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615-13-4

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615-13-4 Usage

Uses

Different sources of media describe the Uses of 615-13-4 differently. You can refer to the following data:
1. 2-Indanone is an indanone with an oxo substituent at position 2. It is a metabolite of indane. It has a role as a xenobiotic metabolite. 2-Indanone is an intermediate for the preparation of aprindine hydrochloride and ceforanide. It is an important intermediate in organic synthesis.
2. 2-Indanone undergoes TiCl4-Mg mediated coupling with CHBr3 to yield dibromomethyl carbinol. It reacts with 5,5-dimethyl-3-pyrazolidinone to yield 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone. On photolysis by 266-nm one-photon excitation yields o-xylylene. It was used as starting reagent in the synthesis of indene-fused porphyrins.

Preparation

2-Indanone is prepared by using acetic acid as solvent, acetic anhydride as catalyst and through hydrogen peroxide oxidation into 1, 2-indenediol, which reacted with dilute sulfuric acid solution in order to obtain crude 2-indanone. Finally, vacuum sublimation to obtain 2-indanone with high-purity, the total yield is 89%.

Chemical Properties

Wet crystalline aggregates

Definition

ChEBI: An indanone with an oxo substituent at position 2. It is a metabolite of indane.

Synthesis Reference(s)

Chemistry Letters, 11, p. 325, 1982Organic Syntheses, Coll. Vol. 5, p. 647, 1973Tetrahedron Letters, 15, p. 3789, 1974 DOI: 10.1016/S0040-4039(01)92010-6

General Description

2-Indanone undergoes TiCl4-Mg mediated coupling with CHBr3 to yield dibromomethyl carbinol. It reacts with 5,5-dimethyl-3-pyrazolidinone to yield 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone. 2-Indanone on photolysis by 266-nm one-photon excitation yields o-xylylene.

Check Digit Verification of cas no

The CAS Registry Mumber 615-13-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 5 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 615-13:
(5*6)+(4*1)+(3*5)+(2*1)+(1*3)=54
54 % 10 = 4
So 615-13-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O/c10-9-5-7-3-1-2-4-8(7)6-9/h1-4H,5-6H2

615-13-4 Well-known Company Product Price

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  • Alfa Aesar

  • (A12574)  2-Indanone, 98%   

  • 615-13-4

  • 5g

  • 482.0CNY

  • Detail
  • Alfa Aesar

  • (A12574)  2-Indanone, 98%   

  • 615-13-4

  • 25g

  • 2103.0CNY

  • Detail
  • Alfa Aesar

  • (A12574)  2-Indanone, 98%   

  • 615-13-4

  • 100g

  • 7340.0CNY

  • Detail

615-13-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name indan-2-one

1.2 Other means of identification

Product number -
Other names 1,3-dihydroinden-2-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:615-13-4 SDS

615-13-4Synthetic route

Formic acid 1H-inden-2-yl ester
113388-65-1

Formic acid 1H-inden-2-yl ester

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water for 7h; Ambient temperature;98%
1-indene
95-13-6

1-indene

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With oxygen; cobalt(II) acetate; isobutyraldehyde In acetonitrile at 60℃; for 1h;97%
Stage #1: 1-indene With dihydrogen peroxide; acetic anhydride; acetic acid at 40 - 55℃; for 14h; Green chemistry;
Stage #2: With sulfuric acid In water at 5 - 50℃; for 3h; Green chemistry;
97.1%
With chloropyridinecobaloxime(III); water; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 24h; Wacker Oxidation; Inert atmosphere; Schlenk technique; Irradiation; regioselective reaction;80%
2,3-epoxyindene
768-22-9

2,3-epoxyindene

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With Dowex-50W In water for 0.5h; Heating;95%
With pentacarbonyliron In benzene for 3h; Irradiation;85%
With indium(III) chloride In tetrahydrofuran at 25℃; for 0.75h; Rearrangement;85%
Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 0.25h; Heating;95%
With sulfuric acid
Multi-step reaction with 2 steps
1: thionyl chloride; pyridine / benzene / 3 h
2: acetonitrile / 2 h / Irradiation; Inert atmosphere
View Scheme
C8H8*C3FeO3

