3-(4-bromophenyl)propionic acid
6-bromoindan-1-one
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In dichloromethane at 80℃; for 1h; Friedel-Crafts Acylation; High pressure; Inert atmosphere; Green chemistry; | 100% |
With chlorosulfonic acid at 0℃; for 1h; Friedel-Crafts reaction; | 98% |
With aluminum (III) chloride In dichloromethane for 3h; Reflux; | 80% |
6-hydroxy-1-indanone
tert-butyldimethylsilyl chloride
6-bromoindan-1-one
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane | 98% |
3-(4-bromophenyl)propanoyl chloride
6-bromoindan-1-one
Conditions | Yield |
---|---|
With aluminium trichloride In carbon disulfide | 91% |
With aluminium trichloride In carbon disulfide for 3h; Heating / reflux; | 47% |
With aluminium trichloride In dichloromethane |
C15H13BrN2O3
6-bromoindan-1-one
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In chloroform at 50℃; for 4h; Friedel Crafts acylation; Inert atmosphere; | 88% |
6-aminoindan-1-one
6-bromoindan-1-one
Conditions | Yield |
---|---|
Stage #1: 6-aminoindan-1-one With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: With copper(I) bromide In water at 0 - 20℃; for 2h; | 71% |
3-(4-bromophenyl)propionic acid
A
6-bromoindan-1-one
B
6-bromo-2-[3-(4-bromophenyl)-1-oxopropyl]-indan-1-one
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; trifluoroacetic acid In dichloromethane at 20℃; for 2h; | A 8% B 70% |
Conditions | Yield |
---|---|
Stage #1: 3-(4-bromophenyl)propionic acid With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h; Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 2h; | A 8% B 70% |
Stage #1: 3-(4-bromophenyl)propionic acid With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h; Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 2h; | A 62% B n/a |
inden-1-one
A
4-bromo-2,3-dihydroinden-1-one
B
6-bromoindan-1-one
C
5-Bromo-1-indanone
D
4,7-dibromo-1-indanone
Conditions | Yield |
---|---|
With aluminium trichloride; bromine at 110℃; for 0.5h; Further byproducts given; | A 47% B 21% C 3% D 2% |
inden-1-one
A
4-bromo-2,3-dihydroinden-1-one
B
6-bromoindan-1-one
C
5-Bromo-1-indanone
Conditions | Yield |
---|---|
With aluminium trichloride; bromine at 110℃; for 0.5h; Further byproducts given; | A 47% B 21% C 3% D 1% |
Conditions | Yield |
---|---|
With Pseudomonas putida UV4 for 7h; | A 28% B 16% |
inden-1-one
6-bromoindan-1-one
Conditions | Yield |
---|---|
Stage #1: inden-1-one With aluminum (III) chloride for 0.216667h; Stage #2: With bromine at 0 - 80℃; for 0.25h; | 19% |
Multi-step reaction with 3 steps 1.1: potassium nitrate; sulfuric acid / 1.5 h / 0 - 5 °C 2.1: iron; ammonium chloride / water; ethanol / 80 °C 3.1: sodium nitrite; hydrogenchloride / water / 0 °C 3.2: 2 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
With Pseudomonas putida UV4 for 7h; | A 4% B n/a |
3-(4-bromophenyl)propionic acid
A
6-bromoindan-1-one
Conditions | Yield |
---|---|
With sulfuric acid |
Conditions | Yield |
---|---|
With aluminium trichloride; bromine 1.) 10 min, 2.) 80 deg C, 5 min; Yield given. Multistep reaction. Yields of byproduct given; | |
With hydrogenchloride; bromine; aluminium trichloride In tetrahydrofuran; hexane; water |
6-bromoindan-1-one
Conditions | Yield |
---|---|
With sulfuric acid at 145℃; man giesst auf Eis; |
5-(4-bromo-benzyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione
6-bromoindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2O / acetonitrile / 0.5 h / 120 °C / microwave irradiation 2: 98 percent / chlorosulfonic acid / 1 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 63 percent / triethylammonium formate 2: H2O / acetonitrile / 0.5 h / 120 °C / microwave irradiation 3: 98 percent / chlorosulfonic acid / 1 h / 0 °C View Scheme |
trans-4-bromocinnamic acid
