2,7-dibromo-9H-fluorene
methyl iodide
2,7-dibromo-9,9-dimethyl-9H-fluorene
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide for 5h; Sonication; | 99% |
With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide at 20℃; for 5h; Sonication; | 99% |
With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide for 5h; Sonication; | 99% |
2,7-dibromo-9H-fluorene
2,7-dibromo-9,9-dimethyl-9H-fluorene
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide at 20℃; for 5h; | 99% |
9,9-dimethyl-9H-fluorene
2,7-dibromo-9,9-dimethyl-9H-fluorene
Conditions | Yield |
---|---|
With bromine In chloroform for 4h; Cooling with ice; | 76% |
With bromine |
methyl iodide
2,7-dibromo-9,9-dimethyl-9H-fluorene
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9H-fluorene With potassium tert-butylate In dimethyl sulfoxide at 5℃; Stage #2: methyl iodide In dimethyl sulfoxide at 5℃; |
2,7-dibromo-9,9-dimethyl-9H-fluorene
3,5-bis-trifluromethylphenylboronic acid
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 80℃; for 1.5h; Suzuki Coupling; | 98% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
trimethyltin(IV)chloride
2,7-bis(trimethylstannyl)-9,9-dimethylfluorene
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1.25h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃; for 6.08333h; | 97% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
dimesitylfluoroborane
(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)dimesitylborane
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: dimesitylfluoroborane In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 94% |
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: dimesitylfluoroborane In tetrahydrofuran; hexane at 20℃; for 6h; | 80% |
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: dimesitylfluoroborane In tetrahydrofuran; hexane for 12h; | 63% |
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran Stage #2: dimesitylfluoroborane |
4-trifluoromethylphenylamine
2,7-dibromo-9,9-dimethyl-9H-fluorene
C22H17BrF3N
Conditions | Yield |
---|---|
With sodium t-butanolate; C30H48FeP2; palladium dichloride In 1,4-dioxane for 3h; Heating / reflux; | 92% |
With sodium t-butanolate; C30H48FeP2; palladium dichloride In 1,4-dioxane for 3h; Heating / reflux; | 92 %Chromat. |
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2,7-dibromo-9,9-dimethyl-9H-fluorene
4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9,9-dimethyl-9H-fluoren-2-yl]-[1,3,2]dioxaborolane
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane at 20℃; for 2h; | 90% |
With n-butyllithium In diethyl ether at -78 - 20℃; for 14h; Inert atmosphere; | 60.5% |
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78 - 0℃; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; | 33% |
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 25h; |
2,7-dibromo-9,9-dimethyl-9H-fluorene
N,N-dimethyl-formamide
7-bromo-9,9-dimethyl-9H-fluorene-2-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 2h; | 90% |
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃; | 90% |
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 25℃; for 10h; Inert atmosphere; Schlenk technique; | 90% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
7-bromo-9,9-dimethyl-9H-fluorene-2-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran at -78 - 25℃; for 10h; Inert atmosphere; Schlenk technique; | 90% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
Conditions | Yield |
---|---|
With water-d2; potassium carbonate; silver carbonate; cyclohexyldiphenylphosphine In toluene at 120℃; for 12h; | 90% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
1-pyrenylboronic acid
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 20 - 77℃; for 5.5h; Suzuki Coupling; | 89% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 4h; Suzuki Coupling; Reflux; | 73% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
N-methylaniline
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With palladium diacetate; johnphos; sodium t-butanolate In toluene at 20℃; for 0.75h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Stage #2: N-methylaniline In toluene at 180℃; for 1h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Microwave irradiation; | 89% |
((10-(naphthalen-1-yl)anthracen-9-yl)boronic acid)
2,7-dibromo-9,9-dimethyl-9H-fluorene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 4h; Suzuki Coupling; Reflux; | 86% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
N-methylaniline
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With palladium diacetate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium t-butanolate In toluene at 20℃; for 0.5h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Stage #2: N-methylaniline In toluene at 180℃; for 0.75h; Reagent/catalyst; Solvent; Buchwald-Hartwig Coupling; Microwave irradiation; Schlenk technique; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene; aniline In benzene at 50℃; for 0.333333h; Inert atmosphere; Stage #2: With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In benzene Reflux; Inert atmosphere; | 85.63% |
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 12h; Inert atmosphere; | |
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 12h; Inert atmosphere; |
2,7-dibromo-9,9-dimethyl-9H-fluorene
1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene
1-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)pyrene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Inert atmosphere; Reflux; | 85% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In toluene at 82℃; for 11h; | 85% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 2h; Inert atmosphere; Reflux; | 85% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
