Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
9-bromophenanthrene
Conditions | Yield |
---|---|
In tetrahydrofuran at 25℃; for 60h; | 18% |
tetrachloromethane
N-Bromosuccinimide
phenanthrene
9-bromophenanthrene
9,10-dibromo-9,10-dihydro-phenanthrene
silver(I) acetate
acetic acid
9-bromophenanthrene
9-bromophenanthrene
Conditions | Yield |
---|---|
With RhCl(PPh3)3 at 300℃; |
9-bromophenanthrene
A
9-bromophenanthrene
B
2,7-dibromophenanthrene
Conditions | Yield |
---|---|
With chloroform; bromine |
Conditions | Yield |
---|---|
at 0 - 76℃; |
Conditions | Yield |
---|---|
at 0 - 76℃; |
phenanthrene
bromine
A
9-bromophenanthrene
B
9,10-dibromo-9,10-dihydro-phenanthrene
9,10-dibromo-9,10-dihydro-phenanthrene
A
9-bromophenanthrene
B
hydrogen bromide
Conditions | Yield |
---|---|
beim Erhitzen fuer sich; |
9,10-dibromo-9,10-dihydro-phenanthrene
water
A
9-bromophenanthrene
B
hydrogen bromide
Conditions | Yield |
---|---|
im geschlossenen Rohr; |
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
With bromine at 100℃; for 4h; Reflux; Ionic liquid; |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
9-bromophenanthrene
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; | 100% |
9-bromophenanthrene
2,6-dimethylbenzene boronic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
ortho-nitrobenzoic acid
1-(9-phenanthryl)-2-nitrobenzene
Conditions | Yield |
---|---|
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
1-Naphthylboronic acid
9-(naphthalen-1-yl) phenanthrene
Conditions | Yield |
---|---|
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% |
9-bromophenanthrene
Conditions | Yield |
---|---|
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 20 - 60℃; for 15.25h; Suzuki coupling; Inert atmosphere; | 99% |
9-bromophenanthrene
4-methoxy-2,6-dimethylphenylboronic acid
C23H20O
Conditions | Yield |
---|---|
With Pd-PEPPSI-IPrAn; potassium tert-butylate In 1,4-dioxane at 80℃; for 24h; Suzuki coupling; Inert atmosphere; | 99% |
9-bromophenanthrene
S-phenyl tert-butylcarbamothioate
A
N-(tert-butyl)phenanthrene-9-carboxamide
B
diphenyldisulfane
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 4.5h; Inert atmosphere; | 98.6% |
Conditions | Yield |
---|---|
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
9-bromophenanthrene
9-(cyclohex-1-enylethynyl)phenanthrene
Conditions | Yield |
---|---|
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
9-bromophenanthrene
3,7-Dihydro-1,3,7-trimethyl-8-(9-phenanthryl)-1H-purin-2,6-dion
Conditions | Yield |
---|---|
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
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; | 98% |
Product Name: 9-Bromophenanthrene (CAS NO.573-17-1)
IUPAC Name: 9-bromophenanthrene
Molecular Formula: C14H9Br
Molecular Weight: 257.125260 g/mol
Appearance: Very slightly yellow solid
Density: 1.479g/cm3
Melting Point: 60-64 °C(lit.)
Boiling Point: 180-190 °C 2 mm Hg(lit.)
Flash Point: 110 °C
Solubility:chloroform: 50 mg/mL, clear
BRN: 1869927
EINECS: 209-351-6
Index of Refraction: 1.733
Molar Refractivity: 69.62 cm3
Molar Volume: 173.8 cm3
Categories: Aromatic Compounds; blocks; Bromides; Miscellaneous; Aryl; C13 to C37+; Halogenated Hydrocarbons
9-Bromophenanthrene (CAS NO.573-17-1) is used in organic synthesis.
Safety Information of 9-Bromophenanthrene (CAS NO.573-17-1):
Hazard Codes:Xi,Xn
Risk Statements:20/21/22-36/37/38
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:22-24/25-36-26
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:3
RTECS:SF7197000
F:8
Hazard Note:Irritant
HS Code:29036990
9-Bromophenanthrene , its CAS NO. is 573-17-1, the synonyms are 9-Phenathryl bromide ; Phenanthrene, 9-bromo- .
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