83-33-0

Basic information

• Product Name: 1-Indanone
• Synonyms: alpha-indanone;Hydrindone;r-Hydrindone;alpha-hydrindone;1H-Inden-1-one, 2,3-dihydro-;2,3-dihydroinden-1-one;1H-Inden-1-one,2,3-dihydro-;Indanone (VAN);Indan-1-one;1-Indone;2,3-Dihydro-1H-inden-1-one;1-Indanone(1H-Inden-1-one,2,3-dihydro-)
• CAS NO: 83-33-0
• Molecular Formula: C₉H₈O
• Molecular Weight: 132.15922
• EINECS: 201-470-1
• Mol File: 83-33-0.mol
• Article Data: 366

Chemical Properties

• Melting Point: 38-42℃
• Boiling Point: 244 °C at 760 mmHg
• Flash Point: 111.7 °C
• Appearance: pale yellow liquid
• Density: 1.148 g/cm³
• Water Solubility: 6.5 g/L (20 C)
• CAS DataBase Reference: 1-Indanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Indanone(83-33-0)
• EPA Substance Registry System: 1-Indanone(83-33-0)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:
• Hazardous Substances Data: 83-33-0(Hazardous Substances Data)

Usage

General Description

1-Indanone, also known as alpha-Indanone and indan-1-one, is a chemical compound classified as a ketone. Its molecular formula is C9H8O, indicating it consists of nine carbon atoms, eight hydrogen atoms, and one oxygen atom. This organic compound is found as a white to light yellow crystalline solid in its pure form. It exhibits an aromatic, sweet floral scent and is an essential intermediate in the preparation of numerous pharmaceutical and agrochemical products. It's also used in the perfume industry due to its unique odor properties. It's important to handle this chemical with caution as it may be harmful if inhaled, swallowed, or comes into contact with skin, and may cause eye irritation.

InChI:InChI=1/C9H8O/c10-9-6-5-7-3-1-2-4-8(7)9/h1-4H,5-6H2

Synthetic route

3-Phenylpropionic acid (501-52-0) → inden-1-one (83-33-0)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 80℃; for 3h; Friedel-Crafts Acylation; High pressure; Inert atmosphere; Green chemistry;	100%
With trifluorormethanesulfonic acid at 5 - 20℃; for 2h; Cyclization;	99%
With polyphosphoric acid at 90℃; for 0.5h;	98.2%

indan-1-one oxime (68253-35-0, 100485-57-2, 3349-60-8) → inden-1-one (83-33-0)

Conditions	Yield
With potassium permanganate; tungstate sulfuric acid In dichloromethane; water at 20℃; for 0.133333h;	94%
With diphenyl ditelluride; oxygen In ethyl acetate for 24h; Irradiation;	94%
With water; 2-nitro-4,5-dichloropyridazin-3(2H)-one In methanol at 150℃; under 10336 Torr; for 0.166667h; Microwave irradiation;	90%

1-Indanol (6351-10-6) → inden-1-one (83-33-0)

Conditions	Yield
With iodosylbenzene; potassium bromide In water for 2h; Oxidation;	100%
With cerium(III) sulfate; barium bromate In water; acetonitrile for 2h; Heating;	100%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate at 80℃;	100%

1-indene (95-13-6) → inden-1-one (83-33-0)

Conditions	Yield
With dihydrogen peroxide In water at 75℃; for 12h;	100%
With tert.-butylhydroperoxide; C21H19N5Pd(2+)*2BF4(1-) In decane; acetonitrile at 70℃; for 24h; Temperature; Wacker Oxidation;	95%
With iron(II) chloride In ethanol at 80℃; for 6h;	93%

INDANE (496-11-7) → inden-1-one (83-33-0)

Conditions	Yield
With tert.-butylhydroperoxide; C24H18N6O3*Cu(1+)*I(1-) In water at 20℃; for 4h; Reagent/catalyst;	98%
With tert.-butylhydroperoxide; copper(II) choride dihydrate; tetrabutyl-ammonium chloride; sodium carbonate; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 20℃; for 17h; Green chemistry;	98%
With tert.-butylhydroperoxide; 0.5C34H18N16(4-)*2H2O*2Cu(1+)*C3H7NO In water at 20℃; for 4h; Reagent/catalyst; Sonication;	97%

