3,6-Dibromo-9,10-phenanthrenequinone supplier

Name
3,6-Dibromo-phenanthrenequinone
EINECS
CAS No. 53348-05-3
Article Data67
CAS DataBase
Density 1.911 g/cm³
Solubility
Melting Point 291 °C
Formula C₁₄H₆Br₂O₂
Boiling Point 501 °C at 760 mmHg
Molecular Weight 366.008
Flash Point 177.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3,6-dibromophenanthrene-9,10-dione;
PSA 34.14000
LogP 4.25760

Synthetic route

: 84-11-7
9,10-phenanthrenequinone

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

Conditions

Conditions	Yield
With bromine; dibenzoyl peroxide In nitrobenzene at 110℃; for 16h;	95%
With bromine; dibenzoyl peroxide In nitrobenzene at 60℃; UV-irradiation;	92%
With bromine; dibenzoyl peroxide In nitrobenzene at 120℃; for 1h;	91%

: 174735-02-5
2,9-dibromophenanthrene

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

Conditions

Conditions	Yield
With chromium(VI) oxide; acetic acid for 1h; Reflux; Inert atmosphere;	78%

3-bromo-phenanthrene-quinone-(9.10): 3-bromo-phenanthrene-quinone-(9.10)

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

Conditions

Conditions	Yield
With bromine; nitrobenzene at 100 - 110℃;

: 85-01-8
phenanthrene

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium dichromate; sulfuric acid / water / 85 - 115 °C 2: bromine; dibenzoyl peroxide / nitrobenzene / 1 h / 75 °C / Irradiation View Scheme

: 2039-82-9
1-bromo-4-ethenyl-benzene

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium acetate; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) / N,N-dimethyl acetamide / 48 h / 100 - 140 °C / Schlenk technique; Inert atmosphere 2: iodine / toluene / Irradiation; Inert atmosphere 3: chromium(VI) oxide; acetic acid / 1 h / Reflux; Inert atmosphere View Scheme

: 1122-91-4
4-bromo-benzaldehyde

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / 1,2-dimethoxyethane / 1 h / Inert atmosphere 1.2: 24 h / 80 °C / Inert atmosphere 2.1: sodium acetate; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) / N,N-dimethyl acetamide / 48 h / 100 - 140 °C / Schlenk technique; Inert atmosphere 3.1: iodine / toluene / Irradiation; Inert atmosphere 4.1: chromium(VI) oxide; acetic acid / 1 h / Reflux; Inert atmosphere View Scheme

Yield

Multi-step reaction with 4 steps
1.1: potassium carbonate / 1,2-dimethoxyethane / 1 h / Inert atmosphere
1.2: 24 h / 80 °C / Inert atmosphere
2.1: sodium acetate; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) / N,N-dimethyl acetamide / 48 h / 100 - 140 °C / Schlenk technique; Inert atmosphere
3.1: iodine / toluene / Irradiation; Inert atmosphere
4.1: chromium(VI) oxide; acetic acid / 1 h / Reflux; Inert atmosphere
View Scheme

: 18869-30-2
(E)-4,4'-dibromostilbene

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: iodine / toluene / Irradiation; Inert atmosphere 2: chromium(VI) oxide; acetic acid / 1 h / Reflux; Inert atmosphere View Scheme

: 3,6-dibromophenanthrene-9,10-diamine chloride

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 3,6,12,15-tetrabromo-tetrabenzophenazine

Conditions

Conditions	Yield
With acetic acid; triethylamine In ethanol at 100 - 130℃; for 6h; Inert atmosphere;	100%

: 3-phenyl-1-(1H-pyrazol-1-yl)but-3-en-1-one

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

A: (R)-3,6-dibromo-4′-phenyl-10H-spiro[phenanthrene-9,2′-pyran]-6′,10(3′H)-dione

B: (S)-3,6-dibromo-4′-phenyl-10H-spiro[phenanthrene-9,2′-pyran]-6′,10(3′H)-dione

Conditions

Conditions	Yield
With C26H26F5N3S In dichloromethane at 25℃; for 6h; enantioselective reaction;	A 99% B n/a

...Expand

: 77-78-1
dimethyl sulfate

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 888728-75-4
3,6-dibromo-9,10-bis-methoxyphenanthrene

