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

3,6-Dibromo-9,10-phenanthrenequinone

 EINECS N/A
CAS No. 53348-05-3 Density 1.911 g/cm3
PSA 34.14000 LogP 4.25760
Solubility N/A Melting Point 291 °C
Formula C14H6Br2O2 Boiling Point 501 °C at 760 mmHg
Molecular Weight 366.008 Flash Point 177.5 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 53348-05-3 (3,6-Dibromo-phenanthrenequinone) Hazard Symbols N/A
Synonyms

3,6-dibromophenanthrene-9,10-dione;

Article Data 67

3,6-Dibromo-9,10-phenanthrenequinone Synthetic route

84-11-7

9,10-phenanthrenequinone

53348-05-3

3,6-dibromo-phenanthrene-9,10-dione

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With bromine; nitrobenzene at 100 - 110℃;
85-01-8

phenanthrene

53348-05-3

3,6-dibromo-phenanthrene-9,10-dione

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

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

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