3278-82-8

Basic information

• Product Name: 1,5-DIBROMOANTHRACENE
• Synonyms: 1,5-DIBROMOANTHRACENE
• CAS NO: 3278-82-8
• Molecular Formula: C₁₄H₈Br₂
• Molecular Weight: 336.02
• Product Categories: Anthracenes
• Mol File: 3278-82-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 209 °C
• Boiling Point: 438.755 °C at 760 mmHg
• Flash Point: 256.192 °C
• Appearance: /
• Density: 1.768 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.749
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane (Slightly, Sonicated), Chloroform (Slightly), DMSO (Slightly, He
• CAS DataBase Reference: 1,5-DIBROMOANTHRACENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-DIBROMOANTHRACENE(3278-82-8)
• EPA Substance Registry System: 1,5-DIBROMOANTHRACENE(3278-82-8)

Safety Data

• Hazardous Substances Data: 3278-82-8(Hazardous Substances Data)

Usage

General Description

1,5-Dibromoanthracene is a polycyclic aromatic hydrocarbon compound that consists of two bromine atoms attached to an anthracene molecule. It is a yellow solid at room temperature and is typically used as a building block in the synthesis of various organic compounds, including pharmaceuticals, dyes, and fluorescent materials. The presence of the two bromine atoms makes 1,5-Dibromoanthracene a useful intermediate in organic chemistry for creating new molecules with specific properties. It is also known to have potential applications in organic light-emitting diodes (OLEDs) and organic photovoltaic devices due to its favorable electronic properties. However, it is important to handle 1,5-Dibromoanthracene with caution, as it is considered toxic and can pose health risks if not handled properly.

InChI:InChI=1/C14H8Br2/c15-13-5-1-3-9-7-12-10(8-11(9)13)4-2-6-14(12)16/h1-8H

Synthetic route

1,5-dibromo-9,10-anthraquinone (602-77-7) → 1,5-dibromoanthraquinone (3278-82-8)

Conditions	Yield
Stage #1: 1,5-dibromo-9,10-anthraquinone With sodium tetrahydroborate In isopropyl alcohol at 0 - 20℃; for 3.5h; Stage #2: With acetic acid; tin(ll) chloride for 2h; Reflux;	71%
With hydrogen bromide; hypophosphorous acid; acetic acid at 120℃; for 96h;	46%
Stage #1: 1,5-dibromo-9,10-anthraquinone With sodium tetrahydroborate; isopropyl alcohol at 20℃; for 4h; Cooling with ice; Stage #2: With acetic acid; tin(ll) chloride for 4h; Reflux;	23%

1,5-Dibrom-9,10-dihydro-anthracen-9,10-diol (41063-80-3, 41063-81-4) → 1,5-dibromoanthraquinone (3278-82-8)

Conditions	Yield
With hypophosphorous acid; potassium iodide
With acetic acid; tin(ll) chloride for 2h; Reflux;	10 g

1,5-Dichloroanthraquinone (82-46-2) → 1,5-dibromoanthraquinone (3278-82-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: KBr, CuCl2, 85 percent H3PO4 / nitrobenzene / 40 h / 195 - 205 °C 2: 1) NaBH4, 2) KI, NaH2PO2 / 2) MeOH View Scheme
Multi-step reaction with 2 steps 1: KBr, CuCl2, 85 percent H3PO4 / nitrobenzene / 92 h / 195 - 205 °C 2: 1) NaBH4, 2) KI, NaH2PO2 / 2) MeOH View Scheme
Multi-step reaction with 3 steps 1: KBr, CuCl2 2: KBH4 3: KI, H3PO2 View Scheme

1,5-diaminoanthraquinone (129-44-2) → 1,5-dibromoanthraquinone (3278-82-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 2.5 h / 65 °C 2: sodium tetrahydroborate / isopropyl alcohol / 3.5 h / 0 - 20 °C 3: acetic acid; tin(ll) chloride / 2 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 2.5 h / 65 °C 2: hypophosphorous acid; acetic acid; hydrogen bromide / 96 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 2.5 h / 20 - 65 °C 2.1: sodium tetrahydroborate; isopropyl alcohol / 4 h / 20 °C / Cooling with ice 2.2: 4 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: copper(I) bromide; tert.-butylnitrite / acetonitrile / 2 h / 65 °C 2.1: sodium tetrahydroborate / isopropyl alcohol / 3.5 h / 0 - 20 °C 2.2: 2 h / Reflux View Scheme

