Product Name

  • Name

    1,3-Indanedione

  • EINECS 210-109-7
  • CAS No. 606-23-5
  • Article Data80
  • CAS DataBase
  • Density 1.31 g/cm3
  • Solubility Soluble in ethanol, ether, benzene, slightly soluble in water.
  • Melting Point 129-132 °C
  • Formula C9H6O2
  • Boiling Point 302.5 °C at 760 mmHg
  • Molecular Weight 146.145
  • Flash Point 113 °C
  • Transport Information
  • Appearance Yellow to green fine crystalline powder
  • Safety 24/25-36/37/39-27-26
  • Risk Codes 33-36/37/38
  • Molecular Structure Molecular Structure of 606-23-5 (1,3-Indanedione)
  • Hazard Symbols IrritantXi
  • Synonyms 1,3-Diketohydrindene;1,3-Indandione;3-hydroxyinden-1-one;1H-indene-1,3(2H)-dione;1H-Indene-1, 3 (2H)-dione;indan-1,3-dione;indene-1,3-dione;1,3-Indanedione 97%;
  • PSA 34.14000
  • LogP 1.45570

Synthetic route

(-)-trans-(1R,3R)-1,3-Dihydroxyindane

(-)-trans-(1R,3R)-1,3-Dihydroxyindane

A

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

1H-indene-1,3(2H)-dione

B

(R)-3-hydroxy-2,3-dihydro-1H-inden-1-one

(R)-3-hydroxy-2,3-dihydro-1H-inden-1-one

Conditions
ConditionsYield
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

3-hydroxy-2,3-dihydro-1H-inden-1-one

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
With Jones reagent In acetone at 20℃; for 2h;95%
2,3-dihydro-1H-indene-1,3-diol
60414-82-6

2,3-dihydro-1H-indene-1,3-diol

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

benzoyl chloride

malonoyl dichloride
1663-67-8

malonoyl dichloride

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
In acetonitrile for 1h; Heating;90%
phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

ethyl acetate
141-78-6

ethyl acetate

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

1-Indanol

A

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

1H-indene-1,3(2H)-dione

B

inden-1-one
83-33-0

inden-1-one

Conditions
ConditionsYield
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

phthalic acid dimethyl ester

acetic acid
64-19-7

acetic acid

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

1-oxo-1H-inden-3-yl pivalate

dimethyl 2,2-di(but-2-yn-1-yl)malonate
107428-05-7

dimethyl 2,2-di(but-2-yn-1-yl)malonate

A

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

1H-indene-1,3(2H)-dione

B

dimethyl 4,10-dimethyl-9-oxo-3,9-dihydrocyclopenta[b]fluorene-2,2(1H)-dicarboxylate

dimethyl 4,10-dimethyl-9-oxo-3,9-dihydrocyclopenta[b]fluorene-2,2(1H)-dicarboxylate

Conditions
ConditionsYield
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

INDANE

A

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

1H-indene-1,3(2H)-dione

B

1-Indanol
6351-10-6

1-Indanol

C

inden-1-one
83-33-0

inden-1-one

Conditions
ConditionsYield
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

INDANE

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

2-(9-xanthylidene)indane-1,3-dione

A

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

1H-indene-1,3(2H)-dione

B

2-(9-xanthyl)indane-1,3-dione
87688-44-6

2-(9-xanthyl)indane-1,3-dione

Conditions
ConditionsYield
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

dimethyl 2,2-di(but-2-yn-1-yl)malonate

1-oxo-1H-inden-3-yl acetate

1-oxo-1H-inden-3-yl acetate

A

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

1H-indene-1,3(2H)-dione

B

dimethyl 4,10-dimethyl-9-oxo-3,9-dihydrocyclopenta[b]fluorene-2,2(1H)-dicarboxylate

dimethyl 4,10-dimethyl-9-oxo-3,9-dihydrocyclopenta[b]fluorene-2,2(1H)-dicarboxylate

C

dimethyl-3-(1-acetoxyethylidene)-4-ethylidenecyclopentane-1,1-dicarboxylate

dimethyl-3-(1-acetoxyethylidene)-4-ethylidenecyclopentane-1,1-dicarboxylate

Conditions
ConditionsYield
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

INDANE

A

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

1H-indene-1,3(2H)-dione

B

inden-1-one
83-33-0

inden-1-one

Conditions
ConditionsYield
With dipyridinium dichromate; adogen 464; dihydrogen peroxide; sodium carbonate In various solvent(s) for 24h; Oxidation; Heating;A 18%
B 38%
C18H17NO2