6-bromoindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2 / Pd/C / methanol 2: (COCl)2 / CH2Cl2 3: aluminum trichloride / CH2Cl2 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: piperidine / pyridine 2: H2 / Pd/C / methanol 3: (COCl)2 / CH2Cl2 4: aluminum trichloride / CH2Cl2 View Scheme |
5-Bromo-1-indanone
6-bromoindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / sodium borohydride / methanol / 2 h / 20 °C 2: 92 percent / p-TsOH / benzene / 2 h / Heating 3: 28 percent / Pseudomonas putida UV4 / 7 h View Scheme |
5-bromo-1-indanol
6-bromoindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 92 percent / p-TsOH / benzene / 2 h / Heating 2: 28 percent / Pseudomonas putida UV4 / 7 h View Scheme |
6-Bromo-2,3-dihydro-1H-inden-1-ol
6-bromoindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 87 percent / p-TsOH / benzene / 2 h / Heating 2: 4 percent / Pseudomonas putida UV4 / 7 h View Scheme |
diethyl 2-(4-bromobenzyl)malonate
6-bromoindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: aq. KOH / 4.5 h / Heating 2: aq. H2SO4 / 18 h / Heating 3: (COCl)2; DMF / 18 h / 20 °C 4: AlCl3 / CH2Cl2 / 3.5 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 95 percent / KOH / acetic acid; H2O; tetrahydrofuran 2: 85 percent / 165 °C 3: thionyl chloride 4: 91 percent / AlCl3 / CS2 View Scheme |
2-[(4-bromophenyl)methyl]propanedioic acid
6-bromoindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aq. H2SO4 / 18 h / Heating 2: (COCl)2; DMF / 18 h / 20 °C 3: AlCl3 / CH2Cl2 / 3.5 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 85 percent / 165 °C 2: thionyl chloride 3: 91 percent / AlCl3 / CS2 View Scheme |
1-bromomethyl-4-bromobenzene
6-bromoindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: NaH / 1,2-dimethoxy-ethane / 2 h / 20 °C 1.2: 57 percent / 1,2-dimethoxy-ethane / 18 h / Heating 2.1: aq. KOH / 4.5 h / Heating 3.1: aq. H2SO4 / 18 h / Heating 4.1: (COCl)2; DMF / 18 h / 20 °C 5.1: AlCl3 / CH2Cl2 / 3.5 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: 74 percent / NaOEt / Heating 2: 95 percent / KOH / acetic acid; H2O; tetrahydrofuran 3: 85 percent / 165 °C 4: thionyl chloride 5: 91 percent / AlCl3 / CS2 View Scheme | |
Multi-step reaction with 2 steps 1: trifluoroacetic acid; lithium diisopropyl amide / tetrahydrofuran 2: hydrogenchloride; thionyl chloride / aluminium trichloride / dichloromethane View Scheme |
methyl 4-bromocinnamate
6-bromoindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon / methanol 2: trifluorormethanesulfonic acid / 25 °C / Cooling with ice View Scheme |
methyl 3-(4-bromopehynl)propanoate
6-bromoindan-1-one
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 25℃; Cooling with ice; |
6-nitroindan-1-one
6-bromoindan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: iron; ammonium chloride / water; ethanol / 80 °C 2.1: sodium nitrite; hydrogenchloride / water / 0 °C 2.2: 2 h / 0 - 20 °C View Scheme |
6-bromoindan-1-one
6-Bromo-2,3-dihydro-1H-inden-1-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 10 - 20℃; for 3h; | 100% |
With sodium borohydrid In methanol | 99% |
With methanol; sodium tetrahydroborate at 20℃; for 2h; Temperature; Concentration; Inert atmosphere; | 99% |
6-bromoindan-1-one
N-4-chlorophenylhydrazine
Conditions | Yield |
---|---|
With acetic acid In ethanol for 0.5h; Heating / reflux; | 100% |
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; benzene Suzuki coupling; Heating; | 99% |
6-bromoindan-1-one
dimethyl zinc(II)
6-bromo-1,1-dimethyl-2,3-dihydro-1H-indene
Conditions | Yield |
---|---|
Stage #1: dimethyl zinc(II) With titanium tetrachloride In dichloromethane; toluene at -30 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 6-bromoindan-1-one In dichloromethane; toluene at -10℃; for 4h; | 99% |
