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573-17-1

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573-17-1 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 573-17-1 differently. You can refer to the following data:
1. light yellow powder
2. Soluble in toluene, and chloroform (50 mg/ml)

Uses

9-Bromophenanthrene is used as halogenated building block. Isotope labelled 9-Bromophenanthrene (B687200), a halogenated polycyclic aromatic hydrocarbon that has been seen to have a room temperature phosphorescence that can be induced by β-cyclodextrin (β-CD) in the presence of cyclohexane; however, trace Fe(III) causes a decrease of the RTP emission.

Preparation

9-Bromophenanthrene (90-94%) is produced by adding bromine to a refluxing solution of phenanthrene in carbon tetrachloride. This is the starting-point of 9-substituted phenanthrenes, e.g, when heated with cuprous cyanide at 260℃, 9-bromophenanthrene forms the corresponding cyano-compound; this may be hydrolysed to phenanthrene-9-carboxylic acid. Phenanthrene undergoes the Friedel-Crafts reaction mainly in the 3-, and to a small extent, in the 2-position. It is chloromethylated in the 9-position. When nitrated, phenanthrene gives a mixture of three mononitro-derivatives, the 3-isomer predominating. Sulphonation of phenanthrene gives a mixture of 1-, 2-, 3- and 9-phenanthrenesulphonic acids, and the ratio of these isomers depends on the temperature.

Check Digit Verification of cas no

The CAS Registry Mumber 573-17-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,7 and 3 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 573-17:
(5*5)+(4*7)+(3*3)+(2*1)+(1*7)=71
71 % 10 = 1
So 573-17-1 is a valid CAS Registry Number.
InChI:InChI=1/C14H9Br/c15-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9H

573-17-1 Well-known Company Product Price

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  • TCI America

  • (B0838)  9-Bromophenanthrene  >98.0%(GC)

  • 573-17-1

  • 25g

  • 650.00CNY

  • Detail
  • Alfa Aesar

  • (L09033)  9-Bromophenanthrene, 98%   

  • 573-17-1

  • 5g

  • 205.0CNY

  • Detail
  • Alfa Aesar

  • (L09033)  9-Bromophenanthrene, 98%   

  • 573-17-1

  • 25g

  • 539.0CNY

  • Detail

573-17-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 9-Bromophenanthrene

1.2 Other means of identification

Product number -
Other names Phenanthrene, 9-bromo-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:573-17-1 SDS

573-17-1Synthetic route

phenanthrene
85-01-8

phenanthrene

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Conditions
ConditionsYield
With aluminum oxide; copper(ll) bromide In chlorobenzene at 80℃; for 2h;97%
With aluminum oxide; copper(ll) bromide In tetrachloromethane at 80℃; for 2h;95%
With bromine In chloroform for 17h; Reflux; Inert atmosphere;93%
phenanthrene
85-01-8

phenanthrene

A

9-bromophenanthrene
573-17-1

9-bromophenanthrene

9,10-dibromo-9,10-dihydrophenanthrene

9,10-dibromo-9,10-dihydrophenanthrene

Conditions
ConditionsYield
With bromine In Hexadecane for 480h; Cooling;A 32%
B 42%
With tri(decyl)(methyl)phosphonium tribromide; bromine In Hexadecane; tetradecafluorohexane for 480h;A 36%
B 7%
9-iodo-phenanthrene
17024-12-3

9-iodo-phenanthrene

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; for 60h;18%
tetrachloromethane
56-23-5

tetrachloromethane

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

phenanthrene
85-01-8

phenanthrene

9-bromophenanthrene
573-17-1

9-bromophenanthrene

9,10-dibromo-9,10-dihydro-phenanthrene
17533-18-5

9,10-dibromo-9,10-dihydro-phenanthrene

silver(I) acetate
563-63-3

silver(I) acetate

acetic acid
64-19-7

acetic acid

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Phenanthrene-9-carbonyl bromide

