1,5-Dibromoanthracene supplier

Name
1,5-Dibromoanthracene
EINECS
CAS No. 3278-82-8
Article Data6
CAS DataBase
Density 1.768 g/cm³
Solubility
Melting Point 209 °C
Formula C₁₄H₈Br₂
Boiling Point 438.755 °C at 760 mmHg
Molecular Weight 336.026
Flash Point 256.192 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,5-DIBROMOANTHRACENE
PSA 0.00000
LogP 5.51800

Synthetic route

: 602-77-7
1,5-dibromo-9,10-anthraquinone

: 3278-82-8
1,5-dibromoanthraquinone

Conditions

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%

: 41063-80-3, 41063-81-4
1,5-Dibrom-9,10-dihydro-anthracen-9,10-diol

: 3278-82-8
1,5-dibromoanthraquinone

Conditions

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

: 82-46-2
1,5-Dichloroanthraquinone

: 3278-82-8
1,5-dibromoanthraquinone

Conditions

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

: 129-44-2
1,5-diaminoanthraquinone

: 3278-82-8
1,5-dibromoanthraquinone

Conditions

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

: 3278-82-8
1,5-dibromoanthraquinone

: 1066-54-2
trimethylsilylacetylene

: 1,5-bis((trimethylsilyl)ethynyl)anthracene

Conditions

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

: 110-89-4
piperidine

: 3278-82-8
1,5-dibromoanthraquinone

: 1,5-bis(piperidyl)anthracene

Conditions

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%

: 3278-82-8
1,5-dibromoanthraquinone

: 73183-34-3
bis(pinacol)diborane

: 1,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene

Conditions

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%

: 3278-82-8
1,5-dibromoanthraquinone

: 135883-45-3
1-(tert-butylsulfanyl)-4-ethynylbenzene

: C38H34S2

Conditions

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%

: 419536-33-7
4-(carbazol-9-yl)phenylboronic acid

: 3278-82-8
1,5-dibromoanthraquinone

: 1,5-bis[4-(9H-carbazole-9-yl)phenyl]anthracene

Conditions

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

: 3278-82-8
1,5-dibromoanthraquinone

: 3923-52-2
1,1-diphenyl-2-propyn-1-ol

: 1,5-bis[(diphenylhydroxymethyl)ethynyl]anthracene

Conditions

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

: 3278-82-8
1,5-dibromoanthraquinone

: 95-92-1
oxalic acid diethyl ester

: diethyl anthrylene-1,5-diglyoxylate

Conditions

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%

: 3278-82-8
1,5-dibromoanthraquinone

: 16419-60-6
2-Methylphenylboronic acid

: 1,5-di-o-tolyl-anthracene

Conditions

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

: 56041-85-1
4-ethynylthioanisole

: 3278-82-8
1,5-dibromoanthraquinone

: C32H22S2

Conditions

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%

: 3278-82-8
1,5-dibromoanthraquinone

: C32H46BNO5

: 1,5-bis(N-(1-hexylheptyl)-3-methoxy-1,8-naphthalimide-4-yl)anthracene

Conditions

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

: 5390-04-5
pent-1-yn-5-ol

: 3278-82-8
1,5-dibromoanthraquinone

: C24H22O2

Conditions

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%

: 13461-74-0
9-ethynylfluoren-9-ol

: 3278-82-8
1,5-dibromoanthraquinone

: 1,5-bis[(9-hydroxyfluoren-9-yl)ethynyl]anthracene

Conditions

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

: 3278-82-8
1,5-dibromoanthraquinone

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: anthracene-1,5-dicarbaldehyde