C18H17NO2

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere;35%
2-propylindan-1,3-dione
14570-43-5

2-propylindan-1,3-dione

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
In acetonitrile for 4h; UV-irradiation;28%
INDANE
496-11-7

INDANE

A

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

1H-indene-1,3(2H)-dione

B

3-hydroxy-2,3-dihydro-1H-inden-1-one
26976-59-0

3-hydroxy-2,3-dihydro-1H-inden-1-one

C

inden-1-one
83-33-0

inden-1-one

Conditions
ConditionsYield
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

2-formylindane-1,3-dione

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
With hydrogenchloride
2-bromo-indan-1,3-dione
7319-63-3

2-bromo-indan-1,3-dione

A

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

1H-indene-1,3(2H)-dione

B

2,2-dibromo-indan-1,3-dione
1685-97-8

2,2-dibromo-indan-1,3-dione

Conditions
ConditionsYield
With water
[2,2']biindenyl-1,3,1',3'-tetraone
6940-95-0

[2,2']biindenyl-1,3,1',3'-tetraone

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
With dihydrogen peroxide Uebersaettigen der Loesung mit Schwefelsaeure;
2,2-bis-(1,3-dioxo-indan-2-yl)-acenaphthen-1-one
103165-42-0

2,2-bis-(1,3-dioxo-indan-2-yl)-acenaphthen-1-one

A

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

1H-indene-1,3(2H)-dione

B

2-(2-oxo-acenaphthen-1-ylidene)-indan-1,3-dione
850645-51-1

2-(2-oxo-acenaphthen-1-ylidene)-indan-1,3-dione

Conditions
ConditionsYield
With sulfuric acid
3-methoxy-1-oxo-indene-2-carboxylic acid ethyl ester
87768-18-1

3-methoxy-1-oxo-indene-2-carboxylic acid ethyl ester

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
at 100℃;
2-bromo-1,3-dioxo-indan-2-carboxylic acid ethyl ester
74307-85-0

2-bromo-1,3-dioxo-indan-2-carboxylic acid ethyl ester

A

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

1H-indene-1,3(2H)-dione

B

2,2-dibromo-indan-1,3-dione
1685-97-8

2,2-dibromo-indan-1,3-dione

Conditions
ConditionsYield
With water
ethyl 3-amino-1-oxo-1H-indene-2-carboxylate

ethyl 3-amino-1-oxo-1H-indene-2-carboxylate

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

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

1H-indene-1,3(2H)-dione

1-(1,3-dioxo-indan-2-yl)-4-(1,3-dioxo-indan-2-ylidene)-3,4-dihydro-2H-pyrrolium betaine
15365-99-8

1-(1,3-dioxo-indan-2-yl)-4-(1,3-dioxo-indan-2-ylidene)-3,4-dihydro-2H-pyrrolium betaine

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
at 210 - 220℃; under 0.1 Torr;
2‑(2‑hydroxybenzylidene)‑1H‑indene‑1,3(2H)‑dione
25299-18-7

2‑(2‑hydroxybenzylidene)‑1H‑indene‑1,3(2H)‑dione

phenylhydrazine
100-63-0

phenylhydrazine

A

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

1H-indene-1,3(2H)-dione

B

salicylaldehyde
90-02-8

salicylaldehyde

vinyl acetate
108-05-4

vinyl acetate

Phthaloyl dichloride
88-95-9

Phthaloyl dichloride

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
With aluminium trichloride
3-methylidenephthalide
3453-63-2

3-methylidenephthalide

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

2-diazo-3-hydroxy-1-indanone

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
tin(ll) chloride In dichloromethane Ambient temperature;
1,3-indandione anion
19968-95-7

1,3-indandione anion

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

1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

2-bromo-indan-1,3-dione
7319-63-3

2-bromo-indan-1,3-dione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

2-aminoacetophenone
551-93-9

2-aminoacetophenone

10-methyl-11H-indeno[1,2-b]quinolin-11-one
142790-83-8

10-methyl-11H-indeno[1,2-b]quinolin-11-one

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

3,5-di-t-butyl-4-hydroxybenzaldehyde
1620-98-0

3,5-di-t-butyl-4-hydroxybenzaldehyde

(Z)-2-(3,5-di-tert-butyl-4-hydroxybenzylidene)-1H-indene-1,3(2H)-dione
53566-09-9