Phenanthrene-9-carbonyl bromide

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Conditions
ConditionsYield
With RhCl(PPh3)3 at 300℃;
phenanthrene dibromide

phenanthrene dibromide

9-bromophenanthrene
573-17-1

9-bromophenanthrene

α-tetrahydrophenanthrene

α-tetrahydrophenanthrene

A

9-bromophenanthrene
573-17-1

9-bromophenanthrene

B

2,7-dibromophenanthrene
62325-30-8

2,7-dibromophenanthrene

Conditions
ConditionsYield
With chloroform; bromine
tetrachloromethane
56-23-5

tetrachloromethane

phenanthrene
85-01-8

phenanthrene

bromine (2 or 3 atoms)

bromine (2 or 3 atoms)

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Conditions
ConditionsYield
at 0 - 76℃;
chloroform
67-66-3

chloroform

phenanthrene
85-01-8

phenanthrene

bromine (2 or 3 atoms)

bromine (2 or 3 atoms)

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Conditions
ConditionsYield
at 0 - 76℃;
phenanthrene
85-01-8

phenanthrene

bromine
7726-95-6

bromine

A

9-bromophenanthrene
573-17-1

9-bromophenanthrene

B

9,10-dibromo-9,10-dihydro-phenanthrene
17533-18-5

9,10-dibromo-9,10-dihydro-phenanthrene

C

1.9-,2.7-,2(?).10-,3.9-or 4.10-dibromo-phenanthrene

1.9-,2.7-,2(?).10-,3.9-or 4.10-dibromo-phenanthrene

9,10-dibromo-9,10-dihydro-phenanthrene
17533-18-5

9,10-dibromo-9,10-dihydro-phenanthrene

A

9-bromophenanthrene
573-17-1

9-bromophenanthrene

B

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

Conditions
ConditionsYield
beim Erhitzen fuer sich;
9,10-dibromo-9,10-dihydro-phenanthrene
17533-18-5

9,10-dibromo-9,10-dihydro-phenanthrene

water
7732-18-5

water

A

9-bromophenanthrene
573-17-1

9-bromophenanthrene

B

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

Conditions
ConditionsYield
im geschlossenen Rohr;
9,10-dihydrophenanthrene
776-35-2

9,10-dihydrophenanthrene

A

9-bromophenanthrene
573-17-1

9-bromophenanthrene

B

phenanthrene
85-01-8

phenanthrene

Conditions
ConditionsYield
With N-Bromosuccinimide; biphenyl In benzene at 20℃; for 2h; Product distribution; Further Variations:; time dependence; Irradiation;A 5.5 % Chromat.
B 94.5 % Chromat.
phenanthrene
85-01-8

phenanthrene

A

9-bromophenanthrene
573-17-1

9-bromophenanthrene

B

9-chlorophenanthrene
947-72-8

9-chlorophenanthrene

Conditions
ConditionsYield
With bromine at 100℃; for 4h; Reflux; Ionic liquid;
naphthalene
91-20-3

naphthalene

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
2: sodium amide; potassium tert-butylate / tetrahydrofuran / 15 h / 50 °C / Inert atmosphere
3: perrhenic acid anhydride; triphenyl phosphite / toluene / 80 °C / Inert atmosphere
4: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
View Scheme
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium amide; potassium tert-butylate / tetrahydrofuran / 15 h / 50 °C / Inert atmosphere
2: perrhenic acid anhydride; triphenyl phosphite / toluene / 80 °C / Inert atmosphere
3: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
View Scheme
1,4-dihydro-1,4-epoxyphenanthrene
83164-98-1

1,4-dihydro-1,4-epoxyphenanthrene

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: perrhenic acid anhydride; triphenyl phosphite / toluene / 80 °C / Inert atmosphere
2: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
View Scheme
benzene
71-43-2

benzene

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 24 h / 80 °C / Inert atmosphere
2: sodium amide; potassium tert-butylate / tetrahydrofuran / 15 h / 50 °C / Inert atmosphere
3: ammonium perrhenate; triphenyl phosphite / toluene / 18 h / 80 °C / Inert atmosphere
4: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
5: sodium amide; potassium tert-butylate / tetrahydrofuran / 15 h / 50 °C / Inert atmosphere
6: perrhenic acid anhydride; triphenyl phosphite / toluene / 80 °C / Inert atmosphere
7: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
View Scheme
bromobenzene
108-86-1

