• Name

  3,6-DIBROMO-PHENANTHRENE

• EINECS
• CAS No. 174735-02-5
• Article Data12
• CAS DataBase
• Density 1.768 g/cm³
• Solubility
• Melting Point 188-191℃
• Formula C₁₄H₈Br₂
• Boiling Point 438.755 °C at 760 mmHg
• Molecular Weight 336.026
• Flash Point 256.192 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 3,6-Dibromophenanthrene;
• PSA 0.00000
• LogP 5.51800

Synthetic route

2765-14-2, 18869-30-2, 23958-29-4, 131899-14-4, 131899-15-5

4,4'-dibromostilbene

174735-02-5

2,9-dibromophenanthrene

Conditions

Conditions	Yield
With tetrahydrofuran; iodine In toluene for 16h; Irradiation;	97%
With iodine In tetrahydrofuran; toluene for 48h; Inert atmosphere; Irradiation;	83%
In cyclohexane Irradiation;

18869-30-2

(E)-4,4'-dibromostilbene

174735-02-5

2,9-dibromophenanthrene

Conditions

Conditions	Yield
With iodine In tetrahydrofuran; toluene for 16h; Irradiation;	97%
With iodine In toluene Irradiation; Inert atmosphere;	80%
With potassium iodide In cyclohexane Schlenk technique; Irradiation; Reflux;	80%
With iodine In benzene Irradiation;	77.2%
With iodine; methyloxirane In cyclohexane for 2h; Photolysis;

860551-67-3

3,6-dibromophenanthrene-9-carboxylic acid

174735-02-5

2,9-dibromophenanthrene

Conditions

Conditions	Yield
With quinoline; copper chromite Heating;	73%

13974-85-1

3,6-Dibrom-9,10-dihydrophenanthren

174735-02-5

2,9-dibromophenanthrene

Conditions

Conditions	Yield
With N-Bromosuccinimide; sodium carbonate

3.6-dibromo-phenanthrene-carboxylic acid-(9)

3.6-dibromo-phenanthrene-carboxylic acid-(9)

174735-02-5

2,9-dibromophenanthrene

Conditions

Conditions	Yield
With quinoline; copper chromite at 210 - 220℃;

1122-91-4

4-bromo-benzaldehyde

174735-02-5

2,9-dibromophenanthrene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 24 h / 20 °C / Inert atmosphere 2: iodine / tetrahydrofuran; toluene / 16 h / Irradiation View Scheme
Multi-step reaction with 3 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 View Scheme

2039-82-9

1-bromo-4-ethenyl-benzene

174735-02-5

2,9-dibromophenanthrene

Conditions

Conditions	Yield
Multi-step reaction with 2 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 View Scheme

773837-37-9

sodium cyanide

174735-02-5

2,9-dibromophenanthrene

C15H8BrN

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 15h;	89%

174735-02-5

2,9-dibromophenanthrene

73183-34-3

bis(pinacol)diborane

1358762-95-4

C26H32B2O4

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 15h; Inert atmosphere;	89%

174735-02-5

2,9-dibromophenanthrene

501-65-5

diphenyl acetylene

13,16-dihydrodiindeno[1,2-b:2′,1′-h]phenanthrene

Conditions

Conditions	Yield
Stage #1: 3,6-dibromophenanthrene; diphenyl acetylene With 1,8-diazabicyclo[5.4.0]undec-7-ene; cesium pivalate; 1,2-bis-(diphenylphosphino)ethane; palladium dichloride In 1,4-dioxane at 130℃; for 24h; Sealed tube; Inert atmosphere; Stage #2: With 18-crown-6 ether; potassium tert-butylate; hydrazine hydrate; potassium hydroxide In 1,4-dioxane at 110℃; for 12h; Inert atmosphere; Sealed tube;	88%

174735-02-5

2,9-dibromophenanthrene

1066-54-2

trimethylsilylacetylene

918778-81-1

3,6-bis-trimethylsilanylethynyl-phenanthrene

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 16h;	86%

622-97-9

1-ethenyl-4-methylbenzene

174735-02-5

2,9-dibromophenanthrene

3-bromo-6-(p-methylstyryl)phenanthrene

Conditions

Conditions	Yield
With sodium acetate; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) In N,N-dimethyl acetamide at 140℃; for 48h; Heck reaction;	84%

637-69-4

4-Methoxystyrene

174735-02-5

2,9-dibromophenanthrene

694502-77-7

3-bromo-6-(p-methoxystyryl)phenanthrene

Conditions

Conditions	Yield
With sodium acetate; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) In N,N-dimethyl acetamide at 140℃; for 48h; Heck reaction;	83%

292638-84-7

styrene

174735-02-5

2,9-dibromophenanthrene

694502-83-5

3,6-distyrylphenanthrene

Conditions

Conditions	Yield
With sodium acetate; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) In N,N-dimethyl acetamide at 140℃; for 48h; Heck reaction;	82%