C8H8*C3FeO3

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In acetone for 3.66667h; reag. added in three portions;90%
(orthoquinodimethane)tricarbonyliron
12181-95-2

(orthoquinodimethane)tricarbonyliron

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In acetone anh. (NH4)2Ce(NO3)6 was added portionwise to a stirred soln. of (C8H8)Fe(CO)3 in anh. acetone (after 50 min and 70 min), after 100 min of reaction addn. of H2O, mixture was extracted with CH2Cl2 (4 times), extract was dried (MgSO4), solvent evaporation;; filtration through a short column of silica gel; white crystals with m.p. 54-55°C were obtained;;90%
1-(trimethylsilyl)-3-phenylprop-1-yne
31683-47-3

1-(trimethylsilyl)-3-phenylprop-1-yne

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With 8-isopropyl-quinoline-N-oxide; [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(NTf2)] In fluorobenzene at 60℃;90%
triethyl(3-phenylprop-1-yn-1-yl)silane

triethyl(3-phenylprop-1-yn-1-yl)silane

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With 8-isopropyl-quinoline-N-oxide; [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(NTf2)] In fluorobenzene at 60℃;90%
dimethyl(phenyl)(3-phenylprop-1-yn-1-yl)silane
79275-63-1

dimethyl(phenyl)(3-phenylprop-1-yn-1-yl)silane

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With 8-isopropyl-quinoline-N-oxide; [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(NTf2)] In fluorobenzene at 60℃;90%
1-indene
95-13-6

1-indene

A

2-(o-tolyl)-2-oxo-ethanale
63440-60-8

2-(o-tolyl)-2-oxo-ethanale

B

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With nitrobenzene In acetonitrile for 24h;A 85%
B 9%
With p-nitrobenzene iodide In acetonitrile for 18h;A 40%
B 50%
malononitrile
109-77-3

malononitrile

A

2-indanone
615-13-4

2-indanone

B

(3aS,8aR)-(8,8a-Dihydro-3aH-indeno[1,2-d]oxazol-2-yl)-acetonitrile

(3aS,8aR)-(8,8a-Dihydro-3aH-indeno[1,2-d]oxazol-2-yl)-acetonitrile

C

[3aS-[2(3'aR*,8'aS*),3a,8a]]methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole]
175166-49-1

[3aS-[2(3'aR*,8'aS*),3a,8a]]methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole]

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane -40 deg C to room t.; Yields of byproduct given;A n/a
B 80%
C n/a
With trifluorormethanesulfonic acid In dichloromethane Product distribution; -40 deg C to room t.; reactions with var. dinitriles;A n/a
B 10%
C 60%
With trifluorormethanesulfonic acid In dichloromethane -40 deg C to room t.;A n/a
B 10%
C 60%
indan-2-ol
4254-29-9

indan-2-ol

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With dimethyl sulfoxide; triethylamine In dichloromethane at -40 - 20℃; for 8h;79%
With [Cu6(pyridine-2-thiolate)6]; potassium hydroxide In toluene at 70℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere;78%
With [Cu6(SC5H4N)6]; potassium hydroxide In toluene at 70℃; for 24h; Glovebox; Inert atmosphere;78%
propargyl benzene
10147-11-2

propargyl benzene

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With 2-(tert-butyl)-6-chloropyridine 1-oxide; C45H57AuF6NO9PS2 In chloroform at 60℃; for 2h; Reagent/catalyst; Temperature; Time;77%
With 3,5-dicholoropyridine N-oxide; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In dichloromethane at 20℃; for 8h; Reagent/catalyst;43%
indan-2-one oxime
3349-63-1

indan-2-one oxime

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With bismuth(III) nitrate; Montmorillonite K 10; copper diacetate In water; acetone for 3h; Heating;76%
With bismuth(lll) trifluoromethanesulfonate; bismuth(III) bromide In water; acetone; acetonitrile for 0.7h; Heating;
With gold(III) tribromide; dimethylglyoxal In ethanol; water at 20℃; for 15h; pH=7;100 %Spectr.
tert-butyldimethyl(3-phenylprop-1-yn-1-yl)silane

tert-butyldimethyl(3-phenylprop-1-yn-1-yl)silane

A

1-(tert-butyldimethylsilyl)-1H-inden-2(3H)-one

1-(tert-butyldimethylsilyl)-1H-inden-2(3H)-one

B

2-(tert-butyldimethylsilyl)-3-phenylpropanoic acid

2-(tert-butyldimethylsilyl)-3-phenylpropanoic acid

C

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With 8-isopropyl-quinoline-N-oxide; [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(NTf2)] In fluorobenzene at 60℃; Reagent/catalyst;A 20%
B 75%
C 5%
1-(triisopropylsilyl)-1H-inden-2(3H)-one

