53622-33-6

Usage

Uses

Used in Organic Synthesis:
2-Bromo-9,10-phenanthrenequinone is used as a reagent in organic synthesis for the preparation of various aromatic compounds. Its strong oxidizing properties make it a valuable component in the synthesis process.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Bromo-9,10-phenanthrenequinone is utilized for its unique chemical properties, contributing to the development of new drugs and medicinal compounds.
Used in Research Laboratories:
2-Bromo-9,10-phenanthrenequinone is employed in research laboratories for studying its chemical properties and potential applications in various scientific fields. Its strong oxidizing nature allows researchers to explore its use in different chemical reactions and processes.

Synthetic route

5-bromo-2-phenylcinnamaldehyde → 2-bromo-phenanthrene-9,10-dione (53622-33-6)

Conditions	Yield
With copper; Selectfluor In acetonitrile at 0℃; for 30h; Temperature;	61%

9,10-phenanthrenequinone (84-11-7) → 2-bromo-phenanthrene-9,10-dione (53622-33-6)

Conditions	Yield
Stage #1: 9,10-phenanthrenequinone With methanesulfonic acid for 0.5h; Stage #2: With N-Bromosuccinimide	44%
With water; bromine im geschlossenen Rohr;
With bromine; nitric acid; silver nitrate; acetic acid

C21H14BrClO → 2-bromo-phenanthrene-9,10-dione (53622-33-6)

Conditions	Yield
With copper; Selectfluor In water; acetonitrile at 25℃; for 12h;	25%

water (7732-18-5) + bromine (7726-95-6) + 9,10-phenanthrenequinone (84-11-7) → 2-bromo-phenanthrene-9,10-dione (53622-33-6)

Conditions	Yield
at 100℃; im geschlossenen Rohr;

diazotized 2-amino-phenanthrene-9,10-dione → 2-bromo-phenanthrene-9,10-dione (53622-33-6)

Conditions	Yield
With hydrogen bromide; copper(I) bromide

1-(2-bromophenyl)-3-(4-chlorophenyl)prop-2-en-1-one + 4-Bromophenylboronic acid (5467-74-3) → 2-bromo-phenanthrene-9,10-dione (53622-33-6)

Conditions	Yield
Multi-step reaction with 2 steps 2: Selectfluor; copper / acetonitrile; water / 12 h / 25 °C View Scheme

2-bromo-phenanthrene-9,10-dione (53622-33-6) → 4-bromo-diphenic acid (54389-66-1)

Conditions	Yield
With oxygen; copper(l) chloride In pyridine for 6h;	100%
With potassium dichromate; sulfuric acid

2-bromo-phenanthrene-9,10-dione (53622-33-6) + methylmagnesium chloride (676-58-4) → C16H15BrO2

Conditions	Yield
Stage #1: 2-bromo-phenanthrene-9,10-dione; methylmagnesium chloride In tetrahydrofuran at 50℃; Stage #2: With acetic acid In tetrahydrofuran Cooling with ice;	90%

2-bromo-phenanthrene-9,10-dione (53622-33-6) + copper(l) cyanide → 9,10-dioxo-9,10-dihydro-phenanthrene-2-carbonitrile

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 180℃; for 24h; Inert atmosphere;	83%

2-bromo-phenanthrene-9,10-dione (53622-33-6) + (5-cyano-2-pyridyl)boronic acid → C20H10N2O2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;	75%

2-bromo-phenanthrene-9,10-dione (53622-33-6) + (4-(10H-phenoxyazine-10-yl)phenyl)boronic acid → C32H19NO3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene Inert atmosphere; Reflux;	64%

4-chloro-5-methylbenzene-1,2-diamine (63155-04-4) + 2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-bromo-11-chloro-12-methyl-dibenzo[a,c]phenazine

Conditions	Yield
With acetic acid

3-hydroxybenzothiophene (520-72-9) + 2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-(2-bromo-10-oxo-10H-[9]phenanthrylidene)-benzo[b]thiophen-3-one

