131276-24-9

Usage

Uses

Used in Coordination Chemistry:
1,8-Bis(diphenylphosphino)anthra is used as a ligand for forming complexes with metals, which is crucial in coordination chemistry. The formation of these complexes can lead to materials with unique properties that are valuable in various applications.
Used in Industrial Applications:
1,8-Bis(diphenylphosphino)anthra is used as a component in the development of materials with specific properties for industrial applications. Its ability to coordinate with metals results in compounds that are often utilized in catalysis, a process vital for many chemical reactions and transformations in the industry.
Used in Catalyst Development:
In the field of catalysis, 1,8-Bis(diphenylphosphino)anthra is used as a ligand to create catalysts that can facilitate and enhance the rate of chemical reactions. The complexes formed with metals can exhibit high selectivity and activity, making them valuable in various chemical processes.
Used in Research and Development:
1,8-Bis(diphenylphosphino)anthra is also used in research and development settings to explore new coordination chemistry and investigate the properties of metal complexes. This can lead to the discovery of new materials and applications in various scientific and industrial fields.

Synthetic route

1,8-dibromoanthraquinone (38313-16-5) → 1,8-dibromoanthraquinone (131276-24-9)

Conditions	Yield
With Al(c-C6H11O)3; cyclohexanol for 72h; Heating;	77%
Stage #1: 1,8-dibromoanthraquinone With sodium tetrahydroborate In methanol at -78℃; Stage #2: With hydrogenchloride In methanol Heating; Stage #3: With sodium tetrahydroborate In methanol; diethylene glycol dimethyl ether at 20℃;	6.6 g
With aluminum isopropoxide; cyclohexanol for 72h; Reflux;

1,8-dibromo-10-anthrone (869061-20-1) → 1,8-dibromoanthraquinone (131276-24-9)

Conditions	Yield
Stage #1: 1,8-dibromo-10-anthrone With sodium tetrahydroborate In propan-1-ol Stage #2: With hydrogenchloride	76%

1,8-dichloroanthraquinone (82-43-9) → 1,8-dibromoanthraquinone (131276-24-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 62 percent / CuCl2; KBr; H3PO4 / nitrobenzene / Heating 2.1: sodium borohydride / methanol / -78 °C 2.2: HCl / methanol / Heating 2.3: 6.6 g / sodium borohydride / bis-(2-methoxy-ethyl) ether; methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: CuCl2; KBr; H3PO4 / nitrobenzene / Heating 2.1: sodium borohydride / methanol / -78 °C 2.2: HCl / methanol / Heating 2.3: 6.6 g / sodium borohydride / bis-(2-methoxy-ethyl) ether; methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium bromide; copper dichloride; phosphoric acid / nitrobenzene / 48 h / Reflux 2: aluminum isopropoxide; cyclohexanol / 72 h / Reflux View Scheme

1,8-dibromoanthraquinone (131276-24-9) + p-benzoquinone (106-51-4) → C20H12Br2O2

Conditions	Yield
In isopropyl alcohol Schlenk technique; Inert atmosphere; Reflux;	96%

4-(propionyl)phenylboronic acid pinacol ester (1256359-22-4) + 1,8-dibromoanthraquinone (131276-24-9) → C32H26O2

Conditions	Yield
With palladium diacetate; potassium carbonate; catacxium A In 1,2-dimethoxyethane; water at 85℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere;	95%

Benzophenone imine (1013-88-3) + 1,8-dibromoanthraquinone (131276-24-9) → N1,N8-bis(diphenylmethylene)anthracene-1,8-diamine (1023292-35-4)

Conditions	Yield
With 1,8-bis(diisopropylphosphino)triptycene; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene Buchwald-Hartwig amination;	93%

1,8-dibromoanthraquinone (131276-24-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 8-bromo-anthracene-1-carbaldehyde (1202642-07-6)

Conditions	Yield
Stage #1: 1,8-dibromoanthraquinone With phenyllithium In tetrahydrofuran; dibutyl ether at -78℃; for 1.16667h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; dibutyl ether at -78 - 20℃; for 1h; Inert atmosphere;	92%

3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile + 1,8-dibromoanthraquinone (131276-24-9) → 1,8-bis(4-cyano-2,6-dimethylphenyl)anthracene

Conditions	Yield
With di(1-adamantyl)-n-butylphosphine; palladium diacetate; potassium carbonate In 1,2-dimethoxyethane; water at 85℃; for 20h; Inert atmosphere;	88%

1,8-dibromoanthraquinone (131276-24-9) + N-boc-2-pyrroleboronic acid (135884-31-0) → C32H32N2O4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 18h; Suzuki Coupling; Reflux;	84%

4-(carbazol-9-yl)phenylboronic acid (419536-33-7) + 1,8-dibromoanthraquinone (131276-24-9) → 1,8-bis[4-(9R-carbazole-9-yl)phenyl]anthracene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 14h; Inert atmosphere;	83%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 14h;

piperidine (110-89-4) + 1,8-dibromoanthraquinone (131276-24-9) → 18-dipiperidin-1-ylanthracene