bromobenzene

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium amide; potassium tert-butylate / tetrahydrofuran / 15 h / 50 °C / Inert atmosphere
2: ammonium perrhenate; triphenyl phosphite / toluene / 18 h / 80 °C / Inert atmosphere
3: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
4: sodium amide; potassium tert-butylate / tetrahydrofuran / 15 h / 50 °C / Inert atmosphere
5: perrhenic acid anhydride; triphenyl phosphite / toluene / 80 °C / Inert atmosphere
6: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
View Scheme
1,4-dihydronaphthalene-1,4-epoxide
573-57-9

1,4-dihydronaphthalene-1,4-epoxide

9-bromophenanthrene
573-17-1

9-bromophenanthrene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: ammonium perrhenate; triphenyl phosphite / toluene / 18 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
3: sodium amide; potassium tert-butylate / tetrahydrofuran / 15 h / 50 °C / Inert atmosphere
4: perrhenic acid anhydride; triphenyl phosphite / toluene / 80 °C / Inert atmosphere
5: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
View Scheme
9,10-dihydrodibenzazepine
494-19-9

9,10-dihydrodibenzazepine

9-bromophenanthrene
573-17-1

9-bromophenanthrene

N-(9-phenanthryl)iminodibenzyl

N-(9-phenanthryl)iminodibenzyl

Conditions
ConditionsYield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;100%
9-bromophenanthrene
573-17-1

9-bromophenanthrene

2,6-dimethylbenzene boronic acid
100379-00-8

2,6-dimethylbenzene boronic acid

9-(2,6-dimethyl-phenyl)-phenanthrene

9-(2,6-dimethyl-phenyl)-phenanthrene

Conditions
ConditionsYield
With potassium phosphate; N,N-diisopropyl 2-dicyclohexylphosphino-4-phenylbenzamide; tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl-formamide at 110℃; for 9h; Suzuki cross-coupling;99.5%
9-bromophenanthrene
573-17-1

9-bromophenanthrene

phenanthrene
85-01-8

phenanthrene

Conditions
ConditionsYield
With potassium fluoride In tetrahydrofuran; water at 80℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Sealed tube; Inert atmosphere;99%
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 1.5h; Reagent/catalyst; Solvent; Temperature;99%
With 2-H-1,3-di-tert-butyl-1,3,2-diazaphosphorinane; 2,2'-azobis(isobutyronitrile) In toluene at 90℃; for 5h;99%
9-bromophenanthrene
573-17-1

9-bromophenanthrene

9-deuteriophenanthrene
4819-99-2

9-deuteriophenanthrene

Conditions
ConditionsYield
With 4-methyl-morpholine; tetrahydroxydiborane(4); 5%-palladium/activated carbon; DMAP-d6 In 1,2-dichloro-ethane at 50℃; for 3.5h; Solvent; Reagent/catalyst;99%
With potassium phosphate; d(4)-methanol; palladium diacetate; catacxium A In toluene at 80℃; for 16h;94%
With 2,2'-azobis(isobutyronitrile); C11H24(2)HN2P In (2)H8-toluene at 90℃; for 5h; Mechanism;90%
With n-butyllithium; water-d2 1.) ehter, hexane, 2.) ether, hexane, from 0 to 5 deg C, 1 h; Yield given. Multistep reaction;
With deuteromethanol; tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 32h; Reagent/catalyst; Electrolysis; Green chemistry;96 %Spectr.
9-bromophenanthrene
573-17-1

