606-23-5

Basic information

• Product Name: 1,3-Indanedione
• Synonyms: 1,3-DIOXOINDANE;1,3-DIKETOHYDRINDENE;1,3-HYDRINDENEDIONE;1,3-INDANDIONE;1,3-INDANEDIONE;AURORA KA-7365;DIKETOHYDRINDENE;1,3-Indanone
• CAS NO: 606-23-5
• Molecular Formula: C₉H₆O₂
• Molecular Weight: 146.14
• EINECS: 210-109-7
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 606-23-5.mol
• Article Data: 44

Chemical Properties

• Melting Point: 129-132 °C(lit.)
• Boiling Point: 205.74°C (rough estimate)
• Flash Point: 113 °C
• Appearance: White to yellow to beige/Powder
• Density: 1,37 g/cm3
• Vapor Pressure: 0.000191mmHg at 25°C
• Refractive Index: 1.5049 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 8.95±0.20(Predicted)
• Water Solubility: Soluble in ethanol, ether, benzene, slightly soluble in water.
• BRN: 1210061
• CAS DataBase Reference: 1,3-Indanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Indanedione(606-23-5)
• EPA Substance Registry System: 1,3-Indanedione(606-23-5)

Safety Data

• Hazard Codes: Xi
• Statements: 33-36/37/38
• Safety Statements: 24/25-36/37/39-27-26
• WGK Germany: 3
• RTECS: NK5070000
• TSCA: Yes
• Hazardous Substances Data: 606-23-5(Hazardous Substances Data)

Usage

Uses

It is used in the first stage of forensic identification of latent fingerprints. It is particularly useful for paper, and for items printed with thermal inks such as receipts.

Definition

ChEBI: A member of the class of indanones that is indane in which the hydrogens at positions 2 and 4 have been replaced by oxo groups.

Purification Methods

Recrystallise it from EtOH or *C6H6. In dilute alkali it gives a deep yellow solution of the enol. [Bernasconi & Paschalis J Am Chem Soc 108 2969 1986]. [Beilstein 7 IV 2344.]

InChI:InChI=1/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-5,10H

Synthetic route

(-)-trans-(1R,3R)-1,3-Dihydroxyindane → 1H-indene-1,3(2H)-dione (606-23-5) + (R)-3-hydroxy-2,3-dihydro-1H-inden-1-one

Conditions	Yield
With Shvo's Catalyst In acetone at 35℃; for 20h; Air;	A n/a B 95%

3-hydroxy-2,3-dihydro-1H-inden-1-one (26976-59-0) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
With Jones reagent In acetone at 20℃; for 2h;	95%

2,3-dihydro-1H-indene-1,3-diol (60414-82-6) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
With trifluorormethanesulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In 1,4-dioxane at 20℃; for 0.333333h;	92%

benzoyl chloride (98-88-4) + malonoyl dichloride (1663-67-8) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
With aluminium trichloride In nitrobenzene at 80℃; for 5h; Mechanism; other aromatic acyl chlorides;	90%
With aluminium trichloride In nitrobenzene at 80℃; for 5h;	90%

3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide (117560-06-2) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
In acetonitrile for 1h; Heating;	90%

phthalic acid dimethyl ester (131-11-3) + ethyl acetate (141-78-6) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
Stage #1: phthalic acid dimethyl ester; ethyl acetate With sodium methylate at 12 - 80℃; Large scale; Stage #2: With hydrogenchloride In water at 45 - 55℃; for 5h; Large scale;	83.2%

1-Indanol (6351-10-6) → 1H-indene-1,3(2H)-dione (606-23-5) + inden-1-one (83-33-0)

Conditions	Yield
With manganese(III) Schiff-base; dihydrogen peroxide at 20℃; for 5h;	A 14% B 83%
With C26H30F6MnN6O6S2; dihydrogen peroxide; acetic acid In acetonitrile at 20℃; for 1h; chemoselective reaction;	A 9% B 61%

phthalic acid dimethyl ester (131-11-3) + acetic acid (64-19-7) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
Stage #1: phthalic acid dimethyl ester; acetic acid With sodium methylate at 12 - 80℃; Stage #2: With hydrogenchloride In water at 45 - 55℃; for 5h;	82.7%

