perylene-3,9-dione (5796-92-9)

3,9-dibromoperylene (56752-35-3) → 3,9-dibromo-4,10-dinitro-perylene (858857-30-4)

Conditions	Yield
With sulfuric acid; acetic acid; potassium nitrate

3,9-dibromoperylene (56752-35-3) + benzoyl chloride (98-88-4) → isoviolanthrone (128-64-3)

Conditions	Yield
With aluminium trichloride at 150 - 170℃;

3,9-dibromoperylene (56752-35-3) + benzoyl chloride (98-88-4) → 3,9-dibenzoyl-4,10-dibromo-perylene (856340-89-1)

Conditions	Yield
With carbon disulfide; aluminium trichloride

Upstream product

• 198-55-0 PERYLENE 
• 71-43-2 benzene 
• 7664-93-9 sulfuric acid 
• 71506-23-5 perylene-3,9-(SO₃H)2 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 7722-84-1 dihydrogen peroxide 
• 7727-15-3 aluminium bromide 
• 98-95-3 nitrobenzene 

Downstream Products

• 128-64-3 isoviolanthrone 
• 856340-89-1 3,9-dibenzoyl-4,10-dibromo-perylene 
• 198-55-0 PERYLENE 
• 951039-41-1 C₃₂H₁₈Cl₂ 
• 1361026-35-8 1,2,7,8-tetrakis(4-n-butylphenyl)dicyclopenta[cd,lm]perylene 
• 1361026-36-9 1,2,8,9,10,11-hexakis(4-n-butylphenyl)benzo[b]cyclopenta[lm]perylene 
• 1361026-34-7 7-(1,2-diphenylvinyl)-1,2-diphenylcyclopenta[cd]perylene 
• 1361026-33-6 1,2,7,8-tetraphenylbiscyclopenta[cd,lm]perylene 
• 1257879-55-2 C₄₂H₂₆N₂ 

Relevant articles and documents

Aromaticity Relocation in Perylene Derivatives upon Two-Electron Oxidation To Form Anthracene and Phenanthrene

We prepared perylene dications 12+and 22+by using “capped” perylene derivatives, and for the first time, successfully obtained single crystals of a perylene dication 12+that enabled us to perform its structural analysis. We realized that the substituted aryl groups on perylene control the positions of positive charges, thus the remaining electronic system satisfies Clar's sextet rule toward the highest number of localized sextets. Experimental and theoretical evidence proved that Clar's aromatic π-sextet rule could be applied even for the dicationic perylenes in a very simple way.

MOLECULES AND OLIGOMERS FOR ENDOTHERMIC SINGLET FISSION

The present disclosure relates to a composition that includes a repeat unit defined by where each of R1, R2, R3, R4, R5, R6, R7, and R8 includes at least one of a hydrogen atom, a fluorine atom, and/or a first hydrocarbon chain having between 1 and 20 carbon atoms, inclusively, where each of A1, A2, A3 and A4 are either a carbon atom or a nitrogen atom, when A1 is a nitrogen atom, A2 is a carbon atom, when A2 is a nitrogen atom, A1 is a carbon atom, when A3 is a nitrogen atom, A4 is a carbon atom, when A4 is a nitrogen atom, A3 is a carbon atom, either A1 or A2 form a covalent bond, x, with a carbon atom, a, either A3 or A4 form a covalent bond, y, with a carbon atom, b, L is a linker group that includes an aromatic ring, and n is between 1 and 20, inclusively.

Reliable and reproducible separation of 3,9-and 3,10-dibromoperylenes and the photophysical properties of their alkynyl derivatives

We developed a reliable and reproducible method for the separation of 3,9-dibromoperylene and 3,10-dibromoperylene resulting from bromination of perylene by using sequential and repeated recrystallization. Because of the unprecedented purities of the dibromoperylenes, they exhibit the high-est melting temperatures so far reported. In addition, various alkynylperylenes were prepared from the dibromoperylenes, and we investigated the photophysical characteristics of these alkynyl derivatives in detail.