14548-39-1

Basic information

• Product Name: 6-Bromoindanone
• Synonyms: 6-BROMO-2,3-DIHYDROINDEN-1-ONE;6-BROMO-1-INDANONE;6-BROMO-INDAN-1-ONE;6-BROMO INDANONE;6-Bromo-1-indanone,98%;1H-Inden-1-one,6-bromo-2,3-dihydro-;6-bromo-2,3-dihydro-1H-inden-1-one;6-Bromo-2,3-dihydro-1H-inden-1-one, 6-Bromo-2,3-dihydro-1-oxo-1H-indene
• CAS NO: 14548-39-1
• Molecular Formula: C₉H₇BrO
• Molecular Weight: 211.06
• EINECS: 1312995-182-4
• Product Categories: Benzocycles;pharmacetical;Pharmaceutical intermediate;C9;Carbonyl Compounds;Ketones;Indole Derivatives;Miscellaneous Reagents
• Mol File: 14548-39-1.mol
• Article Data: 28

Chemical Properties

• Melting Point: 111-115 °C(lit.)
• Boiling Point: 291.6 ºC at 760 mmHg
• Flash Point: 111.6 ºC
• Appearance: White to yellow/Crystalline Powder or Needles
• Density: 1.608 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Refrigerator
• CAS DataBase Reference: 6-Bromoindanone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromoindanone(14548-39-1)
• EPA Substance Registry System: 6-Bromoindanone(14548-39-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 14548-39-1(Hazardous Substances Data)

Usage

Chemical Properties

White to yellow crystalline powder or needles. Density 1.608g/cm3, melting point 111-115°C(lit.), boiling point 291.6°C at 760mmHg, flash point 111.6°C, refractive index 1.6231, vapor pressure 0.002mmHg at 25°C. 6-Bromoindanone can be used as intermediate in pharmaceutical and chemical synthesis.

Uses

6-Bromo-1-indanone is used as an organic chemical synthesis intermediate.

Preparation

6-Bromoindanone synthesis: Trifluoromethanesulfonic acid (0.35 mL, 4 mmol) was added to anhydrous CHCl3 or CH2Cl2 (2 mL) solution of amide substrate 6 (1 mmol). The mixture was stirred for 4 h and then poured into ice. The product was extracted into CHCl3, and the organic solution was washed with H2O, brine and dried with anhydrous sodium sulfate. The crude product was isolated and purified by column chromatography (hexane:ethyl acetate). Recovery of nitro-substituted aniline: The aqueous extract was made basic by the addition of 10MNaOH and the solution was extracted with CHCl3. The organic solution was washed with H2O, brine (2x) and dried over anhydrous sodium sulfate to yield 6-bromoindanone in 88% yield.

InChI:InChI=1/C9H7BrO/c10-7-3-1-6-2-4-9(11)8(6)5-7/h1,3,5H,2,4H2

Synthetic route

3-(4-bromophenyl)propionic acid (1643-30-7) → 6-bromoindan-1-one (14548-39-1)

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 (62803-47-8) + tert-butyldimethylsilyl chloride (18162-48-6) → 6-bromoindan-1-one (14548-39-1)

Conditions	Yield
With 1H-imidazole In dichloromethane	98%

3-(4-bromophenyl)propanoyl chloride (55394-81-5) → 6-bromoindan-1-one (14548-39-1)

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 (1383443-48-8) → 6-bromoindan-1-one (14548-39-1)

Conditions	Yield
With trifluorormethanesulfonic acid In chloroform at 50℃; for 4h; Friedel Crafts acylation; Inert atmosphere;	88%

6-aminoindan-1-one (69975-65-1) → 6-bromoindan-1-one (14548-39-1)

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 (1643-30-7) → 6-bromoindan-1-one (14548-39-1) + 6-bromo-2-[3-(4-bromophenyl)-1-oxopropyl]-indan-1-one (1610628-81-3)

Conditions	Yield
With trifluorormethanesulfonic acid; trifluoroacetic acid In dichloromethane at 20℃; for 2h;	A 8% B 70%

3-(4-bromophenyl)propionic acid (1643-30-7) → 6-bromoindan-1-one (14548-39-1) + C18H14Br2O2

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 (83-33-0) → 4-bromo-2,3-dihydroinden-1-one (15115-60-3) + 6-bromoindan-1-one (14548-39-1) + 5-Bromo-1-indanone (34598-49-7) + 4,7-dibromo-1-indanone (103515-98-6)

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 (83-33-0) → 4-bromo-2,3-dihydroinden-1-one (15115-60-3) + 6-bromoindan-1-one (14548-39-1) + 5-Bromo-1-indanone (34598-49-7) + 4,6-dibromo-1-indanone

Conditions	Yield
With aluminium trichloride; bromine at 110℃; for 0.5h; Further byproducts given;	A 47% B 21% C 3% D 1%

6-bromo-1H-indene (33065-61-1) → 6-bromoindan-1-one (14548-39-1) + (+)-(1S)-6-bromoinden-1-ol