Conditions

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%

: 3278-82-8
1,5-dibromoanthraquinone

: 609-08-5
Diethyl methylmalonate

: 18107-18-1
diazomethyl-trimethyl-silane

: C26H31BrO4Si

Conditions

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

...Expand

: 3278-82-8
1,5-dibromoanthraquinone

: 1079-66-9
chloro-diphenylphosphine

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

Conditions

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%

: 3278-82-8
1,5-dibromoanthraquinone

: 98-80-6
phenylboronic acid

: 1,5-diphenylanthracene

Conditions

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

: 3278-82-8
1,5-dibromoanthraquinone

: 609-08-5
Diethyl methylmalonate

: 18107-18-1
diazomethyl-trimethyl-silane

: C38H54O8Si2

Conditions

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

...Expand

: 3278-82-8
1,5-dibromoanthraquinone

: 106-51-4
p-benzoquinone

: (+/-)-6,11-dibromotriptycene-1,4-quinone

Conditions

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

: C48H59NO2

: 3278-82-8
1,5-dibromoanthraquinone

: C62H66BrNO2

Conditions

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

: 2510-22-7
4-pyridylacetylene

: 3278-82-8
1,5-dibromoanthraquinone

: 926021-77-4
1,5-bis[2-(4-pyridyl)ethynyl]anthracene

Conditions

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

: 117043-89-7
9-methyl-7H-benzo[c]carbazole

: 3278-82-8
1,5-dibromoanthraquinone

: C48H32N2

Conditions

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%

: 3278-82-8
1,5-dibromoanthraquinone

: 2-formylnaphthyl-3-boronic acid pinacol ester

: 3,3'-(anthracene-1,5-diyl)bis(2-naphthaldehyde)

Conditions

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

: 3278-82-8
1,5-dibromoanthraquinone

: 40138-16-7
2-formylbenzene boronic acid

: 2,2'-(anthracene-1,5-diyl)dibenzaldehyde

Conditions

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

: 74-85-1
ethene

: 3278-82-8
1,5-dibromoanthraquinone

A: (+)(9R,10R)-1,5-dibromo-9,10-dihydro-9,10-ethanoanthracene

B: (-)(9S,10S)-1,5-dibromo-9,10-dihydro-9,10-ethanoanthracene

Conditions

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

...Expand

: 3278-82-8
1,5-dibromoanthraquinone

: C20H12Br2O2

Conditions

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

: 3278-82-8
1,5-dibromoanthraquinone

: (+/-)-1,6-dibromo-11,14-ditetradecyloxytriptycene

Conditions

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

1,5-Dibromoanthracene Specification

The 1,5-Dibromoanthracene, with the CAS registry number 3278-82-8, is also known as Anthracene, 1,5-dibromo-. It belongs to the product category of Anthracenes. This chemical's molecular formula is C₁₄H₈Br₂ and molecular weight is 336.02. What's more, its IUPAC name is the same with its product name. It should be kept in a ventilated and dry place.

Physical properties about 1,5-Dibromoanthracene are: (1)ACD/LogP: 6.223; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.22; (4)ACD/LogD (pH 7.4): 6.22; (5)ACD/BCF (pH 5.5): 31590.99; (6)ACD/BCF (pH 7.4): 31590.99; (7)ACD/KOC (pH 5.5): 57859.08; (8)ACD/KOC (pH 7.4): 57859.08; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å²; (13)Index of Refraction: 1.749; (14)Molar Refractivity: 77.318 cm³; (15)Molar Volume: 190.035 cm³; (16)Polarizability: 30.651×10^-24cm³; (17)Surface Tension: 54.329 dyne/cm; (18)Density: 1.768 g/cm³; (19)Flash Point: 256.192 °C; (20)Enthalpy of Vaporization: 66.877 kJ/mol; (21)Boiling Point: 438.755 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: c1cc2cc3c(cccc3Br)cc2c(c1)Br
(2) InChI: InChI=1S/C14H8Br2/c15-13-5-1-3-9-7-12-10(8-11(9)13)4-2-6-14(12)16/h1-8H
(3) InChIKey: DIMYVOCPPKNNPF-UHFFFAOYSA-N

Product Name

1,5-Dibromoanthracene

Synthetic route

1,5-Dibromoanthracene Specification

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