1-(triisopropylsilyl)-1H-inden-2(3H)-one

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.166667h; Inert atmosphere;68%
With tetrabutyl ammonium fluoride In tetrahydrofuran68%
2-nitrothiophene
609-40-5

2-nitrothiophene

1-indene
95-13-6

1-indene

A

2-nitro-indene
16021-01-5

2-nitro-indene

B

2-(o-tolyl)-2-oxo-ethanale
63440-60-8

2-(o-tolyl)-2-oxo-ethanale

C

2-indanone
615-13-4

2-indanone

D

2-(2-thienyl)indene
150994-10-8

2-(2-thienyl)indene

Conditions
ConditionsYield
In acetonitrile for 1h;A 20%
B 6%
C 8%
D 66%
1-diazo-3-phenyl-2-propanone
4250-02-6

1-diazo-3-phenyl-2-propanone

A

cyclohepta-2,4,6-trienylbenzylketone
98405-65-3

cyclohepta-2,4,6-trienylbenzylketone

B

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With rhodium(II) trifluoroacetate dimer In benzene at 22℃;A 64%
B 18%
1-diazo-3-phenyl-2-propanone
4250-02-6

1-diazo-3-phenyl-2-propanone

benzene
71-43-2

benzene

A

cyclohepta-2,4,6-trienylbenzylketone
98405-65-3

cyclohepta-2,4,6-trienylbenzylketone

B

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With rhodium(II) trifluoroacetate dimer at 22℃;A 64%
B 18%
Indan-2-spiro-3'-(1',2',4'-trioxane)-6'-spiro-1''-cyclohexane
98809-66-6

Indan-2-spiro-3'-(1',2',4'-trioxane)-6'-spiro-1''-cyclohexane

A

cyclohexanone
108-94-1

cyclohexanone

B

2-indanone
615-13-4

2-indanone

C

C16H20O3

C16H20O3

Conditions
ConditionsYield
In decane at 190℃; for 8h;A n/a
B n/a
C 53%
1-diazo-3-phenyl-2-propanone
4250-02-6

1-diazo-3-phenyl-2-propanone

benzene
71-43-2

benzene

A

2-indanone
615-13-4

2-indanone

B

1,3-Diphenylpropanone
102-04-5

1,3-Diphenylpropanone

Conditions
ConditionsYield
rhodium(II) trifluoroacetate dimer for 1h; Ambient temperature;A 49%
B 31%
carbon monoxide
201230-82-2

carbon monoxide

α,α'-dibromo-o-xylene
91-13-4

α,α'-dibromo-o-xylene

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With sodium tetracarbonyl cobaltate In tetrahydrofuran for 8h; Heating;46%
1-diazo-3-phenyl-2-propanone
4250-02-6

1-diazo-3-phenyl-2-propanone

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With dirhodium tetraacetate In dichloromethane42%
dirhodium tetraacetate In dichloromethane for 24h;42%
[2-((4aR,9aS)-1-Methyl-1,2,3,4a,9,9a-hexahydro-indeno[1,2-b]pyrazin-4-yl)-pyridin-3-yl]-methanol

[2-((4aR,9aS)-1-Methyl-1,2,3,4a,9,9a-hexahydro-indeno[1,2-b]pyrazin-4-yl)-pyridin-3-yl]-methanol

cis-4a,5,6,7,12,12c-hexahydro-5-methyl-4H-5,7a,8-triazabenzo<5,6>cyclohepta<1,2,3,4-def>fluorene

cis-4a,5,6,7,12,12c-hexahydro-5-methyl-4H-5,7a,8-triazabenzo<5,6>cyclohepta<1,2,3,4-def>fluorene