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;	80%

1,8-dibromoanthraquinone (131276-24-9) + trimethylsilylacetylene (1066-54-2) → 1,8-Bis<2-(trimethylsilyl)ethinyl>anthracen (119796-31-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 90℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere;	80%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Inert atmosphere;

(1-Boc-5-propyl-1H-indol-2-yl)boronic acid + 1,8-dibromoanthraquinone (131276-24-9) → C46H48N2O4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 18h; Suzuki Coupling; Reflux;	80%

1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1003846-21-6) + 1,8-dibromoanthraquinone (131276-24-9) → C20H14N4

Conditions	Yield
Stage #1: 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole; 1,8-dibromoanthraquinone With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; butan-1-ol at 110℃; for 72h; Inert atmosphere; Schlenk technique; Stage #2: With hydrogenchloride In water at 20℃; for 6h; Inert atmosphere; Schlenk technique;	78%

1,8-dibromoanthraquinone (131276-24-9) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → 1,8-bis[(diphenylhydroxymethyl)ethynyl]anthracene

Conditions	Yield
With copper(l) iodide; triethylamine; triphenylphosphine; palladium diacetate In toluene at 90℃; for 4h; Substitution;	73%

9-ethynylfluoren-9-ol (13461-74-0) + 1,8-dibromoanthraquinone (131276-24-9) → 1,8-bis[(9-hydroxyfluoren-9-yl)ethynyl]anthracene

Conditions	Yield
With copper(l) iodide; triethylamine; triphenylphosphine; palladium diacetate In toluene at 90℃; for 4h; Substitution;	72%

1,8-dibromoanthraquinone (131276-24-9) + 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline (214360-73-3) → tert-butyl 4,4'-(anthracene-1,8-diyl)bis(4,1-phenylene)dicarbamate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 100℃; for 84h; Suzuki Coupling; Inert atmosphere;	72%

1,8-dibromoanthraquinone (131276-24-9) + (4-(2,2'-dipyridylamino)phenyl)acetylene (467238-88-6) → 1,8-bis[4-(2,2'-dipyridylamino)phenylacetylenyl]anthracene (1381964-36-8)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine for 24h; Reflux; Inert atmosphere;	71%

1,8-dibromoanthraquinone (131276-24-9) + diethyl Fumarate (623-91-6) → C22H20Br2O4

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene Reflux; Schlenk technique; Inert atmosphere;	69%

1,8-dibromoanthraquinone (131276-24-9) + diethyl Fumarate (623-91-6) → C22H20Br2O4

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene Diels-Alder Cycloaddition; Reflux; Inert atmosphere; Schlenk technique;	69%

1,8-dibromoanthraquinone (131276-24-9) + chloro-diphenylphosphine (1079-66-9) → 1,8- bis(diphenylphosphino)anthracene (131276-25-0)

Conditions	Yield
Stage #1: 1,8-dibromoanthraquinone With n-butyllithium In tetrahydrofuran at -78℃; for 1.08333h; Stage #2: chloro-diphenylphosphine In tetrahydrofuran at -78℃; Reflux;	64%

carbon dioxide (124-38-9) + 2-amino-6-methylbenzoic acid (4389-50-8) + 1,8-dibromoanthraquinone (131276-24-9) → 13-methyl-1,8-triptycenedicarboxylic acid

Conditions	Yield
Stage #1: 2-amino-6-methylbenzoic acid; 1,8-dibromoanthraquinone With 1-nitro-3-methylbutane In 1,2-dimethoxyethane at 80℃; Stage #2: With maleic anhydride In Triethylene glycol dimethyl ether Reflux; Stage #3: carbon dioxide Further stages;	64%

1,8-dibromoanthraquinone (131276-24-9) + 2-Amino-4,5-dimethoxybenzoic acid (5653-40-7) → 1,13-dibromo-6,7-dimethoxytriptycene

Conditions	Yield
With isopentyl nitrite In 1,4-dioxane at 100℃; for 1.25h;	63%

4,5-dimethoxybenzyne (54632-05-2) + 1,8-dibromoanthraquinone (131276-24-9) → 1,13-dibromo-6,7-dimethoxytriptycene

Conditions	Yield
In 1,4-dioxane Reflux;	63%

1,8-dibromoanthraquinone (131276-24-9) + trifluoroacetic anhydride (407-25-0) → 1-trifluoroacetylanthracene + 1,8-ditrifluoroacetylanthracene (869061-21-2)

Conditions	Yield
Stage #1: 1,8-dibromoanthraquinone With n-butyllithium In diethyl ether; hexane at 0℃; Stage #2: trifluoroacetic anhydride In diethyl ether; hexane at -78℃;	A 24% B 52%

2-amino-6-methylbenzoic acid (4389-50-8) + 1,8-dibromoanthraquinone (131276-24-9) → C21H14Br2 + C21H14Br2

Conditions	Yield
Stage #1: 2-amino-6-methylbenzoic acid; 1,8-dibromoanthraquinone With 1-nitro-3-methylbutane In 1,2-dimethoxyethane at 80℃; Stage #2: With maleic anhydride In Triethylene glycol dimethyl ether Reflux;	A 15% B 52%

dimesitylfluoroborane (436-59-9) + 1,8-dibromoanthraquinone (131276-24-9) → 1-(dimesitylboryl)anthracene