3-Phenylpropionic acid (501-52-0) → C18H16O2 + inden-1-one (83-33-0)

Conditions	Yield
Stage #1: 3-Phenylpropionic acid With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h; Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 0.5h;	A n/a B 94%
Stage #1: 3-Phenylpropionic acid With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h; Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 2h;	A 75% B 16%

1,7-diphenyl-4-oxahepta-1,6-diyne (13225-61-1) → inden-1-one (83-33-0)

Conditions	Yield
With water; PtCl4-CO In tetrahydrofuran at 80℃; under 1034.3 Torr; for 1.5h;	94%

carbon monoxide (201230-82-2) + o-iodostyrene (4840-91-9) → inden-1-one (83-33-0)

Conditions	Yield
With pyridine; palladium diacetate; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 100℃; under 760 Torr; for 8h;	100%

3-Bromoindan-1-one (40774-41-2) → inden-1-one (83-33-0)

Conditions	Yield
With water; zinc In acetonitrile at 25℃; for 6h; Sealed tube; Inert atmosphere;	62%
With water; zinc In acetonitrile at 25℃; for 6h; Inert atmosphere; Sealed tube;	62%

1-Indanol (6351-10-6) → (R)-indan-1-ol (697-64-3) + (S)-indanol (25501-32-0) + inden-1-one (83-33-0)

Conditions	Yield
With palladium dichloro (η-2,5-norbornadiene); oxygen; (-)-sparteine In toluene at 60℃; for 54h; Title compound not separated from byproducts;	A n/a B n/a C 63%
With 3 A molecular sieve; oxygen; (-)-sparteine; palladium dichloro (η-2,5-norbornadiene) In toluene at 60℃; under 760 Torr; for 54h;	A n/a B n/a C 63%
With (1R)-N-oxyl-1-(N-benzylcarbamoyl)-8-azabicyclo[3.2.1]octane; sodium hydrogencarbonate; sodium bromide In dichloromethane; water at 0℃; Electrochemical reaction; optical yield given as %ee; enantioselective reaction;	A n/a B n/a C 53%

INDANE (496-11-7) → 1-Indanol (6351-10-6) + inden-1-one (83-33-0)

Conditions	Yield
With N-hydroxyphthalimide; oxygen; butane-2,3-dione dioxime In acetonitrile at 80℃; under 3750.38 Torr; for 8h;	A 10.4% B 75.3%
With N-hydroxyphthalimide; 1,4-diamino-2,3-dichloroanthraquinone; oxygen In acetonitrile at 80℃; under 1875.15 - 2250.18 Torr; for 6h;	A 15 % Chromat. B 64%
With 1H-imidazole; sodium periodate; Mn(TDCPP)OAc In dichloromethane for 24h; Ambient temperature;	A 26% B 60%

2-(phenylthio)-2,3-dihydro-1H-inden-1-one (78196-99-3) → inden-1-one (83-33-0) + diphenyldisulfane (882-33-7)

Conditions	Yield
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Irradiation; chemoselective reaction;	A 36% B 25%

carbon monoxide (201230-82-2) + 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1) → inden-1-one (83-33-0)

Conditions	Yield
With water; triethylamine; triphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer In tetrahydrofuran at 160℃; under 51485.6 Torr; for 4h;	61%

1H-inden-3-yl acetate (19455-83-5) → inden-1-one (83-33-0) + (R)-1-indanyl acetate (879-35-6)

Conditions	Yield
With Novozym 435; 2,6-dimethyl-4-heptanol; (Ph4C4CO)2H(μ-H)(CO)4Ru2 In toluene at 70℃; for 72h; Reduction; Enzymatic reaction;	A 13 % Spectr. B 85%

1-hydroxy-2,3-dihydro-1H-indene-1-carboxylic acid → inden-1-one (83-33-0)

Conditions	Yield
With diethylamino-sulfur trifluoride In dichloromethane at -78 - 20℃; for 4.5h; Inert atmosphere;	37%

2-(hydroxy-p-tolyl-methylene)indan-1-one → inden-1-one (83-33-0)

Conditions	Yield
With indium(III) triflate In butan-1-ol for 6h; Solvent; Reflux;	86%