Conditions	Yield
With Pseudomonas putida UV4 for 7h;	A 28% B 16%

inden-1-one (83-33-0) → 6-bromoindan-1-one (14548-39-1)

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

5-bromo-1H-indene (75476-78-7) → 6-bromoindan-1-one (14548-39-1) + 5-bromo-1,2-dihydroxyindane

Conditions	Yield
With Pseudomonas putida UV4 for 7h;	A 4% B n/a

3-(4-bromophenyl)propionic acid (1643-30-7) → 6-bromoindan-1-one (14548-39-1) + 3-(4-bromo-3-sulfo-phenyl)-propionic acid

Conditions	Yield
With sulfuric acid

inden-1-one (83-33-0) → 4-bromo-2,3-dihydroinden-1-one (15115-60-3) + 6-bromoindan-1-one (14548-39-1)

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

3-(4-bromophenyl)propionic acid (1643-30-7) + sulfuric acid (7664-93-9) → 6-bromoindan-1-one (14548-39-1)

p-bromo-hydrocinnamic acid → 6-bromoindan-1-one (14548-39-1)

Conditions	Yield
With sulfuric acid at 145℃; man giesst auf Eis;

5-(4-bromo-benzyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione (198494-75-6) → 6-bromoindan-1-one (14548-39-1)

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

4-bromo-benzaldehyde (1122-91-4) + LiPh2InH2 → 6-bromoindan-1-one (14548-39-1)

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 (1200-07-3, 5676-63-1, 17916-60-8) → 6-bromoindan-1-one (14548-39-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2 / Pd/C / methanol 2: (COCl)2 / CH2Cl2 3: aluminum trichloride / CH2Cl2 View Scheme

4-bromo-benzaldehyde (1122-91-4) + (S)-(Fmoc-amino)-(4-fluoro-phenyl)-acetic acid on Wang resin → 6-bromoindan-1-one (14548-39-1)

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 (34598-49-7) → 6-bromoindan-1-one (14548-39-1)

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 (34598-50-0) → 6-bromoindan-1-one (14548-39-1)

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 (75476-86-7) → 6-bromoindan-1-one (14548-39-1)

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 (70146-78-0) → 6-bromoindan-1-one (14548-39-1)

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 (92013-18-8) → 6-bromoindan-1-one (14548-39-1)

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 (589-15-1) → 6-bromoindan-1-one (14548-39-1)

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 (3650-78-0, 71205-17-9, 84878-00-2) → 6-bromoindan-1-one (14548-39-1)

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 (75567-84-9) → 6-bromoindan-1-one (14548-39-1)

Conditions	Yield
With trifluorormethanesulfonic acid at 25℃; Cooling with ice;

6-nitroindan-1-one (24623-24-3) → 6-bromoindan-1-one (14548-39-1)

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 (14548-39-1) → 6-Bromo-2,3-dihydro-1H-inden-1-ol (75476-86-7)

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 (14548-39-1) + N-4-chlorophenylhydrazine (1073-69-4) → N-(6-Bromo-indan-1-ylidene)-N'-(4-chloro-phenyl)-hydrazine

Conditions	Yield
With acetic acid In ethanol for 0.5h; Heating / reflux;	100%

6-bromoindan-1-one (14548-39-1) + phenylboronic acid (98-80-6) → 6-phenyl-1-indanone (170497-64-0)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; benzene Suzuki coupling; Heating;	99%

6-bromoindan-1-one (14548-39-1) + dimethyl zinc(II) (544-97-8) → 6-bromo-1,1-dimethyl-2,3-dihydro-1H-indene (67159-88-0)

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%

methanesulfonamide (3144-09-0) + 6-bromoindan-1-one (14548-39-1) → C10H11NO3S

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%

6-bromoindan-1-one (14548-39-1) + potassium isopropenyltrifluoroborane → C12H12O

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 (14548-39-1) + bis(pinacol)diborane (73183-34-3) → 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H-inden-1-one (915402-06-1)

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 (14548-39-1) + Methyltriphenylphosphonium bromide (1779-49-3) → 6-bromo-1-methylenyl-2,3-dihydro-1H-indene

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 (14548-39-1) + ethylene glycol (107-21-1) → 6‘-bromo-2‘,3‘-dihydrospiro[[1,3]dioxolane-2,1‘-indene] (866848-94-4)

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

6-bromoindan-1-one (14548-39-1) + methyl iodide (74-88-4) → 6-bromo-2,2-dimethyl-2,3-dihydro-1H-inden-1-one

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 (14548-39-1) + 3,4-(methylenedioxy)-benzeneboronic acid (94839-07-3) → 6-benzo[1,3]dioxo-5-ylindan-1-one

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; benzene Suzuki coupling; Heating;	94%

6-bromoindan-1-one (14548-39-1) → 6-bromo-1,1-dimethyl-2,3-dihydro-1H-indene (67159-88-0)

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 (14548-39-1) → 6-bromo-2,3-dihydro-1H-inden-1-one oxime