1-oxo-1H-inden-3-yl pivalate + dimethyl 2,2-di(but-2-yn-1-yl)malonate (107428-05-7) → 1H-indene-1,3(2H)-dione (606-23-5) + dimethyl 4,10-dimethyl-9-oxo-3,9-dihydrocyclopenta[b]fluorene-2,2(1H)-dicarboxylate

Conditions	Yield
With calcium hydride; 1,5-hexadienerhodium(I)-chloride dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 80℃; for 15h; Schlenk technique; Inert atmosphere;	A 10% B 76%

INDANE (496-11-7) → 1H-indene-1,3(2H)-dione (606-23-5) + 1-Indanol (6351-10-6) + inden-1-one (83-33-0)

Conditions	Yield
With sodium percarbonate; adogen 464; bis-(tributyltin oxide) dioxochromium(VI); toluene-4-sulfonic acid In acetonitrile at 80 - 83℃; for 20h;	A 4% B 5% C 70%
With sodium percarbonate; adogen 464; bis-(tributyltin oxide) dioxochromium(VI) In acetonitrile at 80 - 83℃; for 20h; Product distribution; benzylic oxidation with various reagents, solvent dependence;	A 2% B 10% C 60%
With dipyridinium dichromate; sodium percarbonate; adogen 464 In 1,2-dichloro-ethane at 80 - 83℃; for 20h;	A 6% B 7% C 30%

INDANE (496-11-7) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
With tert.-butylnitrite; N-hydroxyphthalimide In acetonitrile at 80℃; for 24h; Schlenk technique;	61%
With tert.-butylnitrite; N-hydroxyphthalimide; oxygen In acetonitrile at 80℃; under 760.051 Torr; for 24h; Schlenk technique;	61%

2-(9-xanthylidene)indane-1,3-dione (1807-62-1) → 1H-indene-1,3(2H)-dione (606-23-5) + 2-(9-xanthyl)indane-1,3-dione (87688-44-6)

Conditions	Yield
With thiophenol at 100℃; for 10h; Product distribution; other reagent;	A 12% B 55%

dimethyl 2,2-di(but-2-yn-1-yl)malonate (107428-05-7) + 1-oxo-1H-inden-3-yl acetate → 1H-indene-1,3(2H)-dione (606-23-5) + dimethyl 4,10-dimethyl-9-oxo-3,9-dihydrocyclopenta[b]fluorene-2,2(1H)-dicarboxylate + dimethyl-3-(1-acetoxyethylidene)-4-ethylidenecyclopentane-1,1-dicarboxylate

Conditions	Yield
With silver tetrafluoroborate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; calcium hydride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 80℃; Schlenk technique; Inert atmosphere;	A 27% B 14% C 45%
With calcium hydride; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 80℃; Reagent/catalyst; Schlenk technique; Inert atmosphere;	A 27% B 32% C 40%
With calcium hydride; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 80℃; Schlenk technique; Inert atmosphere;	A 10% B 39% C 12%

INDANE (496-11-7) → 1H-indene-1,3(2H)-dione (606-23-5) + inden-1-one (83-33-0)

Conditions	Yield
With dipyridinium dichromate; adogen 464; dihydrogen peroxide; sodium carbonate In various solvent(s) for 24h; Oxidation; Heating;	A 18% B 38%

C18H17NO2 → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere;	35%

2-propylindan-1,3-dione (14570-43-5) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
In acetonitrile for 4h; UV-irradiation;	28%

INDANE (496-11-7) → 1H-indene-1,3(2H)-dione (606-23-5) + 3-hydroxy-2,3-dihydro-1H-inden-1-one (26976-59-0) + inden-1-one (83-33-0)

Conditions	Yield
With tert.-butylhydroperoxide; [(pymox-Me2)2RuCl2]+BF4- In water at 20℃; for 2h;	A 5% B n/a C n/a

2-formylindane-1,3-dione (2740-22-9) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
With hydrogenchloride

2-bromo-indan-1,3-dione (7319-63-3) → 1H-indene-1,3(2H)-dione (606-23-5) + 2,2-dibromo-indan-1,3-dione (1685-97-8)

Conditions	Yield
With water

[2,2']biindenyl-1,3,1',3'-tetraone (6940-95-0) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
With dihydrogen peroxide Uebersaettigen der Loesung mit Schwefelsaeure;

2,2-bis-(1,3-dioxo-indan-2-yl)-acenaphthen-1-one (103165-42-0) → 1H-indene-1,3(2H)-dione (606-23-5) + 2-(2-oxo-acenaphthen-1-ylidene)-indan-1,3-dione (850645-51-1)