2-(hydroxy-o-tolyl-methylene)indan-1-one → inden-1-one (83-33-0)

Conditions	Yield
With indium(III) triflate In butan-1-ol for 6h; Reflux;	88%

2-[hydroxy-(4-methoxyphenyl)methylene]indan-1-one → inden-1-one (83-33-0)

Conditions	Yield
With indium(III) triflate In butan-1-ol for 12h; Reflux;	85%

2-[(4-chlorophenyl)hydroxymethylene]indan-1-one → inden-1-one (83-33-0)

Conditions	Yield
With indium(III) triflate In butan-1-ol for 6h; Reflux;	90%

2-(hydroxypyridin-3-yl-methylene)indan-1-one → inden-1-one (83-33-0)

Conditions	Yield
With indium(III) triflate In butan-1-ol for 4h; Reflux;	86%

2-vinylbenzaldehyde (28272-96-0) → inden-1-one (83-33-0)

Conditions	Yield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine In toluene at 150℃; for 1h; Inert atmosphere;	97%
With acetic acid; L-proline at 120℃; for 24h; Green chemistry;	45%
(iPrO)Ti(μ:η1,η1-OCMe2CH2PPh2)RhCl In dichloromethane at 25℃; for 11h;	40%

1-(1-ethoxyethoxy)indene → inden-1-one (83-33-0)

Conditions	Yield
With sodium carbonate; acetic acid In methanol; water	82.4%

2-bromostyrene (2039-88-5) + molybdenum hexacarbonyl → inden-1-one (83-33-0)

Conditions	Yield
With pyridine; tetrabutyl-ammonium chloride; tri tert-butylphosphoniumtetrafluoroborate; palladium diacetate In 1,4-dioxane at 150℃; for 0.333333h; microwave irradiation;	75%

(E)-2,3-dihydro-1H-inden-1-one O-acetyloxime → (S)-1-Aminoindane (10277-74-4, 34698-41-4, 61341-86-4, 61949-83-5) + (R)-1-Aminoindane (10277-74-4) + inden-1-one (83-33-0)

Conditions	Yield
With [Rh(OH)(cod)]2; Ureaphos-2; hydrogen; caesium carbonate In isopropyl alcohol at 55℃; under 97509.8 Torr; for 17h; Reagent/catalyst; Schlenk technique; Autoclave; Optical yield = < 2 %ee;	A n/a B n/a C 6 %Chromat.

1-Indanol (6351-10-6) → (S)-indanol (25501-32-0) + inden-1-one (83-33-0)

Conditions	Yield
With sodium hydrogencarbonate; sodium bromide; chiral azabicyclo-N-oxyl In dichloromethane at 0℃; Electrochemical reaction;	A n/a B 52%
With C32H36IrNO2S In cyclohexanone at 30℃; for 7h; optical yield given as %ee; enantioselective reaction;	A 50% B n/a
With C50H42ClN2O3Ru In chloroform at 25℃; Kinetics; Time; Reagent/catalyst; Molecular sieve; Resolution of racemate; enantioselective reaction;	A 33.7% B n/a

2-vinylbenzoic acid (27326-43-8) → inden-1-one (83-33-0)

Conditions	Yield
With potassium phosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane; dimethyl dicarbonate In acetonitrile at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; Sealed tube;	76%
Multi-step reaction with 2 steps 1: 56 percent / tributylphosphine / CH2Cl2 / 4 h / -30 °C 2: 56 percent / Bu3SnH; AIBN / benzene / 10 h / Heating View Scheme

3-(4-methoxyphenyl)-2-methylpropionic acid (52427-11-9) → 6-methoxy-2-methylindanone (5464-10-8) + inden-1-one (83-33-0)

Conditions	Yield
With PPA
With PPA
With PPA In (2S)-N-methyl-1-phenylpropan-2-amine hydrate
With PPA
With PPA

carbon monoxide (201230-82-2) + 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1) → 3-phenyl-propionaldehyde (104-53-0) + 2-Phenyl-3-(trimethylsilyl)-propanal (59556-86-4) + inden-1-one (83-33-0)

