Conditions | Yield |
---|---|
With potassium bromate; tetrabutyl-ammonium chloride; ammonium bromide In water at 75℃; for 6h; Temperature; | 99.2% |
With bromine In water at 80℃; for 4h; regioselective reaction; | 94% |
With bromine In water at 80 - 85℃; for 4.5h; | 90.4% |
Conditions | Yield |
---|---|
With air; caesium carbonate In dimethyl sulfoxide at 20℃; for 3h; | 98% |
With oxygen; potassium hydroxide In tetrahydrofuran at 20℃; for 14h; | 98% |
With air; graphene-supported KOH composite In N,N-dimethyl-formamide at 20℃; for 8h; | 98% |
2-bromo-9H-fluoren-9-ol
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide In water at 100℃; for 24h; | 98% |
With N-Bromosuccinimide; potassium acetate In dichloromethane; water at 20℃; for 10h; Green chemistry; | 98% |
With picoline; tert.-butylhydroperoxide; chlorophyllin coppered trisodium salt In water; acetone at 80℃; for 10h; chemoselective reaction; | 98% |
With tert.-butylhydroperoxide; copper(II) acetate monohydrate In water at 80℃; for 8h; | 92% |
With 4-nitro-1-chlorobenzotriazole In water; acetic acid at 29.85℃; Kinetics; |
4-bromo-[1,1′-biphenyl]-2-carboxylic acid
2-bromofluoren-9-one
Conditions | Yield |
---|---|
Stage #1: 4-bromo-[1,1′-biphenyl]-2-carboxylic acid With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 8h; Stage #2: With aluminum (III) chloride at 20℃; for 6h; | 91% |
bei der Destillation; |
Conditions | Yield |
---|---|
With sodium persulfate; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; trifluorormethanesulfonic acid; palladium diacetate In dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; | 79% |
4'-bromo-[1,1'-biphenyl]-2-carbaldehyde
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; ferrocene In decane; acetonitrile at 20 - 90℃; for 24h; | 76% |
With carbon tetrabromide; oxygen In neat (no solvent) at 140℃; | 51% |
Conditions | Yield |
---|---|
With C31H25N2O3PPdS; potassium hydroxide In methanol; water at 50℃; for 6h; Catalytic behavior; Green chemistry; regioselective reaction; | 71% |
2,9-dibromo-9H-fluorene
A
2-bromofluoren-9-one
B
2,2'-dibromo-[9,9']bifluorenyl
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; iron(II) oxalate dihydrate at 155 - 160℃; for 0.166667h; | A n/a B 70% |
2-bromo-9H-fluorene
2,4,6-triphenylpyrylium tetrafluoroborate
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With oxygen In dichloromethane for 2h; Thermodynamic data; Irradiation; | 65% |
With oxygen In dichloromethane for 2h; Irradiation; Yield given; |
4'-bromo-[1,1'-biphenyl]-2-carbonitrile
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); water; silver trifluoroacetate In N,N-dimethyl acetamide; trifluoroacetic acid at 140℃; for 72h; Heck Reaction; Glovebox; Inert atmosphere; | 65% |
5-bromo-2-iodobenzaldehyde
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With cesium fluoride; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium(0) In toluene; acetonitrile at 110℃; for 12h; | 61% |
Conditions | Yield |
---|---|
With bromine In water at 80℃; for 4h; | A n/a B 41% |
With N-Bromosuccinimide; methanesulfonic acid In chloroform |
2,7-dibromo-9H-fluorene
A
2,7-dibromofluorene-9-one
B
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide | A 31% B 23% |
4'-bromo-[1,1'-biphenyl]-2-carboxylic acid
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With potassium carbonate; triphenylphosphine In 1,2-dichloro-ethane at 20℃; for 24h; Irradiation; Schlenk technique; Green chemistry; | 30% |
2-bromo-phenanthrene-9,10-dione