Conditions	Yield
With sulfuric acid

3-methoxy-1-oxo-indene-2-carboxylic acid ethyl ester (87768-18-1) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
at 100℃;

2-bromo-1,3-dioxo-indan-2-carboxylic acid ethyl ester (74307-85-0) → 1H-indene-1,3(2H)-dione (606-23-5) + 2,2-dibromo-indan-1,3-dione (1685-97-8)

Conditions	Yield
With water

ethyl 3-amino-1-oxo-1H-indene-2-carboxylate + furan-2,3,5(4H)-trione pyridine (1:1) → 1H-indene-1,3(2H)-dione (606-23-5)

1-(1,3-dioxo-indan-2-yl)-4-(1,3-dioxo-indan-2-ylidene)-3,4-dihydro-2H-pyrrolium betaine (15365-99-8) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
at 210 - 220℃; under 0.1 Torr;

2‑(2‑hydroxybenzylidene)‑1H‑indene‑1,3(2H)‑dione (25299-18-7) + phenylhydrazine (100-63-0) → 1H-indene-1,3(2H)-dione (606-23-5) + salicylaldehyde (90-02-8)

vinyl acetate (108-05-4) + Phthaloyl dichloride (88-95-9) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
With aluminium trichloride

3-methylidenephthalide (3453-63-2) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
at 1100℃; Mechanism; lower temperature;
at 1100℃; flash thermolysis; Yield given;
With potassium tert-butylate In tetrahydrofuran

2-diazo-3-hydroxy-1-indanone (28164-53-6) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
tin(ll) chloride In dichloromethane Ambient temperature;

1,3-indandione anion (19968-95-7) → 1H-indene-1,3(2H)-dione (606-23-5)

Conditions	Yield
With 4-chlorobenzylmalononitrile; potassium chloride In water; dimethyl sulfoxide at 20℃; Rate constant; var. phenyl-substituted benzylmalononitriles;

1H-indene-1,3(2H)-dione (606-23-5) → 2-bromo-indan-1,3-dione (7319-63-3)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide; potassium bromide In toluene at 20℃; for 0.5h;	100%
With hydroxy(tosyloxy)iodobenzene; copper(ll) bromide In acetonitrile at 0℃; for 0.0833333h;	90%
With bromomalononitrile In N,N-dimethyl-formamide at 20℃; for 0.5h; Reagent/catalyst;	90%

1H-indene-1,3(2H)-dione (606-23-5) + 2-aminoacetophenone (551-93-9) → 10-methyl-11H-indeno[1,2-b]quinolin-11-one (142790-83-8)

Conditions	Yield
With acetic acid at 130℃; for 4h;	100%
With malic acid In neat (no solvent) at 70℃; for 2.4h; Friedlaender Quinoline Synthesis; Green chemistry;	81%
With water; acetic acid at 130℃; for 4h;	50%

1H-indene-1,3(2H)-dione (606-23-5) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → (Z)-2-(3,5-di-tert-butyl-4-hydroxybenzylidene)-1H-indene-1,3(2H)-dione (53566-09-9)

Conditions	Yield
With toluene-4-sulfonic acid In chloroform for 21h; Knoevenagel reaction; Heating;	100%
With sulfuric acid In acetic acid for 51h; Ambient temperature;	75%
With piperidine In ethanol for 8h; Knoevenagel Condensation; Reflux;	51.5%
With piperidine In acetic acid

1H-indene-1,3(2H)-dione (606-23-5) + (Z)-5a,6,7,9a-Tetrahydro-5a,6-tetramethylene-11-[ethoxycarbonyl(nitro)methylene]naphtho[1',2':4,5]imidazo[1,2-a]pyridine (234762-41-5) → C40H30N2O2

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; methylene exchange;	100%

1H-indene-1,3(2H)-dione (606-23-5) + 4-chlorobenzaldehyde (104-88-1) + (E)-benzalacetone (1896-62-4) → 2-(4-chlorophenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions	Yield
Stage #1: 1H-indene-1,3(2H)-dione; 4-chlorobenzaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction;	100%

1H-indene-1,3(2H)-dione (606-23-5) + 1-naphthaldehyde (66-77-3) + (E)-benzalacetone (1896-62-4) → 2-(naphthalen-1-yl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions	Yield
Stage #1: 1H-indene-1,3(2H)-dione; 1-naphthaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction;	100%