Conditions	Yield
Stage #1: 1,8-dibromoanthraquinone With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: dimesitylfluoroborane In tetrahydrofuran; hexane at 20℃; for 18h; Inert atmosphere;	44%

dimesitylfluoroborane (436-59-9) + 1,8-dibromoanthraquinone (131276-24-9) → 1,8-bis(dimesitylboryl)anthracene

Conditions	Yield
Stage #1: 1,8-dibromoanthraquinone With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: dimesitylfluoroborane In tetrahydrofuran; hexane at 20℃; for 18h; Inert atmosphere;	40%

2-Amino-5-methylbenzoic acid (2941-78-8) + 1,8-dibromoanthraquinone (131276-24-9) + dimethyl amine (124-40-3) → C23H19Br2N + C23H19Br2N

Conditions

Yield

Stage #1: 2-Amino-5-methylbenzoic acid; 1,8-dibromoanthraquinone With isopentyl nitrite In 1,2-dimethoxyethane Inert atmosphere; Schlenk technique; Glovebox; High pressure; Stage #2: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene Reflux; Inert atmosphere; Schlenk technique; Glovebox; High pressure; Stage #3: dimethyl amine In toluene for 3h; Reflux; Glovebox; Schlenk technique; Inert atmosphere; High pressure;

A 33% B 32%

4-(2,2'-dipyridylamino)phenylbromide + 1,8-dibromoanthraquinone (131276-24-9) + trimethylsilylacetylene (1066-54-2) → 1,8-bis[4-(2,2'-dipyridylamino)phenylacetylenyl]anthracene (1381964-36-8)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine for 48h; Reflux; Inert atmosphere;	20%

1H-imidazole (288-32-4) + 1,8-dibromoanthraquinone (131276-24-9) → 1,8-bisimidazolyl anthracene (1276031-36-7)

Conditions	Yield
With copper(l) iodide; N,N'-diethylethylenediamine; caesium carbonate In N,N-dimethyl-formamide for 48h; Reflux;	17%

Upstream product

• 38313-16-5 1,8-dibromoanthraquinone 
• 82-43-9 1,8-dichloroanthraquinone 
• 869061-20-1 1,8-dibromo-10-anthrone 

Downstream Products

• 100367-09-7 1,8-di-m-tolylanthracene 
• 100367-10-0 1,8-di-o-tolylanthracene 
• 1023292-35-4 N¹,N⁸-bis(diphenylmethylene)anthracene-1,8-diamine 
• 1381964-36-8 1,8-bis[4-(2,2'-dipyridylamino)phenylacetylenyl]anthracene 

Relevant academic research and scientific papers

Enantioselective preparation and structural and conformational analysis of the chiral solvating agent α,α′-bis(trifluoromethyl)-1,8- anthracenedimethanol

The preparation of the enantiomers of α,α′- bis(trifluoromethyl)-1,8-anthracenedimethanol is described, and their conformational behaviour studied. These enantiomers are very active when used as chiral solvating agents in the presence of several compounds.

Synthesis, structure and anion binding properties of 1,8-bis(dimesitylboryl)anthracene and its monoborylated analog

Two boranes, 1-(dimesitylboryl)anthracene (1) and 1,8-bis(dimesitylboryl)anthracene (2), have been synthesized with the spectrophysical properties showing how the inclusion of one or two boron atoms progressively perturbs the π-system of the anthracene backbone. This perturbation is caused by conjugation of the anthracene-π? orbital with the vacant p-orbital on boron. Additionally, both 1 and 2 have a high affinity for fluoride and cyanide anions which are complexed in a 1:1 guest-host ratio. The mono-borane 1 is particularly well-suited for cyanide binding, displaying a binding constant of 3 × 107 in THF. Furthermore, as a result of their unique electronic structures, these boranes display a fluorescence response to fluoride anion characterized by a blue shift in the case of 1 and a red shift in the case of 2.

Selective stepwise Suzuki cross-coupling reaction for the modelling of photosynthetic donor - Acceptor systems

Chemical Equation Presented A Suzuki reaction performed as a selective stepwise substitution of two boryl groups on a diarylporphyrin precursor is reported for straightforward construction of a porphyrin trimer, modeling photosynthetic donor-acceptor systems.

1,8-Bis(diphenylphosphino)anthracene and Metal Complexes

The title compound 4 was synthesized from dipotassium 1,8-anthracenedisulfonate (9) and potassium diphenylphosphide (Ph2PK).On reaction of 4 with nickel(II) chloride and bis(benzonitrile)palladium(II) chloride, cyclometallation of the C-H bond in anthracene 9-position led to the square-planar chelate complexes 11 and 13, respectively.In the case of the palladium complex 13, the cyanometallated structure was proved by X-ray structure analysis.Treatment with aqueous potassium cyanide did not remove nickel from 11, but converted 11 into 12 by substitution of chloride with cyanide, demonstrating the high stability of these cyclometallated chelate complexes.