B

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With PPA at 100℃; for 3h;A 39%
B 13%
2,2-dimethylmalononitrile
7321-55-3

2,2-dimethylmalononitrile

A

2-indanone
615-13-4

2-indanone

B

2-{(3aS,8aR)-8,8a-dihydro-3aH-indeno[1,2-d][1,3]-oxazol-2-yl}-2-methylpropanenitrile

2-{(3aS,8aR)-8,8a-dihydro-3aH-indeno[1,2-d][1,3]-oxazol-2-yl}-2-methylpropanenitrile

C

(3aS,3a'S,8aR,8a'R)-2,2'-(propane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)

(3aS,3a'S,8aR,8a'R)-2,2'-(propane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane -40 deg C to room t.; Yield given;A n/a
B n/a
C 30%
With trifluorormethanesulfonic acid In dichloromethane -40 deg C to room t.; Yields of byproduct given;A n/a
B n/a
C 30%
1-indene
95-13-6

1-indene

B

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With potassium phosphate; Leifsonia sp. S749 alcohol dehydrogenase; Rhodococcus sp. ST-10 styrene monooxygenase; NAD+; oxygen; isopropyl alcohol; flavin adenine dinucleotide at 25℃; for 24h; pH=7.5; Microbiological reaction; enantioselective reaction;A 21%
B 27%
1-indene
95-13-6

1-indene

A

indan-1,2-diol
4370-02-9

indan-1,2-diol

B

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With oxygen In acetonitrile at 25℃; for 24h; Sealed tube; Irradiation; Green chemistry;A 26%
B 10%
2,3-dihydro-1H-indene 2,3-oxide
768-22-9, 67528-26-1, 71214-81-8, 85354-35-4

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

(+/-)-N-(cis-2-hydroxy-indan-1-yl)-acetamide
115146-09-3

(+/-)-N-(cis-2-hydroxy-indan-1-yl)-acetamide

(+/-)-N-(trans-2-hydroxy-indan-1-yl)-acetamide
115146-09-3

(+/-)-N-(trans-2-hydroxy-indan-1-yl)-acetamide

C

2-indanone
615-13-4

2-indanone

D

Sulfuric acid mono-(2-hydroxy-indan-1-yl) ester

Sulfuric acid mono-(2-hydroxy-indan-1-yl) ester

Conditions
ConditionsYield
With sulfuric acid; acetonitrile at -40℃; Further byproducts given;A n/a
B n/a
C 12%
D n/a
2,3-dihydro-1H-indene 2,3-oxide
768-22-9, 67528-26-1, 71214-81-8, 85354-35-4

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

acetonitrile
75-05-8

acetonitrile

(+/-)-N-(cis-2-hydroxy-indan-1-yl)-acetamide
115146-09-3

(+/-)-N-(cis-2-hydroxy-indan-1-yl)-acetamide

(+/-)-N-(trans-2-hydroxy-indan-1-yl)-acetamide
115146-09-3

(+/-)-N-(trans-2-hydroxy-indan-1-yl)-acetamide

C

2-indanone
615-13-4

2-indanone

D

Sulfuric acid mono-(2-hydroxy-indan-1-yl) ester

Sulfuric acid mono-(2-hydroxy-indan-1-yl) ester

(3aS,8aR)-2-Methyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazole; compound with sulfuric acid

(3aS,8aR)-2-Methyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazole; compound with sulfuric acid

Conditions
ConditionsYield
With sulfuric acid at -40℃; Mechanism;A n/a
B n/a
C 12%
D n/a
E n/a
1-indene
95-13-6

1-indene

A

2,3-epoxyindene
768-22-9

2,3-epoxyindene

B

2-indanone
615-13-4

2-indanone

Conditions
ConditionsYield
With N-(benzenesulfonyl)-3-phenyloxaziridine In chloroform at 60℃; for 3h;A 40 % Chromat.
B 10%
Stage #1: 1-indene With manganese(II) acetate; 1-bicyclo[2.2.1]hept-5-en-2-yl-CH2-4,7-diMe[1,4,7]triazonane In methanol; acetone at 0℃; for 0.25h;
Stage #2: With oxalic buffer; dihydrogen peroxide In methanol; acetone at 0 - 2℃; for 4.5h; Further stages.;
With 3H-2,1-benzoxaselenole Se-oxide; dihydrogen peroxide; magnesium sulfate; trifluoroacetic acid In dichloromethane at 20℃; for 13h;
With Ti0.85V0.15O2; dihydrogen peroxide In methanol at 20℃; for 2h;
2-indanone
615-13-4