9,9-dimethyl-9H-fluoren-2-yl-2-boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water for 14h; Reflux; Inert atmosphere; Schlenk technique; | 84% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
bis(pinacol)diborane
4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9,9-dimethyl-9H-fluoren-2-yl]-[1,3,2]dioxaborolane
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane for 4h; Inert atmosphere; Heating; | 83% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate at 90℃; for 48h; Inert atmosphere; | 78% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate at 90℃; for 48h; | 78% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
diphenylamine
2-bromo-7-N,N’-diphenylamino-9,9’-dimethyl-9H-fluorene
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 80℃; for 2h; Schlenk technique; | 83% |
With 18-crown-6 ether; copper; potassium carbonate; potassium iodide In 1,2-dichloro-benzene at 200℃; for 24h; Inert atmosphere; | 79% |
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 20 - 200℃; for 24h; Inert atmosphere; | 79% |
pyrrolidine
2,7-dibromo-9,9-dimethyl-9H-fluorene
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With palladium diacetate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium t-butanolate In toluene at 20℃; for 0.5h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Stage #2: pyrrolidine In toluene at 180℃; for 0.75h; Buchwald-Hartwig Coupling; Microwave irradiation; Schlenk technique; Inert atmosphere; | 83% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
phenylboronic acid
9,9-dimethyl-2,7-diphenyl-9H-fluorene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate In water; toluene at 90℃; Inert atmosphere; Schlenk technique; | 82.6% |
With potassium carbonate In ethanol; water; toluene at 120℃; for 3h; Inert atmosphere; | |
With potassium carbonate; tetrabutylammomium bromide; palladium diacetate In water at 70℃; for 24h; | |
Suzuki Coupling; |
styrene
2,7-dibromo-9,9-dimethyl-9H-fluorene
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); N-Methyldicyclohexylamine; tetrabutylammomium bromide In toluene at 80℃; Inert atmosphere; Schlenk technique; | 82.5% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
N,N-dimethyl-formamide
9,9-dimethyl-9H-fluorene-2,7-dicarbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; N,N-dimethyl-formamide at -78 - 25℃; for 10h; Inert atmosphere; Schlenk technique; | 82% |
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With magnesium In tetrahydrofuran for 16h; Grignard reaction; Reflux; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 5h; Cooling with ice; | 66% |
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 3h; | 62% |
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran for 12h; | 60% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
aniline
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With palladium diacetate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium t-butanolate In toluene at 20℃; for 0.5h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Stage #2: aniline In toluene at 180℃; for 0.75h; Buchwald-Hartwig Coupling; Microwave irradiation; Schlenk technique; Inert atmosphere; | 82% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
9,9-dimethyl-9H-fluorene-2,7-dicarbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,7-dibromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran at -78 - 25℃; for 10h; Inert atmosphere; Schlenk technique; | 82% |
2,7-dibromo-9,9-dimethyl-9H-fluorene
2,7-di(p-tolylthio)-9,9-dimethyl-9H-fluorene
Conditions | Yield |
---|---|
With palladium diacetate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; | 81% |
1H-imidazole
2,7-dibromo-9,9-dimethyl-9H-fluorene
2,7-bis(1H-imidazol-1-yl)-9,9-dimethyl-9H-fluorene
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere; | 81% |
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 119.84℃; for 36h; Inert atmosphere; | 76.1% |
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 8h; | 76% |
The systematic name of this chemical is 2,7-dibromo-9,9-dimethyl-9H-fluorene. With the CAS registry number 28320-32-3, it is also named as 9H-Fluorene,2,7-dibromo-9,9-dimethyl-. The product's categories are Fluorene Derivatives; Electronic Chemicals. The molecular weight of 2,7-Dibromo-9,9-dimethylfluorene is C15H12Br2 and molecular weight is 352.06.
The other characteristics of 2,7-Dibromo-9,9-dimethylfluorene can be summarized as: (1)ACD/LogP: 8.06; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7; (4)ACD/LogD (pH 7.4): 7; (5)ACD/BCF (pH 5.5): 78047; (6)ACD/BCF (pH 7.4): 78047; (7)ACD/KOC (pH 5.5): 110542; (8)ACD/KOC (pH 7.4): 110542; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.635; (14)Molar Refractivity: 78.497 cm3; (15)Molar Volume: 219.117 cm3; (16)Polarizability: 31.119×10-24 cm3; (17)Surface Tension: 46.054 dyne/cm; (18)Density: 1.607 g/cm3; (19)Flash Point: 230.294 °C; (20)Enthalpy of Vaporization: 62.744 kJ/mol; (21)Boiling Point: 401.811 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
People can use the following data to convert to the molecule structure.
1. SMILES:Brc2ccc3c1ccc(Br)cc1C(C)(C)c3c2
2. InChI:InChI=1/C15H12Br2/c1-15(2)13-7-9(16)3-5-11(13)12-6-4-10(17)8-14(12)15/h3-8H,1-2H3
3. InChIKey:LONBOJIXBFUBKQ-UHFFFAOYAJ
4. Std. InChI:InChI=1S/C15H12Br2/c1-15(2)13-7-9(16)3-5-11(13)12-6-4-10(17)8-14(12)15/h3-8H,1-2H3
5. Std. InChIKey:LONBOJIXBFUBKQ-UHFFFAOYSA-N
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