9-bromophenanthrene

dimethyl sulfate
77-78-1

dimethyl sulfate

9-methylphenanthrene
883-20-5

9-methylphenanthrene

Conditions
ConditionsYield
Stage #1: 9-bromophenanthrene With n-butyllithium In diethyl ether at 20℃; for 1h;
Stage #2: dimethyl sulfate In diethyl ether for 5h; Heating; Further stages.;
99%
Stage #1: 9-bromophenanthrene With n-butyllithium In diethyl ether; hexane at 20℃; Inert atmosphere; Cooling with ice;
Stage #2: dimethyl sulfate In diethyl ether; hexane at 0℃; Inert atmosphere; Reflux;
99%
Stage #1: 9-bromophenanthrene With n-butyllithium In diethyl ether; hexane at 0 - 23℃; for 0.333333h; Inert atmosphere;
Stage #2: dimethyl sulfate In diethyl ether; hexane at 0℃; for 5.5h; Reflux; Inert atmosphere;
72%
With n-butyllithium 1)room temp., 2h,ether, hexane 2)reflux, 8h; Yield given. Multistep reaction;
9-bromophenanthrene
573-17-1

9-bromophenanthrene

phenylboronic acid
98-80-6

phenylboronic acid

9-phenylphenanthrene
844-20-2

9-phenylphenanthrene

Conditions
ConditionsYield
With potassium fluoride; o-(dicyclohexylphosphino)diisopropylbenzamide; tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl-formamide at 60℃; for 4h; Suzuki cross-coupling;99%
With 1,2,4,5-[3-(2,6-(iPr)2C6H3)imidazol-1-yl-CH2]4-Ph(4+)*4Br(-); potassium carbonate; palladium diacetate In ethanol at 20℃; for 22h; Suzuki cross-coupling;97%
Stage #1: 9-bromophenanthrene With [Pd(2-phenylpyridine)(Bmim)(saccharinate)] In toluene at 80℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
Stage #2: phenylboronic acid With sodium carbonate In water at 80℃; for 12h; Catalytic behavior; Temperature; Reagent/catalyst; Concentration; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;
96%
9-bromophenanthrene
573-17-1

9-bromophenanthrene

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

1-(9-phenanthryl)-2-nitrobenzene
911217-05-5

1-(9-phenanthryl)-2-nitrobenzene

Conditions
ConditionsYield
Stage #1: ortho-nitrobenzoic acid With potassium carbonate In various solvent(s) at 120℃; for 0.5h;
Stage #2: 9-bromophenanthrene With 1,10-Phenanthroline; copper(l) iodide In various solvent(s) at 160℃; for 24h; Further stages.;
99%
With potassium fluoride; copper(II) carbonate; bis(acetylacetonato)palladium(II); isopropyldiphenylphosphine In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Product distribution / selectivity; Molecular sieve;86 %Chromat.
copper(l) iodide; Phenanthroline; bis(acetylacetonato)palladium(II) In 1-methyl-pyrrolidin-2-one at 160℃; for 24h; Product distribution / selectivity; Molecular sieve;99 %Chromat.
9-bromophenanthrene
573-17-1

9-bromophenanthrene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

9-(naphthalen-1-yl) phenanthrene
119925-45-0

9-(naphthalen-1-yl) phenanthrene

Conditions
ConditionsYield
With potassium phosphate; 2C32H41O4P*Pd(2+)*2Cl(1-) In toluene at 110℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere;99%
With [Pd{C6H2(CH2CH2NH2)-(OMe)2,3,4} (μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.333333h; Suzuki-Miyaura coupling; Microwave irradiation;80%
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine In water at 20℃; for 24h; Suzuki-Miyaura reaction; Inert atmosphere; Micellar solution;78%
lithium trimethoxy(1,2,2-trifluorovinyl)borate

lithium trimethoxy(1,2,2-trifluorovinyl)borate

9-bromophenanthrene
573-17-1

9-bromophenanthrene

9-(1,2,2-trifluorovinyl)phenanthrene

9-(1,2,2-trifluorovinyl)phenanthrene

Conditions
ConditionsYield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 20 - 60℃; for 15.25h; Suzuki coupling; Inert atmosphere;99%
9-bromophenanthrene
573-17-1

9-bromophenanthrene

4-methoxy-2,6-dimethylphenylboronic acid
361543-99-9

4-methoxy-2,6-dimethylphenylboronic acid

C23H20O
1392512-39-8

C23H20O

Conditions
ConditionsYield
With Pd-PEPPSI-IPrAn; potassium tert-butylate In 1,4-dioxane at 80℃; for 24h; Suzuki coupling; Inert atmosphere;99%
9-bromophenanthrene
573-17-1