Conditions

Conditions	Yield
Stage #1: 3,6-dibromo-phenanthrene-9,10-dione With sodium dithionite; tetrabutylammomium bromide In tetrahydrofuran; water Inert atmosphere; Stage #2: dimethyl sulfate With sodium hydroxide In tetrahydrofuran; water Cooling with ice; Inert atmosphere;	98%
Stage #1: 3,6-dibromo-phenanthrene-9,10-dione With sodium dithionite; tetrabutylammomium bromide In tetrahydrofuran; water for 0.0833333h; Stage #2: dimethyl sulfate With sodium hydroxide In tetrahydrofuran; water for 0.25h; Cooling with ice;	92%
With sodium hydroxide; sodium dithionite; tetrabutylammomium bromide In tetrahydrofuran; water for 0.25h;	90%

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 619-05-6
3,4-diaminobenzoic acid

: 1616777-39-9
2,7-dibromodibenzo[a,c]phenazine-11-carboxylic acid

Conditions

Conditions	Yield
With acetic acid In ethanol for 2h; Reflux;	98%

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 129365-93-1
4,5-diaminophthalonitrile

: 3,6-dibromodibenzo[a,c]phenazine-11,12-dicarbonitrile

Conditions

Conditions	Yield
With acetic acid In ethanol; 1,2-dichloro-benzene for 48h; Sealed tube; Reflux;	98%
With acetic acid for 8h; Inert atmosphere; Schlenk technique; Reflux;	92%

: 95-54-5
1,2-diamino-benzene

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 112865-07-3
3,6-dibromodibenzo[a,c]phenazine

Conditions

Conditions	Yield
With acetic acid In methanol for 3h; Reflux;	97%
With acetic acid In ethanol for 3h; Reflux; Inert atmosphere;	96%
With acetic acid In ethanol at 80℃; for 4h;	91%
With acetic acid

: 67713-23-9
2,6-dibromobenzaldehyde

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 892550-50-4
6,9-dibromo-2-(2,6-dibromophenyl)-1H-phenanthro[9,10-d]imidazole

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In water; toluene for 22h; Heating / reflux;	97%
With ammonium acetate; acetic acid for 16h; Heating / reflux;	97%
With ammonium acetate In acetic acid for 16h; Heating / reflux;	97%

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 49764-63-8
4,5-dibromo-1,2-diaminobenzene

: 3,6,11,12-tetrabromodibenzo[a,c]phenazine

Conditions

Conditions	Yield
In ethanol for 10h; Reflux; Inert atmosphere;	96%
With acetic acid at 110℃; for 6h; Temperature;	90%
With acetic acid at 110℃; for 3h; Inert atmosphere;

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 952054-63-6
2,9-dibromo-5,6-dihydroxyphenanthrene

Conditions

Conditions	Yield
With sodium dithionite In tetrahydrofuran; water at 20℃; for 6h; Inert atmosphere;	95%
With sodium dithionite In N,N-dimethyl-formamide for 0.25h;
With sodium dithionite; tetrabutylammomium bromide In tetrahydrofuran; water for 0.5h;
With sodium dithionite In tetrahydrofuran; water at 20℃; for 6h;	1.4 g
With sodium dithionite In tetrahydrofuran; water at 20℃; for 6h; Inert atmosphere;

: 69272-50-0
1,2-diamine-3,6-dibromobenzene

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 3,6,10,13-tetrabromophenanthridine

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 100℃; for 4h;	95%
With sodium hydroxide In ethanol at 100℃; for 4h;	95%

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 1575-37-7
4-Bromo-benzene-1,2-diamine

: 3,6,11‑tribromodibenzo[a,c]phenazine

Conditions

Conditions	Yield
In ethanol at 100℃; for 2h; Inert atmosphere;	95%
With acetic acid at 110℃; for 6h; Temperature;	95%
With acetic acid for 3h; Reflux;	93%

: 623-27-8
terephthalaldehyde,

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 4-(6,9-dibromo-1H-phenanthro[9,10-d]imidazol-2-yl)benzaldehyde

Conditions

Conditions	Yield
With ammonium acetate; acetic acid for 8h; Reflux; Inert atmosphere;	95%

: 76179-40-3
2-amino-4,5-difluoroaniline

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 3,6-dibromo-11,12-difluorodibenzo[a,c]phenazine