1,5-dibromoanthraquinone (3278-82-8) + trimethylsilylacetylene (1066-54-2) → 1,5-bis((trimethylsilyl)ethynyl)anthracene

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran; toluene for 8h; Inert atmosphere; Reflux;	94%

piperidine (110-89-4) + 1,5-dibromoanthraquinone (3278-82-8) → 1,5-bis(piperidyl)anthracene

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; sodium t-butanolate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;	91%

1,5-dibromoanthraquinone (3278-82-8) + bis(pinacol)diborane (73183-34-3) → 1,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 16h; Miyaura Borylation Reaction; Schlenk technique; Inert atmosphere;	89%

1,5-dibromoanthraquinone (3278-82-8) + 1-(tert-butylsulfanyl)-4-ethynylbenzene (135883-45-3) → C38H34S2

Conditions	Yield
With copper(l) iodide; bis(tri-t-butylphosphine)palladium(0); diisopropylamine In toluene at 20℃; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;	87%

4-(carbazol-9-yl)phenylboronic acid (419536-33-7) + 1,5-dibromoanthraquinone (3278-82-8) → 1,5-bis[4-(9H-carbazole-9-yl)phenyl]anthracene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 14h; Inert atmosphere;	86%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 14h; Inert atmosphere;	1.8 g

1,5-dibromoanthraquinone (3278-82-8) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → 1,5-bis[(diphenylhydroxymethyl)ethynyl]anthracene

Conditions	Yield
With copper(l) iodide; triethylamine; triphenylphosphine; palladium diacetate In toluene at 90℃; for 4h; Substitution;	83%

1,5-dibromoanthraquinone (3278-82-8) + oxalic acid diethyl ester (95-92-1) → diethyl anthrylene-1,5-diglyoxylate

Conditions	Yield
Stage #1: 1,5-dibromoanthraquinone With n-butyllithium In tetrahydrofuran; hexane at -94℃; for 4h; Inert atmosphere; Stage #2: oxalic acid diethyl ester In tetrahydrofuran; hexane at -94 - 20℃; for 1.5h; Inert atmosphere;	80%

1,5-dibromoanthraquinone (3278-82-8) + 2-Methylphenylboronic acid (16419-60-6) → 1,5-di-o-tolyl-anthracene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In toluene at 120℃; for 6h;	79%

4-ethynylthioanisole (56041-85-1) + 1,5-dibromoanthraquinone (3278-82-8) → C32H22S2

Conditions	Yield
With copper(l) iodide; bis(tri-t-butylphosphine)palladium(0); diisopropylamine In toluene at 20℃; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;	79%

1,5-dibromoanthraquinone (3278-82-8) + C32H46BNO5 → 1,5-bis(N-(1-hexylheptyl)-3-methoxy-1,8-naphthalimide-4-yl)anthracene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	68%

pent-1-yn-5-ol (5390-04-5) + 1,5-dibromoanthraquinone (3278-82-8) → C24H22O2

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine In tetrahydrofuran for 13h; Sonogashira Cross-Coupling; Reflux; Inert atmosphere; Schlenk technique;	68%

9-ethynylfluoren-9-ol (13461-74-0) + 1,5-dibromoanthraquinone (3278-82-8) → 1,5-bis[(9-hydroxyfluoren-9-yl)ethynyl]anthracene

Conditions	Yield
With copper(l) iodide; triethylamine; triphenylphosphine; palladium diacetate In toluene at 90℃; for 4h; Substitution;	67%

1,5-dibromoanthraquinone (3278-82-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → anthracene-1,5-dicarbaldehyde

Conditions	Yield
Stage #1: 1,5-dibromoanthraquinone With n-butyllithium In diethyl ether at 0 - 20℃; for 1.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In diethyl ether at -78℃; for 1.5h; Inert atmosphere;	63%
Stage #1: 1,5-dibromoanthraquinone With n-butyllithium In diethyl ether at -10 - 20℃; for 1.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In diethyl ether at -78 - 20℃; for 1.5h; Inert atmosphere;	61%

1,5-dibromoanthraquinone (3278-82-8) + Diethyl methylmalonate (609-08-5) + diazomethyl-trimethyl-silane (18107-18-1) → C26H31BrO4Si