1H-indene-1,3(2H)-dione (606-23-5) + 4-hydroxy-benzaldehyde (123-08-0) + (E)-benzalacetone (1896-62-4) → 2-(4-hydroxyphenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions	Yield
Stage #1: 1H-indene-1,3(2H)-dione; 4-hydroxy-benzaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction;	100%

1H-indene-1,3(2H)-dione (606-23-5) + 4-cyanobenzaldehyde (105-07-7) + (E)-benzalacetone (1896-62-4) → 2-(4-cyanophenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions	Yield
Stage #1: 1H-indene-1,3(2H)-dione; 4-cyanobenzaldehyde With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction;	100%

1H-indene-1,3(2H)-dione (606-23-5) + (E)-benzalacetone (1896-62-4) + methyl 4-formylbenzoate (1571-08-0) → 2-[4-(methoxycarbonyl)phenyl]-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions	Yield
Stage #1: 1H-indene-1,3(2H)-dione; methyl 4-formylbenzoate With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction;	100%

1H-indene-1,3(2H)-dione (606-23-5) + 3-nitro-benzaldehyde (99-61-6) → 3′-(3-nitrophenyl)dispiro[indene-2,1′-cyclopropane-2′,2′′-indene]-1,1′′,3,3′′-tetraone (18691-32-2)

Conditions	Yield
With bromocyane; triethylamine In methanol at 0 - 20℃; for 0.00416667h; Sealed tube;	100%
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; sodium acetate In ethanol at 20℃; for 0.0333333h; Reagent/catalyst;	96%
With dmap; iodine at 20℃; for 1h; Neat (no solvent); Mechanical ball-milling; chemospecific reaction;	88%

1H-indene-1,3(2H)-dione (606-23-5) + 4-nitrobenzaldehdye (555-16-8) → 3'-(4-nitrophenyl)-dispiro[indan-2,1'-cyclopropane-2',2''-indan]-1,1'',3,3''-tetrone (18691-31-1)

Conditions	Yield
With bromocyane; triethylamine In methanol at 0 - 20℃; for 0.00416667h; Sealed tube;	100%
With dmap; iodine at 20℃; for 1h; Neat (no solvent); Mechanical ball-milling; chemospecific reaction;	89%

1H-indene-1,3(2H)-dione (606-23-5) + 2,4-dichlorobenzaldeyhde (874-42-0) → 3′-(2,4-dichlorophenyl)dispiro[indene-2,1′-cyclopropane-2′,2′′-indene]-1,1′′,3,3′′-tetraone (7090-75-7)

Conditions	Yield
With bromocyane; triethylamine In methanol at 0 - 20℃; for 0.00416667h; Sealed tube;	100%
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; sodium acetate In ethanol at 20℃; for 0.166667h; Reagent/catalyst;	96%

formaldehyd (50-00-0) + 1H-indene-1,3(2H)-dione (606-23-5) → dispiro[indene-2,1'-cyclopropane-2',2''-indene]-1,1'',3,3''-tetraone (106144-67-6)

Conditions	Yield
With bromocyane; sodium ethanolate In methanol at 0 - 20℃; for 0.00416667h; Sealed tube;	100%

4-hydroxy-3-ethoxybenzaldehyde (121-32-4) + 1H-indene-1,3(2H)-dione (606-23-5) → 2-(3-ethoxy-4-hydroxybenzylidene)-1H-indene-1,3(2H)-dione

Conditions	Yield
With hydrogenchloride; acetic acid In water at 20℃; Inert atmosphere;	99.8%

1H-indene-1,3(2H)-dione (606-23-5) + 4-nitrobenzaldehdye (555-16-8) → 2-(p-nitrobenzylidene)indan-1,3-dione (15875-60-2)

Conditions	Yield
With L-proline In methanol at 25℃; for 12h; organocatalytic Knoevenagel condensation;	99%
In water at 20 - 80℃; Knoevenagel condensation;	97.5%
With magnesium oxide at 20℃; for 0.333333h; Knoevenagel condensation;	94%

1H-indene-1,3(2H)-dione (606-23-5) + 2,5-dimethoxybenzaldehyde (93-02-7) → 2-(2,5-dimethoxybenzylidene)-1H-indene-1,3(2H)-dione (67200-96-8)