Conditions

Conditions	Yield
In ethanol at 80℃; for 2h; Inert atmosphere;	95%

: 39070-63-8
4-benzoylbenzene-1,2-diamine

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: (3,6-dibromodibenzo[a,c]phenazin-11-yl)(phenyl)methanone

Conditions

Conditions	Yield
With acetic acid for 3h; Reflux;	93%
With acetic acid for 8h; Reflux;	83%

: 78-90-0, 10424-38-1
1,2-diaminopropan

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: C17H10Br2N2

Conditions

Conditions	Yield
Stage #1: 1,2-diaminopropan; 3,6-dibromo-phenanthrene-9,10-dione In toluene for 24h; Reflux; Stage #2: With manganese(IV) oxide In toluene at 93℃; for 0.75h; Solvent; Inert atmosphere;	92%

: 107-21-1
ethylene glycol

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 887127-61-9
3,6-dibromophenanthren-9,10-di(ethyleneglycol)ketal

Conditions

Conditions	Yield
With 10-camphorsufonic acid In methanol at 120℃; for 3h; Inert atmosphere;	91%
With toluene-4-sulfonic acid In toluene at 140℃; for 14h;	75%
With camphor-10-sulfonic acid In methanol at 120 - 130℃; for 24h;	60%

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 408359-97-7
[4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenyl]diphenylamine

: 1415100-79-6
3,6-bis[4-(diphenylamino)phenyl]-9,10-phenanthrenequinone

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 60 - 85℃; for 16h; Inert atmosphere;	91%

: 37466-90-3
ethyl 3,4-diaminobenzoate

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 1616777-40-2
ethyl 2,7-dibromodibenzo[a,c]phenazine-11-carboxylate

Conditions

Conditions	Yield
With acetic acid In ethanol for 2h; Reflux;	91%

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 73183-34-3
bis(pinacol)diborane

: C26H30B2O6

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 150℃; for 10h; Inert atmosphere;	90%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane for 3h; Inert atmosphere; Reflux;	86%

: 939-97-9
4-tert-Butylbenzaldehyde

: 62-53-3
aniline

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: C31H24Br2N2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid at 120℃; for 4h; Inert atmosphere;	90%

...Expand

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 3,6‐dibromo‐2‐iodophenanthrene‐9,10‐dione

Conditions

Conditions	Yield
With N-iodo-succinimide; sulfuric acid; trifluoroacetic acid at 50℃; for 72h; Inert atmosphere; Schlenk technique; chemoselective reaction;	90%

: 771-97-1
2,3-Diaminonaphthalene

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 3,6-dibromotribenzo[a,c,i]phenazine

Conditions

Conditions	Yield
With acetic acid Reflux;	89%
With acetic acid for 3h; Reflux;

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 216312-73-1
3,6-dibromofluoren-9-one

Conditions

Conditions	Yield
With potassium permanganate; potassium hydroxide In water at 130℃; for 1h; Inert atmosphere;	88%
Stage #1: 3,6-dibromo-phenanthrene-9,10-dione With potassium hydroxide In water at 130℃; for 0.5h; Stage #2: With potassium permanganate In water at 130℃; for 3h;	72%
Stage #1: 3,6-dibromo-phenanthrene-9,10-dione With potassium hydroxide In water at 130℃; for 0.5h; Stage #2: With potassium permanganate at 130℃; for 78h;	72%

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 302554-81-0
9,9-dioctylfluorene-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

: 1174669-48-7
3,6-bis(9',9'-dioctylfluoren-2'-yl)-9,10-phenanthraquinone

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water Suzuki coupling; Reflux;	88%

: 111-25-1
1-bromo-hexane

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 1029694-69-6
3,6-dibromo-9,10-bis(hexyloxy)phenanthrene