Conditions	Yield
With hydrogen; triethylamine; triphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer In tetrahydrofuran at 160℃; under 36775.4 Torr; for 4h;	A 25% B 36% C 10%

1-indene (95-13-6) → 1-indanyl hydroperoxide (92799-73-0) + inden-1-one (83-33-0)

Conditions	Yield
With triethylsilane; oxygen; [5,10,15,20-tetrakis(2,6-dichlorophenyl)porphinato]cobalt(II) In dichloromethane; isopropyl alcohol at 28℃; under 760 Torr; for 1.5h;	A 60% B n/a

Indan-1-carboxylic acid (14381-42-1) → inden-1-one (83-33-0)

Conditions	Yield
With (2,2'-dipyridyl)bis(5-methyl-2-(4-fluoro)phenylpyridine-N,C)iridium(III) hexafluorophosphate; oxygen; sodium carbonate; 1,1'-diethyl-4,4'-bipyridinium diperchlorate In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 16h; Irradiation;	77%
With iron(III) chloride; oxygen In N,N-dimethyl-formamide at 110℃;	49%

inden-1-one (83-33-0) → truxene (548-35-6)

Conditions	Yield
With hydrogenchloride; acetic acid In water at 100℃; for 16h;	100%
With hydrogenchloride; acetic acid at 100℃; for 16h;	98%
With hydrogenchloride; acetic acid In water at 120℃; for 10h;	90%

inden-1-one (83-33-0) → 1-Indanol (6351-10-6)

Conditions	Yield
With 15percent aqueous acidic TiCl3; 30percent aqueous NH3 In methanol at 0 - 20℃; for 0.0833333h;	100%
With sodium tetrahydroborate	99%
With C15H18BF3; hydrogen; tert-butylimino-tri(pyrrolidino)phosphorane In tetrahydrofuran at 75℃; under 75007.5 Torr; for 20h; Glovebox;	99%

inden-1-one (83-33-0) → indan-1-one oxime (68253-35-0, 100485-57-2, 3349-60-8)

Conditions	Yield
With hydroxylamine hydrochloride	100%
With hydroxylamine hydrochloride In ethanol at 20 - 25℃; for 0.166667h;	91.6%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol at 20 - 25℃; for 1h;	91.6%

inden-1-one (83-33-0) → (S)-indanol (25501-32-0)

Conditions	Yield
With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 0℃; for 0.5h; enantioselective reaction;	100%
With formic acid; [RuCl2(hexamethylbenzene)]2; (S)-2-piperidinemethanethiol hydrochloride; triethylamine at 30℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%
With formic acid; triethylamine at 28℃; for 48h; enantioselective reaction;	99%

1-amino-buten-1-en-3-one (2801-93-6) + inden-1-one (83-33-0) → 3-methyl-4-azafluorene (18631-19-1)

Conditions	Yield
With acetic acid at 120℃; for 20h;	100%

inden-1-one (83-33-0) → (R)-indan-1-ol (697-64-3)

Conditions	Yield
With (1R,2R)-PhCH(NH2)CH(Ph)NH-p-SO2-C6H4-CH2CH2-silica gel; tetrabutylammomium bromide; sodium formate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 at 40℃;	100%
With dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 0℃; for 0.5h; enantioselective reaction;	100%
With formic acid; C38H40ClN2O2RhS; triethylamine In neat (no solvent) at 24 - 30℃; for 5h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;	100%

inden-1-one (83-33-0) + benzyl alcohol (100-51-6) → 2-benzyl-1-indanone (16307-30-5)

Conditions	Yield
With titanium(IV) oxide; potassium hydroxide In toluene at 100℃; for 10h; Sealed tube; Irradiation;	100%
With dichloro[1,3‐diethyl(5,6‐dimethyl)benzimidazolin‐2‐ylidene](benzene)ruthenium (II); sodium hydroxide In toluene at 105℃; for 8h;	88%
With bis(μ-chloro)-bis[1,3-di(2-pyridyl)-4,6-dimethylbenzene-N,C(2'),N-iridium chloride]; caesium carbonate In tert-Amyl alcohol for 12h; Reflux;	87%

ethyl trifluoroacetate, (383-63-1) + inden-1-one (83-33-0) → lithium 3-(trifluoroacetyl)indanonate