Stage #1: dimethyl zinc(II) With titanium(III) chloride In dichloromethane; toluene at 40℃; for 0.333333h; Stage #2: 6-bromoindan-1-one In dichloromethane; toluene at 20℃; for 18h; | 94% |
Stage #1: dimethyl zinc(II) With titanium tetrachloride In dichloromethane; toluene at 40℃; for 0.333333h; Stage #2: 6-bromoindan-1-one In dichloromethane; toluene at 20℃; for 18h; | 94% |
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; tert-butyl XPhos In 1,4-dioxane at 80℃; for 3h; Inert atmosphere; Schlenk technique; | 98% |
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In 1,4-dioxane; water at 90℃; for 5h; Inert atmosphere; Sealed tube; | 97% |
6-bromoindan-1-one
bis(pinacol)diborane
6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H-inden-1-one
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In toluene at 90℃; for 12h; Inert atmosphere; | 96% |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In toluene at 90℃; for 12h; Inert atmosphere; | 96% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 100℃; for 1h; Microwave irradiation; | 95% |
6-bromoindan-1-one
Methyltriphenylphosphonium bromide
Conditions | Yield |
---|---|
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 6-bromoindan-1-one In tetrahydrofuran at 20℃; Inert atmosphere; | 96% |
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.583333h; Stage #2: 6-bromoindan-1-one In tetrahydrofuran at 20℃; for 1h; Stage #3: With water In tetrahydrofuran | 93.4% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexanes at 0℃; for 1h; Stage #2: 6-bromoindan-1-one In tetrahydrofuran; hexanes | 62% |
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran for 1h; Inert atmosphere; Cooling with ice; Stage #2: 6-bromoindan-1-one In tetrahydrofuran for 0.5h; Cooling with ice; | 60% |
6-bromoindan-1-one
ethylene glycol
6‘-bromo-2‘,3‘-dihydrospiro[[1,3]dioxolane-2,1‘-indene]
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene at 115℃; for 48h; Dean-Stark; Inert atmosphere; | 95% |
With toluene-4-sulfonic acid In benzene at 115℃; for 48h; Dean-Stark; Inert atmosphere; | 95% |
With toluene-4-sulfonic acid In benzene Heating; | |
With toluene-4-sulfonic acid In benzene for 24h; Heating / reflux; | |
With toluene-4-sulfonic acid In toluene at 125℃; | 10.5 g |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil at 23℃; for 16h; Inert atmosphere; | 95% |
Stage #1: 6-bromoindan-1-one; methyl iodide In tetrahydrofuran for 0.25h; Stage #2: With sodium hydride In tetrahydrofuran; water for 2.5h; | 84% |
Stage #1: 6-bromoindan-1-one; methyl iodide In tetrahydrofuran at 20℃; for 0.25h; Stage #2: With sodium hydride In tetrahydrofuran for 2h; | 78.6% |
6-bromoindan-1-one
3,4-(methylenedioxy)-benzeneboronic acid
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; benzene Suzuki coupling; Heating; | 94% |
6-bromoindan-1-one
6-bromo-1,1-dimethyl-2,3-dihydro-1H-indene
Conditions | Yield |
---|---|
Stage #1: With dimethyl zinc(II); titanium tetrachloride In dichloromethane; toluene at -40℃; for 0.333333h; Stage #2: 6-bromoindan-1-one In dichloromethane; toluene at -40 - 20℃; for 18h; | 94% |
6-bromoindan-1-one
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; potassium hydroxide In methanol; water for 3h; Reflux; | 94% |
With hydroxylamine hydrochloride In methanol for 1h; Heating; | |
With pyridine; hydroxylamine hydrochloride In ethanol at 20℃; for 2h; |
6-bromoindan-1-one
(S,E)-N-(1-(4-bromophenyl)ethylidene)-2-methylpropane-2-sulfinamide
C21H23Br2NO2S
Conditions | Yield |
---|---|
Stage #1: 6-bromoindan-1-one With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.666667h; Inert atmosphere; Sealed tube; Stage #2: (S,E)-N-(1-(4-bromophenyl)ethylidene)-2-methylpropane-2-sulfinamide In tetrahydrofuran at -78℃; for 24h; Inert atmosphere; Sealed tube; diastereoselective reaction; | 94% |
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; benzene Suzuki coupling; Heating; | 93% |