2-indanone

indan-2-ol
4254-29-9

indan-2-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 0℃; Inert atmosphere;100%
With methanol; sodium tetrahydroborate at 25℃; for 1h;98%
With tetrakis[3,5-bis(trifluoromethyl)phenyl]boric acid bis(diethyl ether) complex; C32H63CoNP2Si; hydrogen In tetrahydrofuran at 60℃; under 760.051 Torr; for 48h;97%
pyrrolidine
123-75-1

pyrrolidine

2-indanone
615-13-4

2-indanone

1-(1H-inden-2-yl)pyrrolidine
39157-79-4

1-(1H-inden-2-yl)pyrrolidine

Conditions
ConditionsYield
In benzene for 3h; Condensation; Heating;100%
With toluene-4-sulfonic acid In benzene for 4h; Heating;79%
In toluene at 70℃; for 24h; Molecular sieve 4Å;48%
1-chloroethyl p-tolyl sulfoxide
50635-71-7, 50635-72-8, 31350-93-3

1-chloroethyl p-tolyl sulfoxide

2-indanone
615-13-4

2-indanone

2-<1-chloro-1-(p-tolylsulfinyl)ethyl>-2-indanol
134970-40-4

2-<1-chloro-1-(p-tolylsulfinyl)ethyl>-2-indanol

Conditions
ConditionsYield
at -70℃;100%
With n-butyllithium; diisopropylamine In tetrahydrofuran at -65℃; for 0.416667h;93%
With lithium diisopropyl amide 1.) THF; Multistep reaction;
With lithium diisopropyl amide 1) THF, -60 deg C, 10 min; Yield given. Multistep reaction;
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

2-indanone
615-13-4

2-indanone

1-[(dimethylamino)methylene]-1,3-dihydro-2H-inden-2-one

1-[(dimethylamino)methylene]-1,3-dihydro-2H-inden-2-one

Conditions
ConditionsYield
In tetrahydrofuran100%
In chloroform Ambient temperature;72%
2-indanone
615-13-4

2-indanone

(S)-3-Amino-2-oxo-1-piperidineacetic acid, benzyl ester hydrochloride

(S)-3-Amino-2-oxo-1-piperidineacetic acid, benzyl ester hydrochloride

[(S)-3-(Indan-2-ylamino)-2-oxo-piperidin-1-yl]-acetic acid benzyl ester
220624-65-7

[(S)-3-(Indan-2-ylamino)-2-oxo-piperidin-1-yl]-acetic acid benzyl ester

Conditions
ConditionsYield
With DCE; sodium tris(acetoxy)borohydride; triethylamine Ambient temperature;100%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2-indanone
615-13-4

2-indanone

2-[(trimethylsilyl)oxy]-2,3-dihydro-1H-indene-2-carbonitrile
55589-22-5

2-[(trimethylsilyl)oxy]-2,3-dihydro-1H-indene-2-carbonitrile

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃;100%
potassium-exchanged zirconium hydrogen phosphate In dichloromethane for 1h; Heating;86%
With 18-crown-6 ether; zinc(II) iodide
2-indanone
615-13-4

2-indanone

cinnamyl chloride
2687-12-9

cinnamyl chloride

2-(1-phenyl-allyl)-indan-2-ol
851934-06-0

2-(1-phenyl-allyl)-indan-2-ol

Conditions
ConditionsYield
With ammonium chloride; zinc In tetrahydrofuran for 19h; Barbier-type allylation reaction;100%
N-(tert-butyl)-N-(1-chloro-1,1-dimethylsilyl)amine
60556-33-4