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With potassium hydroxide |
2-bromo-phenanthrene-9,10-dione
A
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With potassium hydroxide at 80 - 90℃; |
2,2'-dibromo-9,9'-dinitro-[9,9']bifluorenyl
2-bromofluoren-9-one
2-bromo-9H-fluoren-9-ol
bromamine T
A
2-bromofluoren-9-one
B
toluene-4-sulfonamide
Conditions | Yield |
---|---|
With acetic acid for 24h; | |
With acetic acid at 30℃; Kinetics; Mechanism; Thermodynamic data; E(activ.), ΔH(activ.), ΔS(activ.), Γ(activ.); |
2-Amino-3-brom-fluorenon
2-bromofluoren-9-one
Conditions | Yield |
---|---|
(i) NaNO2, H2SO4, (ii) aq. H3PO2; Multistep reaction; |
1-amino-7-bromo-9H-fluoren-9-one
2-bromofluoren-9-one
Conditions | Yield |
---|---|
(i) NaNO2, aq. HCl, (ii) H3PO2; Multistep reaction; |
7-Brom-fluorenon-(9)-carbonsaeure-(4)
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With quinoline; copper |
Conditions | Yield |
---|---|
at 100℃; |
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With aluminium trichloride |
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With sulfuric acid at 50℃; |
2-bromofluoren-9-one
Conditions | Yield |
---|---|
bei der Destillation; |
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With air |
2-bromo-phenanthrene-9,10-dione
A
2-bromofluoren-9-one
Conditions | Yield |
---|---|
at 80 - 90℃; |
2-bromo-9-aci-nitro-fluorene
2-bromofluoren-9-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ethanol View Scheme |
Conditions | Yield |
---|---|
With copper(l) iodide; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 50℃; for 17h; Sonogashira reaction; | 100% |
2-bromofluoren-9-one
phenylmagnesium bromide
2-bromo-9-phenyl-9H-fluoren-9-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 0.333333h; | 100% |
In diethyl ether at 0℃; for 12h; Inert atmosphere; | 95% |
In tetrahydrofuran at 0 - 20℃; for 12h; | 89% |
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 6h; Reflux; | 100% |
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; copper dichloride In water; dimethyl sulfoxide at 100℃; for 4h; Reagent/catalyst; | 99.9% |
With water; sodium hydroxide In ethanol at 90℃; for 6h; Temperature; Solvent; | 83% |
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere; | 71% |
(1R,5S)-tert-butyl 3,6-diaza-bicyclo[3.2.0]heptane-6-carboxylate
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); racemic-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl In toluene at 90℃; for 16h; | 98% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 140℃; for 6h; Suzuki Coupling; | 98% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; for 4h; Schlenk technique; Inert atmosphere; Sealed tube; | 94% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 60℃; Reflux; | 92% |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3,3'-bipyridine With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran at -78 - 20℃; for 4h; | 98% |
Conditions | Yield |
---|---|
Stage #1: 3-(2-bromophenyl)pyridine With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran at -78 - 20℃; for 4h; | 98% |
2-bromofluoren-9-one
1-bromo-4-(2′-ethylhexyloxy)benzene
2-bromo-9-(4-(2-ethylhexyloxy)phenyl)-fluoren-9-ol
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-(2′-ethylhexyloxy)benzene With iodine; magnesium In tetrahydrofuran Stage #2: 2-bromofluoren-9-one In tetrahydrofuran for 5h; Heating; | 95% |
2-bromofluoren-9-one
(2-bromo-9H-fluoren-9-ylidene)hydrazine
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol for 3h; Heating; | 95% |