9-bromophenanthrene

S-phenyl tert-butylcarbamothioate
56741-04-9

S-phenyl tert-butylcarbamothioate

A

N-(tert-butyl)phenanthrene-9-carboxamide
1579273-93-0

N-(tert-butyl)phenanthrene-9-carboxamide

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
Stage #1: 9-bromophenanthrene With iodine; magnesium In 2-methyltetrahydrofuran at 60℃; for 1h; Schlenk technique; Inert atmosphere;
Stage #2: S-phenyl tert-butylcarbamothioate In 2-methyltetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique;
Stage #3: With ammonium hydroxide; oxygen In 2-methyltetrahydrofuran; water under 760.051 Torr; for 18h;
A 76%
B 99%
9-bromophenanthrene
573-17-1

9-bromophenanthrene

C28H37AgF2N2S

C28H37AgF2N2S

(difluoromethyl)(phenanthren-9-yl)thioether

(difluoromethyl)(phenanthren-9-yl)thioether

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate In tetrahydrofuran at 50℃; for 2h; Inert atmosphere; Schlenk technique;99%
2-methylfuran
534-22-5

2-methylfuran

9-bromophenanthrene
573-17-1

9-bromophenanthrene

2-methyl-5-(phenanthren-9-yl)furan

2-methyl-5-(phenanthren-9-yl)furan

Conditions
ConditionsYield
With [Pd(IPr*IMe)An(3-Cl-pyridinyl)Cl2]; potassium carbonate; acetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;99%
2-pentylfuran
3777-69-3

2-pentylfuran

9-bromophenanthrene
573-17-1

9-bromophenanthrene

2-pentyl-5-(phenanthren-9-yl)furan

2-pentyl-5-(phenanthren-9-yl)furan

Conditions
ConditionsYield
With [Pd(IPr*IMe)An(3-Cl-pyridinyl)Cl2]; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;99%
9-bromophenanthrene
573-17-1

9-bromophenanthrene

(5-chloro-2-methylphenyl)boronic acid
148839-33-2

(5-chloro-2-methylphenyl)boronic acid

C21H15Cl

C21H15Cl

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 4.5h; Inert atmosphere;98.6%
methanol
67-56-1

methanol

9-bromophenanthrene
573-17-1

9-bromophenanthrene

9-methoxyphenanthrene
5085-74-5

9-methoxyphenanthrene

Conditions
ConditionsYield
Stage #1: methanol With pyridine; copper(l) iodide; sodium at 80℃; Inert atmosphere;
Stage #2: 9-bromophenanthrene With pyridine for 42.1667h; Reflux; Inert atmosphere;
98%
Stage #1: methanol With sodium
Stage #2: 9-bromophenanthrene With pyridine; copper(l) iodide at 80℃; for 48h;
89%
With pyridine; copper(l) iodide; sodium for 18h; Heating;86%
1-ethenylcyclohexene
931-49-7

1-ethenylcyclohexene

9-bromophenanthrene
573-17-1

9-bromophenanthrene

9-(cyclohex-1-enylethynyl)phenanthrene
1052216-08-6

9-(cyclohex-1-enylethynyl)phenanthrene

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); triethylamine; XPhos In water at 20℃; Sonogashira coupling; Inert atmosphere; Micellar solution;98%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

9-bromophenanthrene
573-17-1

9-bromophenanthrene

3,7-Dihydro-1,3,7-trimethyl-8-(9-phenanthryl)-1H-purin-2,6-dion
99765-06-7

3,7-Dihydro-1,3,7-trimethyl-8-(9-phenanthryl)-1H-purin-2,6-dion

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; Trimethylacetic acid In N,N-dimethyl-formamide at 20 - 120℃; for 7.16667h; Inert atmosphere;98%
With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 20 - 140℃; for 36.1667h; Inert atmosphere; regioselective reaction;95%
9-bromophenanthrene
573-17-1