(Z)-2-(3,5-di-tert-butyl-4-hydroxybenzylidene)-1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

(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

(Z)-5a,6,7,9a-Tetrahydro-5a,6-tetramethylene-11-[ethoxycarbonyl(nitro)methylene]naphtho[1',2':4,5]imidazo[1,2-a]pyridine

C40H30N2O2

C40H30N2O2

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; methylene exchange;100%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

2-(4-chlorophenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

2-(4-chlorophenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

1-naphthaldehyde
66-77-3

1-naphthaldehyde

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

2-(naphthalen-1-yl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

2-(naphthalen-1-yl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

2-(4-hydroxyphenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

2-(4-hydroxyphenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

2-(4-cyanophenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

2-(4-cyanophenyl)-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

methyl 4-formylbenzoate
1571-08-0

methyl 4-formylbenzoate

2-[4-(methoxycarbonyl)phenyl]-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

2-[4-(methoxycarbonyl)phenyl]-6-phenylspiro[cyclohexane-1,2'-indan]-1',3',4-trione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

3′-(3-nitrophenyl)dispiro[indene-2,1′-cyclopropane-2′,2′′-indene]-1,1′′,3,3′′-tetraone
18691-32-2

3′-(3-nitrophenyl)dispiro[indene-2,1′-cyclopropane-2′,2′′-indene]-1,1′′,3,3′′-tetraone

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

3'-(4-nitrophenyl)-dispiro[indan-2,1'-cyclopropane-2',2''-indan]-1,1'',3,3''-tetrone
18691-31-1

3'-(4-nitrophenyl)-dispiro[indan-2,1'-cyclopropane-2',2''-indan]-1,1'',3,3''-tetrone

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

2,4-dichlorobenzaldeyhde
874-42-0

2,4-dichlorobenzaldeyhde

3′-(2,4-dichlorophenyl)dispiro[indene-2,1′-cyclopropane-2′,2′′-indene]-1,1′′,3,3′′-tetraone
7090-75-7

3′-(2,4-dichlorophenyl)dispiro[indene-2,1′-cyclopropane-2′,2′′-indene]-1,1′′,3,3′′-tetraone

Conditions
ConditionsYield
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

formaldehyd

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

1H-indene-1,3(2H)-dione

dispiro[indene-2,1'-cyclopropane-2',2''-indene]-1,1'',3,3''-tetraone
106144-67-6

dispiro[indene-2,1'-cyclopropane-2',2''-indene]-1,1'',3,3''-tetraone

Conditions
ConditionsYield
With bromocyane; sodium ethanolate In methanol at 0 - 20℃; for 0.00416667h; Sealed tube;100%
4-hydroxy-3-ethoxybenzaldehyde
121-32-4

4-hydroxy-3-ethoxybenzaldehyde

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

1H-indene-1,3(2H)-dione

2-(3-ethoxy-4-hydroxybenzylidene)-1H-indene-1,3(2H)-dione

2-(3-ethoxy-4-hydroxybenzylidene)-1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In water at 20℃; Inert atmosphere;99.8%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

2-(p-nitrobenzylidene)indan-1,3-dione
15875-60-2

2-(p-nitrobenzylidene)indan-1,3-dione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

2,5-dimethoxybenzaldehyde
93-02-7

2,5-dimethoxybenzaldehyde

2-(2,5-dimethoxybenzylidene)-1H-indene-1,3(2H)-dione
67200-96-8

2-(2,5-dimethoxybenzylidene)-1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

2,4-Dihydroxybenzaldehyde
95-01-2

2,4-Dihydroxybenzaldehyde

2-(2,4-dihydroxybenzylidene)-1H-indene-1,3(2H)-dione
78426-08-1

2-(2,4-dihydroxybenzylidene)-1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

propargyl bromide
106-96-7

propargyl bromide

2,2-di(prop-2-yn-1-yl)-1H-indene-1,3(2H)-dione
24241-98-3

2,2-di(prop-2-yn-1-yl)-1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

C22H22O5

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

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
ConditionsYield
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

1H-indene-1,3(2H)-dione

allyl alcohol
107-18-6

allyl alcohol

2,2-diallyl-1H-indene-1,3(2H)-dione
81055-89-2

2,2-diallyl-1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

benzaldehyde
100-52-7

benzaldehyde

2-benzyl-indan-1,3-dione
890-44-8

2-benzyl-indan-1,3-dione

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

benzene
71-43-2

benzene

3,3-diphenyl-indan-1-one
55010-17-8

3,3-diphenyl-indan-1-one

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 20℃; for 24h;99%
3-(4-bromophenylamino)-5,5-dimethylcyclohex-2-enone
106518-84-7