With hydrazine hydrate In methanol for 3h; Reflux; Inert atmosphere; | 91% |
With hydrazine hydrate In ethanol for 6h; Inert atmosphere; Reflux; |
Conditions | Yield |
---|---|
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In diethyl ether; ethanol at 110℃; for 0.166667h; Suzuki-Miyaura cross-coupling; microwave irradiation; | 95% |
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromophenyl)[1]benzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran at 20℃; for 1h; | 95% |
Conditions | Yield |
---|---|
With methanesulfonic acid at 50℃; for 12h; | 95% |
2-bromofluoren-9-one
2-bromo-7-nitro-9H-fluoren-9-one
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid In water for 4h; Reflux; regioselective reaction; | 93% |
With sulfuric acid; nitric acid In water at 80 - 120℃; for 4.5h; | 76.4% |
With sulfuric acid; nitric acid In water at 80 - 85℃; for 4h; | 76.4% |
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; XPhos for 12h; Reflux; Inert atmosphere; | 93% |
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 50 - 100℃; Inert atmosphere; | 74% |
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen; acetic acid at 60℃; for 7h; | 93% |
2-bromofluoren-9-one
2-bromo-9H-fluoren-9-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 0 - 20℃; | 91% |
With sodium tetrahydroborate In methanol at 0 - 20℃; | 91% |
With sodium tetrahydroborate In isopropyl alcohol at 25 - 45℃; Kinetics; |
2-Bromobiphenyl
2-bromofluoren-9-one
9-(biphenyl-2-yl)-2-bromo-9-fluorenol
Conditions | Yield |
---|---|
Stage #1: 2-Bromobiphenyl With magnesium; ethylene dibromide In diethyl ether at 50℃; for 3h; Grignard Reaction; Stage #2: 2-bromofluoren-9-one In diethyl ether at 20 - 50℃; for 27h; Stage #3: With water In diethyl ether at 20℃; | 91% |
Stage #1: 2-Bromobiphenyl With magnesium; ethylene dibromide In diethyl ether for 3h; Heating / reflux; Stage #2: 2-bromofluoren-9-one In diethyl ether for 2h; Heating / reflux; Stage #3: With water; ammonium chloride | 90% |
Stage #1: 2-Bromobiphenyl With magnesium In diethyl ether; ethylene dibromide for 3h; Inert atmosphere; Reflux; Stage #2: 2-bromofluoren-9-one In diethyl ether; ethylene dibromide for 14h; Inert atmosphere; Reflux; | 90% |
Conditions | Yield |
---|---|
Stage #1: C24H14BrNS With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran for 18h; | 91% |
2-bromofluoren-9-one
2-bromo-9,9-dichlorofluorene
Conditions | Yield |
---|---|
With phosphorus pentachloride; trichlorophosphate at 80 - 90℃; for 24h; Reagent/catalyst; Solvent; Temperature; Green chemistry; | 90.7% |
With phosphorus pentachloride at 180℃; |
Conditions | Yield |
---|---|
In methanesulfonic acid at 152℃; for 24h; Inert atmosphere; | 90% |
With trichlorophosphate at 120℃; | 87% |
With trichlorophosphate at 120℃; | 87% |
2-bromofluoren-9-one
9-(biphenyl-2-yl)-2-bromo-9-fluorenol
Conditions | Yield |
---|---|
Stage #1: 2-Bromobiphenyl With 1,1-Dibromoethane; magnesium In diethyl ether at 20℃; for 3.5h; Heating / reflux; Stage #2: 2-bromofluoren-9-one In diethyl ether at 20℃; Heating / reflux; | 90% |
Stage #1: 2-Bromobiphenyl With magnesium; ethylene dibromide In diethyl ether for 3h; Heating / reflux; Stage #2: 2-bromofluoren-9-one In diethyl ether at 20℃; for 14h; Heating / reflux; Stage #3: With water; ammonium chloride In diethyl ether | 90% |
Stage #1: 2-Bromobiphenyl With magnesium In tetrahydrofuran Stage #2: 2-bromofluoren-9-one In tetrahydrofuran at 20℃; for 14h; Heating / reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran |
2-bromofluoren-9-one
Conditions | Yield |
---|---|
Stage #1: 2-bromofluoren-9-one With sulfuric acid; acetic acid In water at 60℃; for 1h; Stage #2: With iodine; periodic acid In water at 85℃; for 16h; | 90% |
Stage #1: 2-bromofluoren-9-one With sulfuric acid In water; acetic acid at 60℃; for 1h; Inert atmosphere; Stage #2: With iodine; periodic acid In water; acetic acid at 85℃; for 18h; Inert atmosphere; regioselective reaction; | 89% |
Conditions | Yield |
---|---|
Stage #1: 1,4-diethynylbenzene With n-butyllithium In hexane at -10℃; for 1.5h; Inert atmosphere; Stage #2: 2-bromofluoren-9-one In hexane at -10 - 20℃; Inert atmosphere; | 90% |
2-bromofluoren-9-one
N-(2-bromophenyl)-N-phenylbenzenamine
(2'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene])
Conditions | Yield |
---|---|
Stage #1: N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran at -78 - 20℃; | 90% |
Stage #1: N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: 2-bromofluoren-9-one In tetrahydrofuran; hexane for 3h; Stage #3: With hydrogenchloride In water; acetic acid for 6h; Reflux; | 74.5% |
Stage #1: 2-bromofluoren-9-one; N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran at -78℃; for 4h; Inert atmosphere; Stage #2: With hydrogenchloride; acetic acid for 1h; Reflux; Inert atmosphere; | 63% |
2-bromofluoren-9-one
Conditions | Yield |
---|---|
With (bis-(2-methoxyethyl)amino)sulfur trufluoride In ethanol for 48h; | 90% |
Multi-step reaction with 2 steps 1: trichlorophosphate; phosphorus pentachloride / 24 h / 80 - 90 °C / Green chemistry 2: iron(III) chloride; hydrogen fluoride / toluene / 24 h / 10 - 30 °C / Inert atmosphere View Scheme |
The 2-Bromo-9-fluorenone, with the CAS registry number 3096-56-8, is also known as 9H-Fluoren-9-one, 2-bromo-. It belongs to the product categories of Fluorene Derivatives; Fluorenes, Flurenones; Electronic Chemicals; Fluorenes & Fluorenones; Fluorenones; C13 to C14; Carbonyl Compounds; Ketones. This chemical's molecular formula is C13H7BrO and molecular weight is 259.0981. Its systematic name is called 2-bromo-9H-fluoren-9-one. This chemical is yellow powder which should be sealed and stored in cool and dry place.
Physical properties of 2-Bromo-9-fluorenone: (1)ACD/LogP: 4.35; (2)#H bond acceptors: 1; (3)Index of Refraction: 1.691; (4)Molar Refractivity: 61.61 cm3; (5)Molar Volume: 161 cm3; (6)Surface Tension: 56 dyne/cm; (7)Density: 1.609 g/cm3; (8)Flash Point: 131.3 °C; (9)Enthalpy of Vaporization: 64.26 kJ/mol; (10)Boiling Point: 392.8 °C at 760 mmHg; (11)Vapour Pressure: 2.23E-06 mmHg at 25°C.
Preparation: this chemical can be prepared by 2,4,6-triphenyl-pyranylium; tetrafluoroborate and 2-bromo-fluorene. This reaction will need reagent O2 and solvent CH2Cl2. The reaction time is 2 hours. The yield is about 65%.
Uses of 2-Bromo-9-fluorenone: it can be used to produce 2-(3-pyridyl)-9-fluorenone by heating. This reaction will need reagent KOH, tetrabutylammonium bromide, tetrakis(triphenylphosphine)palladium and solvent tetrahydrofuran with reaction time of 18 hours. The yield is about 20%.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing and eye/face protection.
You can still convert the following datas into molecular structure:
(1)SMILES: Brc3ccc2c1ccccc1C(=O)c2c3
(2)InChI: InChI=1/C13H7BrO/c14-8-5-6-10-9-3-1-2-4-11(9)13(15)12(10)7-8/h1-7H
(3)InChIKey: MTCARZDHUIEYMB-UHFFFAOYAR
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