Conditions	Yield
With ethanol; lithium hydride In benzene Reflux; Inert atmosphere;	100%

inden-1-one (83-33-0) + 2,2-dihydroxyacetic acid (563-96-2) → 1-oxoindan-Δ2,α-acetic acid (114915-75-2)

Conditions	Yield
With sulfuric acid Inert atmosphere;	100%

3-pyridinecarboxaldehyde (500-22-1) + inden-1-one (83-33-0) → 2-(pyridin-3-ylmethylene)-2,3-dihydro-1H-inden-1-one (4875-90-5)

Conditions	Yield
With sodium hydroxide In ethanol; water at 0℃; Claisen-Schmidt Condensation;	99.8%
With sodium hydroxide In methanol at 20℃; for 12h;

3-pyridinecarboxaldehyde (500-22-1) + inden-1-one (83-33-0) → (2E)-2-(pyridin-3-ylmethylidene)-2,3-dihydro-1H-inden-1-one (4875-90-5)

Conditions	Yield
Stage #1: 3-pyridinecarboxaldehyde; inden-1-one In ethanol for 0.0833333h; Inert atmosphere; Stage #2: With sodium hydroxide In ethanol; water for 0.5h; Inert atmosphere;	99.8%
With sodium hydroxide In ethanol; water at 0℃; Claisen-Schmidt Condensation;	73%
In methanol at 20℃; Alkaline conditions;	29%

3-Chlorobenzaldehyde (587-04-2) + inden-1-one (83-33-0) → (E)-2-(4-chlorobenzylidene)-indan-1-one (5706-17-2)

Conditions	Yield
Stage #1: m-Chlorobenzaldehyde; inden-1-one In ethanol for 0.0833333h; Inert atmosphere; Stage #2: With sodium hydroxide In ethanol; water for 0.5h; Inert atmosphere;	99.7%

pyridine-4-carbaldehyde (872-85-5) + inden-1-one (83-33-0) → (E)-2-(pyridin-4-ylmethylene)-2,3-dihydro-1H-inden-1-one (4875-89-2)

Conditions	Yield
Stage #1: pyridine-4-carbaldehyde; inden-1-one In ethanol for 0.0833333h; Inert atmosphere; Stage #2: With sodium hydroxide In ethanol; water for 0.5h; Inert atmosphere;	99.4%
With piperidine; acetic acid at 130℃; for 1.5h;	34%

pyridine-4-carbaldehyde (872-85-5) + inden-1-one (83-33-0) → 2-(pyridin-4-ylmethylene)-2,3-dihydro-1H-inden-1-one (4875-89-2)

Conditions	Yield
With sodium hydroxide In ethanol; water at 0℃; Claisen-Schmidt Condensation;	99.4%

2-chloro-benzaldehyde (89-98-5) + inden-1-one (83-33-0) → (E)-2-(2-chlorobenzylidene)-2,3-dihydro-1H-inden-1-one (103457-37-0)

Conditions	Yield
Stage #1: 2-chloro-benzaldehyde; inden-1-one In ethanol for 0.0833333h; Inert atmosphere; Stage #2: With sodium hydroxide In ethanol; water for 0.5h; Inert atmosphere;	99.2%
With sodium hydroxide In ethanol for 3h;	84%

inden-1-one (83-33-0) + 2,4-Dimethoxybenzaldehyde (613-45-6) → (E)-2-(2,4-dimethoxybenzyliden)-2,3-dihydro-1H-inden-1-one

Conditions	Yield
With hydrogenchloride; acetic acid at 20℃; for 24h;	99.1%
basic condition;
Claisen-Schmidt Condensation; Alkaline conditions;

inden-1-one (83-33-0) + methyl iodide (74-88-4) → 2,2-dimethyl-indan-1-one (10489-28-8)

Conditions	Yield
Stage #1: inden-1-one With sodium hydride In N,N-dimethyl-formamide for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide for 1.5h;	99%
Stage #1: inden-1-one With sodium hydride In 1,2-dimethoxyethane at 10 - 35℃; for 0.166667h; Stage #2: methyl iodide In 1,2-dimethoxyethane at 10 - 35℃; for 1h;	99%
Stage #1: inden-1-one With sodium hydride In 1,2-dimethoxyethane at 20℃; for 0.166667h; Stage #2: methyl iodide In 1,2-dimethoxyethane at 20℃; for 1h;	99%

inden-1-one (83-33-0) → 2,2-dibromoindan-1-one (7749-02-2)