Conditions

Conditions	Yield
Stage #1: 3,6-dibromo-phenanthrene-9,10-dione With sodium dithionite; tetrabutylammomium bromide In tetrahydrofuran; water at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-bromo-hexane With potassium hydroxide In tetrahydrofuran; water at 80℃; for 3h; Inert atmosphere;	88%
Stage #1: 3,6-dibromo-phenanthrene-9,10-dione With sodium dithionite In N,N-dimethyl-formamide for 0.25h; Inert atmosphere; Stage #2: 1-bromo-hexane With tetrabutylammomium bromide; potassium hydroxide In N,N-dimethyl-formamide at 60℃; for 60h; Inert atmosphere;	42%
Stage #1: 3,6-dibromo-phenanthrene-9,10-dione With sodium dithionite; tetrabutylammomium bromide In tetrahydrofuran; water Inert atmosphere; Stage #2: 1-bromo-hexane With potassium hydroxide In tetrahydrofuran; water at 20℃; for 48h; Inert atmosphere;
Stage #1: 3,6-dibromo-phenanthrene-9,10-dione With sodium dithionite; tetrabutylammomium bromide In tetrahydrofuran; water for 1h; Stage #2: 1-bromo-hexane With potassium hydroxide In tetrahydrofuran; water at 25℃; for 48h;

: 129012-04-0
2,3-Diamino-6-bromopyridine

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 3,6,11-tribromodibenzo[f,h]pyrido[2,3-b]quinoxaline

Conditions

Conditions	Yield
In ethanol at 90℃; Inert atmosphere;	88%

: 1374605-89-6
tert-butyl 2-oxo-3-(propan-2-ylidene)indoline-1-carboxylate

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: tert-butyl (2-(3,6-dibromo-4′-methyl-6′,10-dioxo-3′,6′-dihydro-10H-spiro[phenanthrene-9,2′-pyran]-5′-yl)phenyl)carbamate

Conditions

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In dichloromethane at 20℃; for 24h; enantioselective reaction;	88%

: 387-45-1
2-chloro-6-fluorobenzaldehyde

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 892550-42-4
6,9-dibromo-2-(2-chloro-6-fluorophenyl)-1H-phenanthro[9,10-d]imidazole

Conditions

Conditions	Yield
With ammonium bicarbonate In acetic acid at 130℃;	87%
With ammonium bicarbonate; acetic acid In water; toluene at 20 - 130℃; Heating / reflux;	80%
With ammonium bicarbonate; acetic acid at 130℃; Heating / reflux;	80%
With ammonium bicarbonate In acetic acid at 130℃;	80%

: 623-27-8
terephthalaldehyde,

: 104-94-9
4-methoxy-aniline

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 4-(6,9-dibromo-1-(4-methoxyphenyl)-1H-phenanthro[9,10-d]imidazol-2-yl)benzaldehyde

Conditions

Conditions	Yield
With ammonium acetate; acetic acid for 18h; Reflux; Inert atmosphere;	87%

...Expand

3,6-Dibromo-9,10-phenanthrenequinone Specification

The 3,6-Dibromo-9,10-phenanthrenequinone is an organic compound with the formula C₁₄H₆Br₂O₂. With the CAS registry number 53348-05-3, the IUPAC name of this chemical is 3,6-dibromophenanthrene-9,10-dione.

Physical properties about 3,6-Dibromo-9,10-phenanthrenequinone are: (1)ACD/LogP: 4.67; (2)#H bond acceptors: 2 ; (3)Polar Surface Area: 34.14 Å²; (4)Index of Refraction: 1.7; (5)Molar Refractivity: 74.04 cm³; (6)Molar Volume: 191.4 cm³; (7)Polarizability: 29.35×10^-24cm³; (8)Surface Tension: 61.8 dyne/cm; (9)Density: 1.911 g/cm³; (10)Flash Point: 177.5 °C; (11)Enthalpy of Vaporization: 76.97 kJ/mol; (12)Boiling Point: 501 °C at 760 mmHg; (13)Vapour Pressure: 3.62E-10 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Brc3cc2c1c(ccc(Br)c1)C(=O)C(=O)c2cc3
(2)InChI: InChI=1/C14H6Br2O2/c15-7-1-3-9-11(5-7)12-6-8(16)2-4-10(12)14(18)13(9)17/h1-6H
(3)InChIKey: WPEJBJRFPBMVGJ-UHFFFAOYAL
(4)Std. InChI: InChI=1S/C14H6Br2O2/c15-7-1-3-9-11(5-7)12-6-8(16)2-4-10(12)14(18)13(9)17/h1-6H
(5)Std. InChIKey: WPEJBJRFPBMVGJ-UHFFFAOYSA-N

Product Name

3,6-Dibromo-phenanthrenequinone

Synthetic route

3,6-Dibromo-9,10-phenanthrenequinone Specification

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