Conditions	Yield
With palladium diacetate; sodium hydride; 4-(N,N-Dimethylamino)triphenylphosphine In toluene at 60℃; for 12h; Molecular sieve;	63%

1,5-dibromoanthraquinone (3278-82-8) + chloro-diphenylphosphine (1079-66-9) → 1,5-Bis-diphenylphosphonio-anthracen (1183-21-7)

Conditions	Yield
Stage #1: 1,5-dibromoanthraquinone With n-butyllithium In diethyl ether at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: chloro-diphenylphosphine In diethyl ether at -78 - 20℃; Inert atmosphere; Schlenk technique;	62%

1,5-dibromoanthraquinone (3278-82-8) + phenylboronic acid (98-80-6) → 1,5-diphenylanthracene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 94℃; for 1h; Inert atmosphere;	61%

1,5-dibromoanthraquinone (3278-82-8) + Diethyl methylmalonate (609-08-5) + diazomethyl-trimethyl-silane (18107-18-1) → C38H54O8Si2

Conditions	Yield
With palladium diacetate; sodium hydride; 4-(N,N-Dimethylamino)triphenylphosphine In cyclohexane at 60℃; for 12h; Molecular sieve;	60%

1,5-dibromoanthraquinone (3278-82-8) + p-benzoquinone (106-51-4) → (+/-)-6,11-dibromotriptycene-1,4-quinone

Conditions	Yield
With acetic acid; copper(l) chloride for 2h; Diels-Alder reaction; Reflux;	56%

C48H59NO2 + 1,5-dibromoanthraquinone (3278-82-8) → C62H66BrNO2

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In toluene at 80℃; for 20h; Sonogashira coupling;	52%

4-pyridylacetylene (2510-22-7) + 1,5-dibromoanthraquinone (3278-82-8) → 1,5-bis[2-(4-pyridyl)ethynyl]anthracene (926021-77-4)

Conditions	Yield
With copper(l) iodide; triphenylphosphine; palladium diacetate In triethylamine; toluene for 24h; Sonogashira reaction; Heating;	45%

9-methyl-7H-benzo[c]carbazole (117043-89-7) + 1,5-dibromoanthraquinone (3278-82-8) → C48H32N2

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate for 12h; Reflux; Inert atmosphere;	40%
With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate In o-xylene; toluene at 120℃; for 12h; Inert atmosphere;	40%

1,5-dibromoanthraquinone (3278-82-8) + 2-formylnaphthyl-3-boronic acid pinacol ester → 3,3'-(anthracene-1,5-diyl)bis(2-naphthaldehyde)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; water; toluene for 16h; Suzuki Coupling; Reflux; Inert atmosphere;	40%

1,5-dibromoanthraquinone (3278-82-8) + 2-formylbenzene boronic acid (40138-16-7) → 2,2'-(anthracene-1,5-diyl)dibenzaldehyde

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; water; toluene for 16h; Suzuki Coupling; Reflux; Inert atmosphere;	18%

ethene (74-85-1) + 1,5-dibromoanthraquinone (3278-82-8) → (+)(9R,10R)-1,5-dibromo-9,10-dihydro-9,10-ethanoanthracene + (-)(9S,10S)-1,5-dibromo-9,10-dihydro-9,10-ethanoanthracene

Conditions	Yield
In toluene at 180℃; under 61504.9 Torr; for 67h;

1,5-dibromoanthraquinone (3278-82-8) → C20H12Br2O2

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; copper(l) chloride / 2 h / Reflux 2: acetic acid; zinc / tetrahydrofuran / 2 h / 20 °C View Scheme

1,5-dibromoanthraquinone (3278-82-8) → (+/-)-1,6-dibromo-11,14-ditetradecyloxytriptycene

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; copper(l) chloride / 2 h / Reflux 2: acetic acid; zinc / tetrahydrofuran / 2 h / 20 °C 3: potassium carbonate; potassium iodide / butanone / 22 h / Reflux View Scheme

Upstream product

• 129-44-2 1,5-diaminoanthraquinone 
• 82-46-2 1,5-Dichloroanthraquinone 
• 602-77-7 1,5-dibromo-9,10-anthraquinone 
• 41063-80-3 1,5-Dibrom-9,10-dihydro-anthracen-9,10-diol 

Downstream Products

• 1183-21-7 1,5-Bis-diphenylphosphonio-anthracen 

Relevant articles and documents

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