53622-33-6

Basic information

• Product Name: 2-BroMo-9,10-phenanthrenequinone
• Synonyms: 2-BroMo-9,10-phenanthrenequinone;2-bromo-9,10-phenanthrenedione
• CAS NO: 53622-33-6
• Molecular Formula: C₁₄H₇BrO₂
• Molecular Weight: 287.10818
• EINECS: 1806241-263-5
• Mol File: 53622-33-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 237-238℃ (acetone )
• Appearance: /
• Density: 1.638±0.06 g/cm3 (20 oC 760 Torr), Calc.*
• CAS DataBase Reference: 2-BroMo-9,10-phenanthrenequinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BroMo-9,10-phenanthrenequinone(53622-33-6)
• EPA Substance Registry System: 2-BroMo-9,10-phenanthrenequinone(53622-33-6)

Safety Data

• Hazardous Substances Data: 53622-33-6(Hazardous Substances Data)

Usage

General Description

2-Bromo-9,10-phenanthrenequinone is a chemical compound with the molecular formula C14H7BrO2. It is a brominated derivative of phenanthrenequinone, which is a yellow crystalline solid. 2-Bromo-9,10-phenanthrenequinone is commonly used as a reagent in organic synthesis, particularly in the preparation of various aromatic compounds. It is known for its strong oxidizing properties and is often used as a mild oxidizing and dehydrogenating agent. 2-BroMo-9,10-phenanthrenequinone is also used in the pharmaceutical industry and in research laboratories for its unique chemical properties. However, it is important to handle this chemical with care, as it is toxic and may cause skin and eye irritation.

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

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

Downstream Products

• 84405-44-7 2,7-dibromo-phenanthrene-9,10-dione 
• 3096-56-8 2-bromofluoren-9-one 
• 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 articles and documents

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.

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.