N-(tert-butyl)-N-(1-chloro-1,1-dimethylsilyl)amine

2-indanone
615-13-4

2-indanone

N-(tert-butyl)-N-(1-(1H-2-indenyloxy)-1,1-dimethylsilyl)amine
308847-01-0

N-(tert-butyl)-N-(1-(1H-2-indenyloxy)-1,1-dimethylsilyl)amine

Conditions
ConditionsYield
With diisopropylamine In tetrahydrofuran99.7%
6-hydroxy-[1,3]dioxolo[4,5-e]isobenzofuran-8(6H)-on
77632-09-8

6-hydroxy-[1,3]dioxolo[4,5-e]isobenzofuran-8(6H)-on

2-indanone
615-13-4

2-indanone

6-(2-oxo-2,3-dihydro-1H-inden-1-yl)-[1,3]dioxolo[4,5-e]isobenzofuran-8(6H)-one
78673-86-6, 78673-87-7

6-(2-oxo-2,3-dihydro-1H-inden-1-yl)-[1,3]dioxolo[4,5-e]isobenzofuran-8(6H)-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 5h; Heating;99%
carbon dioxide
124-38-9

carbon dioxide

2-indanone
615-13-4

2-indanone

methyl iodide
74-88-4

methyl iodide

methyl 2-oxo-2,3-dihydro-1H-indane-1-carboxylate
104620-34-0

methyl 2-oxo-2,3-dihydro-1H-indane-1-carboxylate

Conditions
ConditionsYield
With poly(dimethylsiloxane-co-methylhydrosiloxane)trimethylsilyl terminated supported 1-carboxy-6-ethyl-1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 25 - 27℃; under 760.051 Torr; for 4h;99%
2-(1H-pyrrol-1-yl)aniline
6025-60-1

2-(1H-pyrrol-1-yl)aniline

2-indanone
615-13-4

2-indanone

1,3-dihydro-5'H-spiro[indene-2,4'-pyrrolo[1,2-a]quinoxaline]

1,3-dihydro-5'H-spiro[indene-2,4'-pyrrolo[1,2-a]quinoxaline]

Conditions
ConditionsYield
With trifluoroacetic anhydride In tetrahydrofuran at 100℃; Sealed tube; Inert atmosphere;99%
2-indanone
615-13-4

2-indanone

Sodium; 2-hydroxy-indan-2-sulfonate
67851-69-8

Sodium; 2-hydroxy-indan-2-sulfonate

Conditions
ConditionsYield
With sodium hydrogensulfite In water98%
With benzyl butanoate; sodium hydrogensulfite In methanol; water for 0.00833333h; chemoselective reaction;
5-methoxylindole
1006-94-6

5-methoxylindole

2-indanone
615-13-4

2-indanone

3-(1H-inden-2-yl)-5-methoxy-1H-indole

3-(1H-inden-2-yl)-5-methoxy-1H-indole

Conditions
ConditionsYield
With L-Tartaric acid; 1,1-Dimethylurea at 70℃; for 3h;98%
2-indanone
615-13-4

2-indanone

2,3-dihydro-1H-inden-2-amine
2975-41-9

2,3-dihydro-1H-inden-2-amine

Conditions
ConditionsYield
With ammonium formate; C25H31ClIrN2OP at 50℃; for 18h; Leukardt-Wallach Amination; Sealed tube;98%
With palladium on activated charcoal; hydrogen; acetic acid; benzylamine In isopropyl alcohol at 80℃; under 22502.3 Torr; Solvent; Pressure; Autoclave;93%
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 °C / Schlenk technique; Reflux; Inert atmosphere
2: triethylamine / dichloromethane / 0 - 20 °C / Schlenk technique; Inert atmosphere
3: sodium azide / N,N-dimethyl-formamide / 90 °C / Schlenk technique; Inert atmosphere
4: hydrogen; palladium on carbon / ethyl acetate / 12 h / 750.08 Torr / Schlenk technique
View Scheme
thiosemicarbazide
79-19-6

thiosemicarbazide

2-indanone
615-13-4

2-indanone

2-indanone thiosemicarbazone
60798-85-8

2-indanone thiosemicarbazone

Conditions
ConditionsYield
With acetic acid for 0.333333h;97.6%
With acetic acid In ethanol for 24h;
2-methoxyacetonitrile
1738-36-9