9-bromophenanthrene

3,5-dimethylphenyl boronic acid
172975-69-8

3,5-dimethylphenyl boronic acid

9-(3,5-dimethylphenyl)phenanthrene

9-(3,5-dimethylphenyl)phenanthrene

Conditions
ConditionsYield
Stage #1: 9-bromophenanthrene With [Pd(2-phenylpyridine)(Bmim)(saccharinate)] In toluene at 80℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
Stage #2: 3,5-dimethylphenyl boronic acid With sodium carbonate In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;
98%
9-bromophenanthrene
573-17-1

9-bromophenanthrene

C68H72B4N4O8Zn

C68H72B4N4O8Zn

C100H60N4Zn

C100H60N4Zn

Conditions
ConditionsYield
With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate In toluene at 130℃; under 2250.23 Torr; for 1h; Suzuki-Miyaura Coupling; Microwave irradiation; Inert atmosphere; Sealed tube;98%
dibenzoazepine
256-96-2

dibenzoazepine

9-bromophenanthrene
573-17-1

9-bromophenanthrene

N-(9-phenanthryl)iminostilbene

N-(9-phenanthryl)iminostilbene

Conditions
ConditionsYield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;98%

573-17-1Relevant articles and documents

A simple Hückel model-driven strategy to overcome electronic barriers to retro-Brook silylation relevant to aryne and bisaryne precursor synthesis

Neal, Edward A.,Werling,Jones, Christopher R.

supporting information, p. 1663 - 1666 (2021/02/26)

ortho-Silylaryl triflate precursors (oSATs) have been responsible for many recent advances in aryne chemistry and are most commonly accessed from the corresponding 2-bromophenol. A retro-BrookO- toC-silyl transfer is a key step in this synthesis but not all aromatic species are amenable to the transformation, with no functionalized bisbenzyneoSATs reported. Simple Hückel models are presented which show that the calculated aromaticity at the brominated position is an accurate predictor of successful retro-Brook reaction, validated synthetically by a new success and a predicted failure. From this, the synthesis of a novel difunctionalized bisaryne precursor has been tested, requiring different approaches to install the twoC-silyl groups. The first successful use of a disubstitutedo-silylaryl sulfonate bisbenzyne precursor in Diels-Alder reactions is then shown.

Chiral Ligand-Mediated Nucleophilic Aromatic Substitution of Naphthoic Acids: A Fast and Efficient Access to Axially Chiral Biaryls

Nguyen, Thi Thanh Thuy,Guyon, Hélène,Nguyen, Kim Phi Phung,Boussonnière, Anne,Mortier, Jacques,Castanet, Anne-Sophie

supporting information, p. 3829 - 3833 (2020/05/25)

A transition metal-free synthesis of enantioenriched biaryls from aryllithium species has been developed. This approach relies on atropoenantioselective nucleophilic aromatic substitution (SNAr) reaction of unprotected naphthoic acids. The ability of a diverse set of chiral ligands to mediate this transformation has been investigated. 1,2-diether ligands outperform their diamine counterparts and the best enantiocontrol was obtained with readily accessible enantiopure trans-1,2-dimethoxycyclohexane. This SNAr reaction offers an efficient and rapid access to enantioenriched binaphthalenes, phenylnaphthalene, and phenanthrylnaphthalenes (up to 94:6 er).

Preparation method of 9-bromophenanthrene

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Paragraph 0018; 0019; 0021-0024; 0025-0028, (2017/09/19)

The invention discloses a preparation method of 9-bromophenanthrene shown as in formula (II) that is shown in the description. The preparation method is characterized by including the steps of using phenanthrene shown in formula (I) that is shown in the description as a raw material, adding KBr bromination reagent, adding bromination reagent ZnAl-BrO3-LDHs into acetic acid and water mixed solvent, reacting at 20-70 DEG C for 2-5 hours to obtain reacted liquid that is post-treated to obtain the 9-bromophenanthrene shown as in the formula (II); the mas ratio of the phenanthrene shown as in the formula (I) to the KBr and ZnAlBrO3-LDHs is 1:0.9:0.6; the preparation method has the advantages that the preparation process is convenient, the reaction conditions are mild, low environmental pollution is caused, the requirements for equipment are low, bromine utilization rate is high, and the reaction time is short.

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