Conditions	Yield
With hydrogenchloride; acetic acid In ethanol; water at 50 - 60℃; Reagent/catalyst; Solvent;	99%
Stage #1: 1H-indene-1,3(2H)-dione With pyridine Stage #2: 2,5-dimethoxybenzaldehyde at 100℃; for 1h;	75%
With ethanol

1H-indene-1,3(2H)-dione (606-23-5) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 2-(2,4-dihydroxybenzylidene)-1H-indene-1,3(2H)-dione (78426-08-1)

Conditions	Yield
With pyridine In ethanol Reflux;	99%
In ethanol for 3h; Heating;	72%
With hydrogenchloride; acetic acid In water at 20℃; Inert atmosphere;	43.1%
With piperidine; ethanol
With potassium hydroxide bei der Kondensation;

1H-indene-1,3(2H)-dione (606-23-5) + propargyl bromide (106-96-7) → 2,2-di(prop-2-yn-1-yl)-1H-indene-1,3(2H)-dione (24241-98-3)

Conditions	Yield
With caesium carbonate In acetone; toluene at 20℃; for 16h;	99%
With potassium hydroxide In water; acetone at 2440℃; for 16h; Reflux;	93%
With potassium hydroxide In water at 40℃; for 24h;	93%

1H-indene-1,3(2H)-dione (606-23-5) + C22H22O5 → poly{oxy[(E)-but-2-enylene](1,3-indandione-2,2-diyl)[(E)-but-2-enylene]}, Mn=14000; monomer(s): (2Z,7Z)-non-2,7-diene-5-oxa-1,9-ol dibenzoic acid ester; 1,3-indane-2,4-diene

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; tris(dibenzylideneacetone)dipalladium (0); 1,4-di(diphenylphosphino)-butane In dichloromethane; N,N-dimethyl-formamide Tsuji-Trost reaction;	99%

1H-indene-1,3(2H)-dione (606-23-5) + allyl alcohol (107-18-6) → 2,2-diallyl-1H-indene-1,3(2H)-dione (81055-89-2)

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In water; ethyl acetate at 20℃; for 18h; Tsuji-Trost reaction;	99%
With Ru(Cp*)(η3-C3H5)(p-CH3C6H5SO3)2 In dichloromethane; acetonitrile at 50℃; for 3h; regioselective reaction;	89%

1H-indene-1,3(2H)-dione (606-23-5) + benzaldehyde (100-52-7) → 2-benzyl-indan-1,3-dione (890-44-8)

Conditions	Yield
With 1,2-diamino-benzene; rac-Pro-OH In ethanol at 25℃; for 1h;	99%
With 2,6-dimethyl-1,4-dihydropyrimidine-3,5-dicarboxylic acid diethyl ester; L-proline In ethanol at 25℃; Knoevenagel/hydrogenation reaction;	88%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; L-proline In ethanol at 25℃; for 26h; cascade Knoevenagel olefination/hydrogenation reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction;	88%

1H-indene-1,3(2H)-dione (606-23-5) + benzene (71-43-2) → 3,3-diphenyl-indan-1-one (55010-17-8)

Conditions	Yield
With trifluorormethanesulfonic acid at 20℃; for 24h;	99%

3-(4-bromophenylamino)-5,5-dimethylcyclohex-2-enone (106518-84-7) + 1H-indene-1,3(2H)-dione (606-23-5) + 2-chloro-benzaldehyde (89-98-5) → 10-(4-bromophenyl)-5-(2-chlorophenyl)-7,8-dihydro-7,7-dimethyl-5H-indeno[1,2-b]quinolin-9,11(6H,10H)-dione (1009033-46-8)

Conditions	Yield
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 90℃; for 8h;	99%

1H-indene-1,3(2H)-dione (606-23-5) + 5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one (18940-21-1) + 2-nitro-benzaldehyde (552-89-6) → 7,8-dihydro-7,7-dimethyl-5-(2-nitrophenyl)-10-phenyl-5H-indeno[1,2-b]quinolin-9,11(6H,10H)-dione (1009033-44-6)

Conditions	Yield
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 90℃; for 6h;	99%

(5-methyl-pyridin-2-yl)amine (1603-41-4) + 1H-indene-1,3(2H)-dione (606-23-5) + pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) → 5-(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-5-hydroxypyrimidine-2,4,6(1H,3H,5H)-trione 2-amino-5-methylpyridinium salt (1367748-11-5)