Conditions	Yield
With N-Bromosuccinimide; toluene-4-sulfonic acid at 80℃; for 1h;	99%
With bromine In acetic acid at 100℃; for 0.75h;	97%
With hydrogen bromide; dihydrogen peroxide In methanol; water for 20h; Heating;	89%

inden-1-one (83-33-0) → 2-bromoindanone (1775-27-5)

Conditions	Yield
	99%
With bromine In diethyl ether Cooling with ice;	99%
With copper bromide In chloroform; ethyl acetate for 1h; Reflux;	96%

trimethylsilyl cyanide (7677-24-9) + inden-1-one (83-33-0) → 1-((trimethylsilyl)oxy)-2,3-dihydro-1H-indene-1-carbonitrile (31928-65-1)

Conditions	Yield
With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 18h;	99%
Stage #1: inden-1-one With scandium tris(trifluoromethanesulfonate); 1-n-butyl-3-methylimidazolium hexafluoroantimonate at 20℃; for 0.166667h; Stage #2: trimethylsilyl cyanide at 20℃; for 2h; Inert atmosphere;	99%
With C29H46LaN3Si2 at 15℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique;	99%

inden-1-one (83-33-0) + carbonic acid dimethyl ester (616-38-6) → methyl 1-indanone-2-carboxylate (22955-77-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	99%
With sodium hydride In toluene; mineral oil at 0 - 120℃; for 18h;	95%
With sodium hydride In tetrahydrofuran; mineral oil for 2h; Reflux; Inert atmosphere;	93%

inden-1-one (83-33-0) → (R)-indan-1-ol (697-64-3) + (S)-indanol (25501-32-0)

Conditions	Yield
With dimethylsulfide borane complex; (S)-2-(anilinodiphenylmethyl)pyrrolidine In tetrahydrofuran at 20℃; for 2h; enantioselective reaction;	A 99% B n/a
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 2h; enantioselective reaction;	A 96% B n/a
With sprouted Pisum sativa In water at 25℃; for 58h; optical yield given as %ee; enantioselective reaction;	A n/a B 42%

N,N-dimethyl acetamide (127-19-5) + inden-1-one (83-33-0) → 2-acetoxyindan-1-one (1579-15-3)

Conditions	Yield
Stage #1: N,N-dimethyl acetamide; inden-1-one With trifluorormethanesulfonic acid; thallium(III) acetate at 60℃; for 0.333333h; Stage #2: With water for 0.166667h; Further stages.;	99%

inden-1-one (83-33-0) → β-bromoindenone (90271-93-5)

Conditions	Yield
Stage #1: inden-1-one With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2h; Heating; irradiation; Stage #2: With triethylamine In tetrachloromethane at 0 - 20℃; for 12h;	99%
Stage #1: inden-1-one With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2h; Photolysis; Reflux; Stage #2: With triethylamine In tetrachloromethane at 0℃; for 9h;	95%
Stage #1: inden-1-one With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2.5h; Reflux; Stage #2: With triethylamine In tetrachloromethane at 0℃;	85%

lithium bis isopropoxyamide (LDA) + N-(tert-butyl)-N-(1-chloro-1,1-dimethylsilyl)amine (60556-33-4) + inden-1-one (83-33-0) → N-(tert-butyl)-N-(1-(1H-3-indenyloxy)-1,1-dimethylsilyl)amine (308846-97-1)

Conditions	Yield
In tetrahydrofuran	99%

Upstream product

• 5962-03-8 thioisochromen-1-one 
• 4361-85-7 1-oxo-1H-isothiochromene-3-carboxylic acid 
• 64-17-5 ethanol 
• 19598-01-7 cis-2-chloroindan-1-ol 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 35275-62-8 1-chloroindane 
• 35116-20-2 1-Indenylacetate 
• 78386-35-3 ethyl-(2-bromo-indan-1-yl)-ether 
• 10277-36-8 (1-oxo-indan-2-yl)-glyoxylic acid 
• 195067-13-1 3-Aminoinden-2-carbonsaeureethylester 
• 100-66-3 methoxybenzene 
• 541-88-8 Chloroacetic anhydride 
• 501-52-0 3-Phenylpropionic acid 