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 (14548-39-1) + (S,E)-N-(1-(4-bromophenyl)ethylidene)-2-methylpropane-2-sulfinamide (1039750-63-4) → C21H23Br2NO2S (1616493-88-9)

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%

6-bromoindan-1-one (14548-39-1) + 4-biphenylboronic acid (5122-94-1) → 6-biphenyl-4-ylindan-1-one

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; benzene Suzuki coupling; Heating;	93%

(SS)-2-methyl-N-(2,2,2-trifluoroethylidene)-propane-2-sulfinamide + 6-bromoindan-1-one (14548-39-1) → (S)-N-((S)-1-((S)-6-bromo-1-oxo-2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide (1556948-49-2)

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 (14548-39-1) + trans-2-(trifluoromethyl)cyclopropylboronic acid MIDA ester → trans-6-(2-(trifluoromethyl)cyclopropyl)-2,3-dihydro-1H-inden-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 (14548-39-1) + trans-2-(trifluoromethyl)cyclopropylboronic diester of N-methyliminodiacetic acid → trans-6-(2-(trifluoromethyl)cyclopropyl)-2,3-dihydro-1H-inden-1-one

Conditions	Yield
With water; palladium diacetate; potassium carbonate; ruphos In toluene at 100℃; for 6h; Suzuki Coupling; Inert atmosphere;	90%

thiophene boronic acid (6165-68-0) + 6-bromoindan-1-one (14548-39-1) → 6-thiophen-2-ylindan-1-one

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; benzene Suzuki coupling; Heating;	89%

6-bromoindan-1-one (14548-39-1) + p-methoxybenzyl chloride (824-94-2) → 6-bromo-1-((4-methoxybenzyl)oxy)-2,3-dihydro-1H-indene

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 (14548-39-1) + methylamine (74-89-5) → 6-bromo-N-methyl-2,3-dihydro-1H-inden-1-amine (371251-07-9)

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 (14548-39-1) + 2-hydrazinobenzoic acid hydrochloride (33906-30-8, 52356-01-1) → o-[(2,3-dihydro-6-bromoinden-3-ylidene)hydrazino]-benzoic acid

Conditions	Yield
In ethanol; water at 20℃; for 1h;	86%

6-bromoindan-1-one (14548-39-1) + dimethyl amine (124-40-3) → 6-bromo-2,3-dihydro-N,N-dimethyl-1H-inden-1-amine (371249-89-7)

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 (14548-39-1) → 3,8,13-tribromo-10,15-dihydro-5H-diindeno[1,2-a:1',2'-c]fluorene

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 (14548-39-1) + 1,3,5-trimethylpyrazole-4-boronic acid pinacol ester (844891-04-9) → 6-(1,3,5-Trimethyl-1 H-pyrazol-4-yl)-indan-1-one (1096520-73-8)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 100℃; for 3h;	84%

Upstream product

• 1643-30-7 3-(4-bromophenyl)propionic acid 
• 55394-81-5 3-(4-bromophenyl)propanoyl chloride 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 83-33-0 inden-1-one 
• 62803-47-8 6-hydroxy-1-indanone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 69975-65-1 6-aminoindan-1-one 
• 24623-24-3 6-nitroindan-1-one 
• 75567-84-9 methyl 3-(4-bromopehynl)propanoate 
• 3650-78-0 methyl 4-bromocinnamate 
• 1383443-48-8 C₁₅H₁₃BrN₂O₃ 
• 92013-18-8 2-[(4-bromophenyl)methyl]propanedioic acid 
• 70146-78-0 diethyl 2-(4-bromobenzyl)malonate 
• 75476-86-7 6-Bromo-2,3-dihydro-1H-inden-1-ol 

Downstream Products

• 6968-28-1 4-bromophthalic acid 
• 75476-86-7 6-Bromo-2,3-dihydro-1H-inden-1-ol 
• 170497-64-0 6-phenylindan-1-one 
• 866848-94-4 6‘-bromo-2‘,3‘-dihydrospiro[[1,3]dioxolane-2,1‘-indene] 
• 417699-00-4 3-bromo-6-phenylinden-1-one 
• 67159-88-0 6-bromo-2,3-dihydro-1,1-dimethyl-1H-indene 
• 1334709-20-4 (E)-6-bromo-2-[4-(dimethylamino)benzylidene]indan-1-one 
• 1334709-25-9 (E)-2-[4-(dimethylamino)benzylidene]-6-(tributylstannyl)indan-1-one 
• 1383982-64-6 (1r,1’R,4R)-4-methoxy-5”-methyl-6’-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3’H-dispiro[cyclohexane-1,2’-indene-1’2”-imidazol]-4”-amine 
• 1411981-02-6 2-(pyrimidin-2-ylmethyl)-7-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-1(2H)-one 
• 1411980-86-3 2-(pyrimidin-2-ylmethyl)-7-(4-(trifluoromethoxy)phenyl)-3,4-dihydroisoquinolin-1(2H)-one 

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