Conditions	Yield
With hydrogenchloride; acetic acid

2,3-diaminoquinoxaline (6640-47-7) + 2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-bromo-dibenzo[f,h]quinoxalino[2,3-b]quinoxaline

2,3-diaminoquinoxaline (6640-47-7) + 2-bromo-phenanthrene-9,10-dione (53622-33-6) + acetic acid (64-19-7) → 2-bromo-dibenzo[f,h]quinoxalino[2,3-b]quinoxaline

naphtho[1,2-b]thiophen-3-ol (116083-05-7) + 2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-(2-bromo-10-oxo-10H-[9]phenanthrylidene)-naphtho[1,2-b]thiophen-3-one

Conditions	Yield
With hydrogenchloride; acetic acid

naphtho[2,3-b]thiophen-3-ol (64289-80-1) + 2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-(2-bromo-10-oxo-10H-[9]phenanthrylidene)-naphtho[2,3-b]thiophen-3-one

Conditions	Yield
With hydrogenchloride; acetic acid

2,3-dihydro-1-thiaphenalen-3-one (18342-85-3) + 2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-(2-bromo-10-oxo-10H-[9]phenanthrylidene)-benzo[de]thiochromen-3-one (123055-85-6)

Conditions	Yield
With hydrogenchloride; acetic acid

2-bromo-phenanthrene-9,10-dione (53622-33-6) + 1,5-diaminoanthraquinone (129-44-2) → 1,5-bis-(9,10-dioxo-9,10-dihydro-[2]phenanthrylamino)-anthraquinone

2-bromo-phenanthrene-9,10-dione (53622-33-6) + acenaphthene-4,5-diamine (7473-20-3) → 2-bromo-11,12-dihydro-dibenz[h,j]indeno[7,1-ab]phenazine

2-bromo-phenanthrene-9,10-dione (53622-33-6) + o-phenylenediamine hydrochloride (39145-59-0) → 2-bromo-dibenzo[a,c]phenazine (113012-13-8)

Conditions	Yield
With ethanol

2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-bromofluoren-9-one (3096-56-8)

Conditions	Yield
With potassium hydroxide

2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-bromofluoren-9-one (3096-56-8) + 2-bromo-9-hydroxy-fluorene-9-carboxylic acid

Conditions	Yield
With potassium hydroxide at 80 - 90℃;

2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2,7-dibromo-phenanthrene-9,10-dione (84405-44-7)

Conditions	Yield
With water; bromine at 150 - 160℃; im geschlossenen Rohr;

2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-bromo-phenanthrene-9,10-dione monooxime

Conditions	Yield
With ethanol; hydroxylamine hydrochloride

2-bromo-phenanthrene-9,10-dione (53622-33-6) → 9,10-diacetoxy-2-bromo-phenanthrene

Conditions	Yield
With phenylhydrazine; benzene Behandeln mit Essigsaeureanhydrid;

2-bromo-phenanthrene-9,10-dione (53622-33-6) → 9,10-bis-benzoyloxy-2-bromo-phenanthrene

Conditions	Yield
With alkaline Na2S2O4 Behandeln der entstandenen Loesung mit Benzoylchlorid;

2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2-bromo-dibenzo[a,c]quinoxalino[2,3-i]phenazine

2-bromo-phenanthrene-9,10-dione (53622-33-6) → 2,11-dibromo-tetrabenzo[a,c,h,j]phenazine

Conditions	Yield
With ammonia at 130 - 140℃; im Rohr;

2-bromo-phenanthrene-9,10-dione (53622-33-6) + 3-nitro-benzaldehyde (99-61-6) → 10-bromo-2-(3-nitro-phenyl)-1(3)H-phenanthro[9,10-d]imidazole