2-methoxyacetonitrile

2-indanone
615-13-4

2-indanone

(Z)-1-(1'-amino-2'-methoxy)ethylidene-2-indanone
1179322-07-6

(Z)-1-(1'-amino-2'-methoxy)ethylidene-2-indanone

Conditions
ConditionsYield
With heptahydridobis(triphenylphosphine)rhenium In tetrahydrofuran at 150℃; for 5h; Inert atmosphere; teflon-cocked sealed tube;97%
anthranilic acid amide
28144-70-9

anthranilic acid amide

2-indanone
615-13-4

2-indanone

1,3-dihydro-1'H-spiro[indene-2,2'-quinazolin]-4'(3'H)-one
878733-86-9

1,3-dihydro-1'H-spiro[indene-2,2'-quinazolin]-4'(3'H)-one

Conditions
ConditionsYield
With Amberlyst-15 In acetonitrile at 20℃; for 0.0333333h; Irradiation; Green chemistry;97%
2-amino-5-iodoanthranilamide
32658-67-6

2-amino-5-iodoanthranilamide

2-indanone
615-13-4

2-indanone

6'-iodo-1,3-dihydro-1'H-spiro[indene-2,2'-quinazolin]-4'(3'H)-one
1420904-43-3

6'-iodo-1,3-dihydro-1'H-spiro[indene-2,2'-quinazolin]-4'(3'H)-one

Conditions
ConditionsYield
With Amberlyst-15 In acetonitrile at 20℃; for 0.0333333h; Irradiation; Green chemistry;97%
4-methoxyphenylhydrazine hydrochloride
19501-58-7

4-methoxyphenylhydrazine hydrochloride

2-indanone
615-13-4

2-indanone

5,6-dihydro-9-methoxyindeno<2,1-b>indole
139517-18-3

5,6-dihydro-9-methoxyindeno<2,1-b>indole

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; isopropyl alcohol96.7%
With hydrogenchloride In ethanol for 2h; Heating;50%
2-indanone
615-13-4

2-indanone

6-amino-3,4-benzodioxane
22013-33-8

6-amino-3,4-benzodioxane

N-2,3-Dihydro-benzo[1,4]dioxin-6-yl-N-indan-2-ylamine
1153745-37-9

N-2,3-Dihydro-benzo[1,4]dioxin-6-yl-N-indan-2-ylamine

Conditions
ConditionsYield
Stage #1: 2-indanone; 6-amino-3,4-benzodioxane With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 0 - 20℃;
Stage #2: With sodium hydroxide In ethyl acetate; 1,2-dichloro-ethane
96.5%
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 0 - 20℃;96.5%
2-furancarbonitrile
617-90-3

2-furancarbonitrile

2-indanone
615-13-4

2-indanone

C14H11NO2

C14H11NO2

Conditions
ConditionsYield
With heptahydridobis(triphenylphosphine)rhenium In tetrahydrofuran at 150℃; for 5h; Inert atmosphere; teflon-cocked sealed tube;96%
2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-indanone
615-13-4

2-indanone

2,3-Dihydro-1,3-benzothiazole<2-spiro-2'>indane
100067-31-0

2,3-Dihydro-1,3-benzothiazole<2-spiro-2'>indane

Conditions
ConditionsYield
In methanol for 0.333333h; Heating;95%
Nonafluorobutanesulfonyl fluoride
375-72-4

Nonafluorobutanesulfonyl fluoride

2-indanone
615-13-4

2-indanone

1H-inden-2-yl nonafluorobutanesulfonate
1003032-75-4

1H-inden-2-yl nonafluorobutanesulfonate

Conditions
ConditionsYield
With tert-butylimino-tri(pyrrolidino)phosphorane In tetrahydrofuran at 20℃; for 16h;95%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

2-indanone
615-13-4

2-indanone

C16H10Br2O

C16H10Br2O

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 20℃; for 3h;94%
toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

2-indanone
615-13-4

2-indanone

2-Indanon-p-tolylsulfonylhydrazon
87694-35-7

2-Indanon-p-tolylsulfonylhydrazon

Conditions
ConditionsYield
In ethanol for 3h; Heating;93%
tetraallyl tin
7393-43-3

tetraallyl tin

2-indanone
615-13-4

2-indanone

2,3-dihydro-2-(2-propenyl)inden-2-ol
389614-43-1

2,3-dihydro-2-(2-propenyl)inden-2-ol

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 12h;93%

615-13-4Relevant articles and documents

-

Johnson et al.