Conditions	Yield
In chloroform for 1h; Reflux;	99%

1H-indene-1,3(2H)-dione (606-23-5) + thieno[3,2-b]thiophene-2-carbaldehyde (31486-86-9) → C16H8O2S2

Conditions	Yield
With aluminum oxide In dichloromethane at 25℃; for 12h; Knoevenagel Condensation;	99%

1H-indene-1,3(2H)-dione (606-23-5) + 2-Formylthieno<2,3-b>thiophene (31486-85-8) → C16H8O2S2

Conditions	Yield
With aluminum oxide In dichloromethane at 25℃; for 12h; Knoevenagel Condensation;	99%

1H-indene-1,3(2H)-dione (606-23-5) + 1-benzyl-4-(pyrrolidin-1-yl)indoline-2,3-dione → 4-benzyl-4,5a,6a,7,8,9-hexahydro-5H-spiro[dipyrrolo[1,2-a:4′,3′,2′-de]quinoline-6,2′-indene]-1′,3′,5-trione

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 60℃; for 12h; Solvent; Molecular sieve; diastereoselective reaction;	99%

1H-indene-1,3(2H)-dione (606-23-5) + 1-(2-chlorobenzyl)-4-(pyrrolidin-1-yl)indoline-2,3-dione → 4-(2-chlorobenzyl)-4,5a,6a,7,8,9-hexahydro-5H-spiro[dipyrrolo-[1,2-a:4′,3′,2′-de]quinoline-6,2′-indene]-1′,3′,5-trione

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 60℃; for 12h; Molecular sieve; diastereoselective reaction;	99%

1H-indene-1,3(2H)-dione (606-23-5) + 1-(4-bromophenyl)-4-(4-chlorophenyl)but-3-yne-1,2-dione → 2-(5-(4-bromophenyl)-2-(4-chlorophenyl)-5-hydroxy-1',3'-dioxo-1',3'-dihydrospiro[cyclopent[2]ene-1,2'-inden]-4-ylidene)-1H-indene-1,3(2H)-dione

Conditions	Yield
With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique;	99%

Upstream product

• 2740-22-9 2-formylindane-1,3-dione 
• 87768-18-1 3-methoxy-1-oxo-indene-2-carboxylic acid ethyl ester 
• 74307-85-0 2-bromo-1,3-dioxo-indan-2-carboxylic acid ethyl ester 
• 108-05-4 vinyl acetate 
• 88-95-9 Phthaloyl dichloride 
• 1807-62-1 2-(9-xanthylidene)indane-1,3-dione 
• 98-88-4 benzoyl chloride 
• 1663-67-8 malonoyl dichloride 
• 160246-88-8 2-iodo-3-phenoxy-1,4-naphthoquinone 
• 496-11-7 INDANE 
• 7664-93-9 sulfuric acid 
• 897-38-1 1,3-Dihydro-3-oxo-2-isobenzofuranylidenmalonsaeurediethylester 
• 5381-33-9 2-benzylidene-indan-1,3-dione 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 824428-86-6 2,2''-benzylidene-bis-[1,2']biindenylidene-3,1',3'-trione 
• 1707-95-5 bindone 
• 29874-41-7 2-(2-furylmethylene)indane-1,3-dione 
• 24760-36-9 2-(thiophen-2-ylmethylene)indan-1,3-dione 
• 24808-79-5 (E)-2-(3-phenylprop-2-en-1-ylidene)indane-1,3-dione 
• 1133-72-8 2-acetyl-indan-1,3-dione 
• 15875-51-1 2-(4-methyl-benzylidene)-indan-1,3-dione 
• 15875-56-6 2-(2-chloro-benzylidene)-indan-1,3-dione 
• 25116-35-2 2-(naphthalen-1-ylmethylene)-1H-indene-1,3(2H)-dione 
• 15875-60-2 2-(p-nitrobenzylidene)indan-1,3-dione 
• 68063-22-9 11-(4-nitro-phenyl)-diindeno[1,2-b;2',1'-e]pyridine-10,12-dione 
• 91158-87-1 2,2-dibenzyl-2,3-dihydro-1H-indene-1,3-dione 
• 328021-61-0 11-(2-hydroxy-phenyl)-diindeno[1,2-b;2',1'-e]pyridine-10,12-dione 
• 25299-18-7 2?(2?hydroxybenzylidene)?1H?indene?1,3(2H)?dione 

Relevant articles and documents

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