2-bromo-phenanthrene-9,10-dione (53622-33-6) + 1-amino-9,10-anthracenedione (82-45-1) → 1-(9,10-dioxo-9,10-dihydro-[2]phenanthrylamino)-anthraquinone (75534-82-6)

Conditions	Yield
With sodium carbonate; nitrobenzene; copper(II) oxide

2-bromo-phenanthrene-9,10-dione (53622-33-6) + 1,2-diamino-benzene (95-54-5) → 2-bromo-dibenzo[a,c]phenazine (113012-13-8)

Conditions	Yield
With acetic acid

Upstream product

• 7732-18-5 water 
• 7726-95-6 bromine 
• 84-11-7 9,10-phenanthrenequinone 
• 5467-74-3 4-Bromophenylboronic acid 

Downstream Products

• 3096-56-8 2-bromofluoren-9-one 
• 84405-44-7 2,7-dibromo-phenanthrene-9,10-dione 
• 23842-56-0 2-bromo-7-nitro-fluoren-9-one oxime 
• 58557-62-3 2-bromo-7-nitro-9H-fluoren-9-one 
• 23842-57-1 2-bromo-fluoren-9-one oxime 

Relevant academic research and scientific papers

Copper(0)/Selectfluor System-Promoted Oxidative Carbon-Carbon Bond Cleavage/Annulation of o-Aryl Chalcones: An Unexpected Synthesis of 9,10-Phenanthraquinone Derivatives

A general and efficient protocol for the synthesis of 9,10-phenanthraquinone derivatives has been successfully developed involving a copper(0)/Selectfluor system-promoted oxidative carbon-carbon bond cleavage/annulation of o-aryl chalcones. A variety of substituted 9,10-phenanthraquinones were synthesized in moderate to good yields under mild reaction conditions.

Synthesis method of 9,10-phenanthrenequinone compound

The invention provides a preparation method of a 9,10-phenanthrenequinone compound. The preparation method comprises: reacting a raw material, namely 2-aryl cinnamaldehyde as shown in the formula I inan organic solvent at the temperature of 0-50 DEG C for 12-36h under the actions of a copper catalyst and an oxidant, and separating and purifying the obtained reaction liquid to prepare the 9,10-phenanthrenequinone compound as shown in the formula II. The preparation method is simple and available in raw material, mild in reaction condition, capable of avoiding using an expensive and poisonouscatalyst or ligand, safe and environment-friendly, high in atom economy and simple in operation, and a novel method is provided for synthesizing 9,10-phenanthrenequinone containing various substituentgroups.

Compositions with triarylamine derivatives and oled device containing the same

The present disclosure provides a composition. In an embodiment, a composition is provided and comprises a Compound 1 shown below: For Compound 1, R1 through R24 are the same or different. R1 through R24 each is independently selected from the group consisting of hydrogen, unsubstituted hydrocarbyl, substituted hydrocarbyl, cyano, alkoxy, aryloxy, and NR'2. R' is hydrogen or hydrocarbyl; wherein two or more of adjacent R1 to R24 may optionally form one or more ring structures. The Component Z is selected from the group consisting Group Z-1, Group Z-2, Group Z-3, Group Z-4, Group Z-5, Group Z-6 and Group Z-7 shown below: For Compound 1, one or more hydrogen atoms may optionally be substituted with deuterium.

Cd45 inhibitors

Substituted phenanthrene-9,10-diones in accord with structural diagram I, 1compositions thereof and methods for the use thereof, for the treatment of T cell mediated conditions such as autoimmune diseases and organ graft rejection. In compounds of the invention, R1 at each occurrence is independently selected from hydrogen, halogen, NH-tosyl, N-di-tosyl, NH2, NO2, NH—CO—R2, CO—NH—R2, Ar, (CH2)nCH(COOH)R3 COR3 and NHCOCH2CH(COOH)NHR4, where R2, R3 and R4 are a selected from a variety of substituted or unsubstituted alkyl and aryl groupstand oligopeptides.