, p. 3793,3795,3796 (1974)

-

2-Indanone and Its Enol. The Effect of a Conjugated Phenyl Group on Enol and Enolate Stability

Keeffe, J.R.,Kresge, A.J.,Yin, Y.

, p. 8201 - 8206 (1988)

Rate and equilibrium constants for the interconversion of 2-indanone with its enol and enolate ion have been determined in dilute aqueous acid and base solution (ionic strength=0.10 M) at 25 deg C.These measurements provide the keto-enol equilibrium constant, pKE=3.84+-0.04; the acidity constant of the ketone ionizing as a carbon acid, pKaK=12.20+-0.08; and the acidity constant of the enol ionizing as an oxygen acid, pKaE=8.36+-0.09.Comparison of these results with values for acetone show that the effects of the benzene ring are large: a factor of 1E4.4 on KE, 1E7.0 on KaK, and 1E2.6 on KaE.Considerably smaller phenyl effects are estimated for the acyclic model ketone phenylacetone; reduced coplanarity in the latter is suggested as the major reason for the reduced effects.In terms of rate constants,the greater enol content of 2-indanone relative to acetone manifests itself in the acid-catalyzed reaction mainly as a largely reduced rate of enol ketonization and in the "uncatalyzed" reaction entirely by an increased rate of enolization.For hydroxide ion promoted enolate formation the phenyl effect appears roughly equally as an increase in the rate of enolate formation and a decrease in ketonization rate.It is suggested that the effects of a conjugated benzene ring on enol and enolate stability are fully expressed by the reactions of 2-indanone.

-

Askam,Deeks

, p. 2245 (1970)

-

g-C3N4/metal halide perovskite composites as photocatalysts for singlet oxygen generation processes for the preparation of various oxidized synthons

Corti, Marco,Chiara, Rossella,Romani, Lidia,Mannucci, Barbara,Malavasi, Lorenzo,Quadrelli, Paolo

, p. 2292 - 2298 (2021/04/12)

g-C3N4/metal halide perovskite composites were prepared and used for the first time as photocatalysts forin situ1O2generation to perform hetero Diels-Alder, ene and oxidation reactions with suitable dienes and alkenes. The standardized methodology was made applicable to a variety of olefinic substrates. The scope of the method is finely illustrated and the reactions afforded desymmetrized hydroxy-ketone derivatives, unsaturated ketones and epoxides. Some limitations were also observed, especially in the case of the alkene oxidations, and poor chemoselectivity was somewhere observed in this work which is the first application of MHP-based composites forin situ1O2generation. The experimental protocol can be used as a platform to further expand the knowledge and applicability of MHPs to organic reactions, since perovskites offer a rich variety of tuning strategies which may be explored to improve reaction yields and selectivities.

Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides

Ardiansah, Bayu,Kakiuchi, Kiyomi,Morimoto, Tsumoru,Tanimoto, Hiroki,Tomohiro, Takenori

, p. 8738 - 8741 (2021/09/08)

Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.

Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade

Franssen, Maurice C. R.,Hollmann, Frank,Martínez-Montero, Lía,Paul, Caroline E.,Süss, Philipp,Schallmey, Anett,Tischler, Dirk

, p. 5077 - 5085 (2021/08/16)

Enantioenriched azido alcohols are precursors for valuable chiral aziridines and 1,2-amino alcohols, however their chiral substituted analogues are difficult to access. We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers. A newly isolated two-component flavoprotein styrene monooxygenase StyA proved to be highly selective for epoxidation with a nicotinamide coenzyme biomimetic as a practical reductant. Coupled with azide as a nucleophile for regioselective ring opening, this chemo-enzymatic cascade produced highly enantioenriched aromatic α-azido alcohols with up to >99% conversion. A bi-enzymatic counterpart with halohydrin dehalogenase-catalyzed azidolysis afforded the alternative β-azido alcohol isomers with up to 94% diastereomeric excess. We anticipate our biocatalytic cascade to be a starting point for more practical production of these chiral compounds with two-component flavoprotein monooxygenases.

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