6-bromoindan-1-one
(S)-N-((S)-1-((S)-6-bromo-1-oxo-2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide
Conditions | Yield |
---|---|
Stage #1: 6-bromoindan-1-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h; Inert atmosphere; Stage #2: (SS)-2-methyl-N-(2,2,2-trifluoroethylidene)-propane-2-sulfinamide In tetrahydrofuran at -78℃; for 4h; Inert atmosphere; diastereoselective reaction; | 93% |
6-bromoindan-1-one
Conditions | Yield |
---|---|
With potassium carbonate; ruphos; palladium diacetate In water; toluene at 100℃; Suzuki Coupling; Inert atmosphere; Sealed vial; | 90% |
6-bromoindan-1-one
Conditions | Yield |
---|---|
With water; palladium diacetate; potassium carbonate; ruphos In toluene at 100℃; for 6h; Suzuki Coupling; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; benzene Suzuki coupling; Heating; | 89% |
6-bromoindan-1-one
p-methoxybenzyl chloride
Conditions | Yield |
---|---|
Stage #1: 6-bromoindan-1-one With sodium hydride In N,N-dimethyl-formamide at 4 - 23℃; for 1h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 10 - 23℃; for 14h; | 87% |
6-bromoindan-1-one
methylamine
6-bromo-N-methyl-2,3-dihydro-1H-inden-1-amine
Conditions | Yield |
---|---|
Stage #1: 6-bromoindan-1-one; methylamine In methanol at 20℃; for 3.5h; Stage #2: With sodium tetrahydroborate In methanol at 20℃; | 87% |
Stage #1: 6-bromoindan-1-one; methylamine In methanol at 20℃; for 3.5h; Stage #2: With methanol; sodium tetrahydroborate at 20℃; |
6-bromoindan-1-one
2-hydrazinobenzoic acid hydrochloride
Conditions | Yield |
---|---|
In ethanol; water at 20℃; for 1h; | 86% |
6-bromoindan-1-one
dimethyl amine
6-bromo-2,3-dihydro-N,N-dimethyl-1H-inden-1-amine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 120℃; for 0.0833333h; Microwave irradiation; | 85% |
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 120℃; for 0.0833333h; Product distribution / selectivity; Inert atmosphere; Microwave irradiation; | 85% |
Stage #1: 6-bromoindan-1-one; dimethyl amine In 1,2-dichloro-ethane Sealed tube; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 120℃; for 0.0833333h; Product distribution / selectivity; Inert atmosphere; Microwave irradiation; | 85% |
6-bromoindan-1-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; propionic acid In 1,2-dichloro-benzene at 105℃; for 16h; | 84% |
With toluene-4-sulfonic acid; propionic acid In 1,2-dichloro-benzene at 105℃; for 16h; | 84% |
With PPA at 120℃; for 12h; | 24% |
6-bromoindan-1-one
1,3,5-trimethylpyrazole-4-boronic acid pinacol ester
6-(1,3,5-Trimethyl-1 H-pyrazol-4-yl)-indan-1-one
Conditions | Yield |
---|---|
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 100℃; for 3h; | 84% |
Molecular Structure of 1H-Inden-1-one,6-bromo-2,3-dihydro- (CAS NO.14548-39-1):
IUPAC Name: 6-bromo-2,3-dihydroinden-1-one
Empirical Formula: C9H7BrO
Molecular Weight: 211.0553
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 17.07 Å2
Index of Refraction: 1.622
Molar Refractivity: 46.24 cm3
Molar Volume: 131.2 cm3
Surface Tension: 49.9 dyne/cm
Density: 1.608 g/cm3
Flash Point: 111.6 °C
Enthalpy of Vaporization: 53.1 kJ/mol
Boiling Point: 291.6 °C at 760 mmHg
Vapour Pressure: 0.00193 mmHg at 25°C
InChI
InChI=1/C9H7BrO/c10-7-3-1-6-2-4-9(11)8(6)5-7/h1,3,5H,2,4H2
Smiles
c12C(CCc1ccc(c2)Br)=O
Melting point: 111-115 °C(lit.)
Product Categories: Benzocycles; pharmacetical; Pharmaceutical intermediate; C9; Carbonyl Compounds; Ketones
WGK Germany: 3
1H-Inden-1-one,6-bromo-2,3-dihydro- , with CAS number of 14548-39-1, can be called 6-Bromo-2,3-dihydroinden-1-one ; 6-bromo-1-indanone ; 6-bromo-indan-1-one ; 6-bromo indanone ; 6-Bromo-1-indanone,98% ; 6-Brom-2,3-dihydro-1H-inden-1-on .It is a white to yellow crystalline powder or needles.
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