292638-84-7

styrene

174735-02-5

2,9-dibromophenanthrene

98460-13-0

distyryl-3,6-phenanthrene

Conditions

Conditions	Yield
Stage #1: With 1,3-bis-(diphenylphosphino)propane; palladium diacetate In N,N-dimethyl acetamide at 20℃; Inert atmosphere; Stage #2: styrene; 3,6-dibromophenanthrene With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl acetamide at 100 - 140℃; Mizoroki-Heck reaction; Inert atmosphere;	82%

40243-87-6

3,5-dimethoxystyrene

174735-02-5

2,9-dibromophenanthrene

3-bromo-6-(3,5-dimethoxystyryl)phenanthrene

Conditions

Conditions	Yield
With sodium acetate; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) In N,N-dimethyl acetamide at 140℃; for 48h; Heck reaction;	80%

3435-51-6

4-ethenylbenzonitrile

174735-02-5

2,9-dibromophenanthrene

3-bromo-6-(p-cyanostyryl)phenanthrene

Conditions

Conditions	Yield
With sodium acetate; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) In N,N-dimethyl acetamide at 140℃; for 48h; Heck reaction;	78%

33937-26-7

tetrakis(triethylphosphine)platinum(0)

174735-02-5

2,9-dibromophenanthrene

531500-31-9

2,9-bis[trans-Pt(PEt3)2Br]phenanthrene

Conditions

Conditions	Yield
In toluene under N2 atm. using Schlenk techniques; mixt. of C14H8Br2 and Pt(PEt3)4 in toluene stirred at 45°C for 24 h; solvent removed (vac.); residue washed (MeOH); dried (vac.); elem. anal.;	78%

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%

174735-02-5

2,9-dibromophenanthrene

201802-67-7

4-(diphenylamino)phenyl boronic acid

C50H36N2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In ethanol; water; toluene at 110℃; for 48h; Suzuki Coupling; Inert atmosphere;	76%

174735-02-5

2,9-dibromophenanthrene

86-74-8

9H-carbazole

3,6-di(9H-carbazol-9-yl)phenanthrene

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 100℃; for 48h; Buchwald-Hartwig Coupling; Inert atmosphere;	75%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 90℃; Buchwald-Hartwig Coupling; Inert atmosphere;	75.6%

174735-02-5

2,9-dibromophenanthrene

3,3'-dibenzamidobiphenyl

C40H26N2O2

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 180℃; for 3h; Inert atmosphere;	75%

736987-75-0

4,4,5,5-tetramethyl-2-[(E)-2-(thiophen-3-yl)ethenyl]-1,3,2-dioxaborolane

174735-02-5

2,9-dibromophenanthrene

3,6-bis-((E)-2-(thiophen-3-yl)vinyl)phenanthrene

Conditions

Conditions	Yield
With caesium carbonate; triphenylphosphine; palladium dichloride In tetrahydrofuran; water at 85℃; Sealed tube;	74%

174735-02-5

2,9-dibromophenanthrene

122-39-4

diphenylamine

C38H28N2

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 100℃; for 48h; Buchwald-Hartwig Coupling; Inert atmosphere;	71%

C22H12

174735-02-5

2,9-dibromophenanthrene

C58H30

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 48h; Heck Reaction; Inert atmosphere;	71%

292638-84-7

styrene

174735-02-5

2,9-dibromophenanthrene

A

3-bromo-6-styrylphenanthrene

B

694502-83-5

3,6-distyrylphenanthrene

Conditions

Conditions	Yield
With sodium acetate; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) In N,N-dimethyl acetamide at 140℃; for 48h; Heck reaction;	A 70% B n/a

...Expand

174735-02-5

2,9-dibromophenanthrene

2628-17-3

4-Vinylphenol

3-bromo-6-(p-hydroxystyryl)phenanthrene

Conditions

Conditions	Yield
With sodium acetate; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) In N,N-dimethyl acetamide at 140℃; for 48h; Heck reaction;	70%

174735-02-5

2,9-dibromophenanthrene

C30H38B2O8

5,10-bis(6-bromophenanthren-3-yl)-15,18,19,22-tetraoxapentacyclo-[12.4.4.01,14.02,7.08,13]docosa-2(7),3,5,8(13),9,11-hexaene

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In dimethyl sulfoxide at 80℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	70%

174735-02-5

2,9-dibromophenanthrene

4-(1-(2,4,6-tricyanophenyl)-1H-benzo[d]imidazol-2-yl)benzeneboronic acid

C58H28N10

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide for 0.166667h; Inert atmosphere; Reflux;	65%

161395-82-0

3-(E)-4,4,5,5-tetramethyl-2-(2-(thiophen-2-yl)vinyl)-1,3,2-dioxaborolane

174735-02-5

2,9-dibromophenanthrene

3,6-bis((E)-2-(thiophen-2-yl)vinyl)phenanthrene

Conditions

Conditions	Yield
With caesium carbonate; triphenylphosphine; palladium dichloride In tetrahydrofuran; water at 85℃; Sealed tube;	62%

3,6-Dibromophenanthrene Specification