3-(4-bromophenylamino)-5,5-dimethylcyclohex-2-enone

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

1H-indene-1,3(2H)-dione

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

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

10-(4-bromophenyl)-5-(2-chlorophenyl)-7,8-dihydro-7,7-dimethyl-5H-indeno[1,2-b]quinolin-9,11(6H,10H)-dione

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 90℃; for 8h;99%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one
18940-21-1

5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

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

7,8-dihydro-7,7-dimethyl-5-(2-nitrophenyl)-10-phenyl-5H-indeno[1,2-b]quinolin-9,11(6H,10H)-dione

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 90℃; for 6h;99%
(5-methyl-pyridin-2-yl)amine
1603-41-4

(5-methyl-pyridin-2-yl)amine

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

1H-indene-1,3(2H)-dione

pyrimidine-2,4,5,6(1H,3H)-tetraone
61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9

pyrimidine-2,4,5,6(1H,3H)-tetraone

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

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

Conditions
ConditionsYield
In chloroform for 1h; Reflux;99%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

thieno[3,2-b]thiophene-2-carbaldehyde
31486-86-9

thieno[3,2-b]thiophene-2-carbaldehyde

C16H8O2S2

C16H8O2S2

Conditions
ConditionsYield
With aluminum oxide In dichloromethane at 25℃; for 12h; Knoevenagel Condensation;99%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

2-Formylthieno<2,3-b>thiophene
31486-85-8

2-Formylthieno<2,3-b>thiophene

C16H8O2S2

C16H8O2S2

Conditions
ConditionsYield
With aluminum oxide In dichloromethane at 25℃; for 12h; Knoevenagel Condensation;99%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

1-benzyl-4-(pyrrolidin-1-yl)indoline-2,3-dione

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

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
ConditionsYield
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

1H-indene-1,3(2H)-dione

1-(2-chlorobenzyl)-4-(pyrrolidin-1-yl)indoline-2,3-dione

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

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
ConditionsYield
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

1H-indene-1,3(2H)-dione

1-(4-bromophenyl)-4-(4-chlorophenyl)but-3-yne-1,2-dione

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

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

1,3-Indanedione Chemical Properties

The molecular formula of 1,3-Indanedione(606-23-5) is C9H6O2  and its formula weight is  146.14.
The density of  1,3-Indanedione(606-23-5) is 1.37 g/cm3  and it has a  melting point of  129-132 °C(lit.). The boiling point is  283°C.
The chemical synonyms of 1,3-Indanedione(606-23-5) are 1,3-DIOXOINDANE;1,3-DIKETOHYDRINDENE;1,3-HYDRINDENEDIONE;1,3-Indanedione;1,3-INDANEDIONE;AURORA KA-7365;DIKETOHYDRINDENE;1,3-Indanone
The molecular structure of 1,3-Indanedione(606-23-5):

1,3-Indanedione Uses

1,3-Indanedione(606-23-5) is an anticoagulant used as a rodenticide.
Certain derivatives are used in human medicine.

1,3-Indanedione Toxicity Data With Reference

RTECS#: CAS# 606-23-5: NK5070000 
LD50/LC50: ipr-mus LDLo:100 mg/kg ARTODN    Archives of Toxicology. 33 (1975),191.
Carcinogenicity: 1,3-INDANEDIONE, 97% - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. 
Other: See actual entry in RTECS for complete information.

1,3-Indanedione Consensus Reports

Reported in EPA TSCA Inventory.

1,3-Indanedione Safety Profile

A poison by intraperitoneal route. Experimental teratogenic and reproductive effects. When heated to decomposition it emits acrid smoke and fumes.
Hazard Codes  Xi
Risk Statements  33-36/37/38
Safety Statements  24/25-36/37/39-27-26
WGK Germany  3
RTECS  NK5070000
HS Code  29143900

1,3-Indanedione Specification

Chemical Stability: Stable under normal temperatures and pressures. 
Conditions to Avoid: Incompatible materials. 
Incompatibilities with Other Materials Strong oxidizing agents. 
Hazardous Decomposition Products Irritating and toxic fumes and gases. 
Hazardous Polymerization Has not been reported.
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