Downstream Products

• 54752-43-1 2-piperonylidene-indan-1-one 
• 5350-68-5 2-acetylindan-1-one 
• 103457-37-0 (E)-2-(2-chlorobenzylidene)-2,3-dihydro-1H-inden-1-one 
• 51813-42-4 2-[4,5-dimethoxy-2-nitro-benzylidene-(seqtrans)]-indan-1-one 
• 5706-12-7 2-benzylidine-1-indanone 
• 124996-01-6 2-(4-hydroxybenzylidene)-2, 3-dihydro-1H-inden-1-one 
• 17434-24-1 2-(4-methoxybenzylidene)-2,3-dihydro-1H-inden-1-one 
• 5706-14-9 2-[(E)-4-methoxyphenylmethylidene]-1-indanone 
• 23418-53-3 2-(o-hydroxybenzylidene)indenone 
• 109857-09-2 <(hydroxy-4 methoxy-3 phenyl) methylene>-2 indanone-1 
• 5706-15-0 2-(3′′,4′′-dimethoxybenzylidene)indan-1-one 
• 243-51-6 11H-indeno[1,2-b]quinoline 
• 51813-43-5 2-(2-amino-benzylidene)-indan-1-one 
• 108975-85-5 N-phenethyl-2,3-dihydro-1H-inden-1-amine 

Relevant articles and documents

Photoinduced Double Addition of Acetylene to 3-Oxocyclopent-1-ene-1-carbonitrile or 3-Oxocyclopent-1-enyl Acetate Leading to 2,3-Dihydro-1H-inden-1-one and Other Rearranged Products

UV Irradiation of 3-oxocyclopent-1-enyl acetate (17) and acetylene in MeCN at 0 deg C gives, besides the product of normal enone-alkyne cycloaddition (cis-4-oxobicyclohept-6-en-1-yl acetate, 18) and its product of oxa-di-?-methane rearrangement (5-oxotricyclo2,7>hept-2-yl acetate, 19), unexpected products of further addition of a molar equivalent of acetylene.These are indanone (= 2,3-dihydro-1H-inden-1-one, 16), in 21percent yield, cis-1-cisoid-1,2-cis-2- (20) and cis-1-transoid-1,2-cis-2,7-oxotricyclo2,5>non-3-en-1-yl acetate (21), 4-oxo-7-'exo'-vinyltricyclo2,6>hept-2-yl acetate (22), cis-4-oxo-6 -'endo'- (23) and cis-4-oxo-6-'exo'-vinylbicyclohept-1-yl acetate (24), and cis-4-oxo-7-'exo'-vinylbicyclohept-1-yl acetate (25).At least in part, indanone must be formed via intermediates 20 and 21.In fact, on heating a 9:1 mixture 20/21, indanone is obtained quantitatively.With 3-oxocyclopent-1-ene-1-carbonitrile (15) in place of 17, indanone is formed in lower (8percent) yield besides much tars.

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Covalent Linkage of an R-ω-Transaminase to a d-Amino Acid Oxidase through Protein Splicing to Enhance Enzymatic Catalysis of Transamination

R-ω-Transaminases (RTAs) catalyse the conversion of R-configured amines [e.g., (R)-1-phenylethylamine] into the corresponding ketones (e.g., acetophenone), by transferring an amino group from an amino donor [e.g., (R)-1-phenylethylamine] onto an amino acceptor (e.g., pyruvate), resulting in a co-product (e.g., d-alanine). d-Alanine can be deaminated back to pyruvate by d-amino acid oxidase (DAAOs). Here, through in vivo subunit splicing, the N terminus of an RTA subunit (RTAS) was specifically ligated to the C terminus of a DAAO subunit (DAAOS) through native peptide bonds (RTA&DAAO). RTAS is in close proximity to DAAOS, at a molecular-scale distance. Thus the transfer of pyruvate and d-alanine between RTA and DAAO can be directional and efficient. Pyruvate→d-alanine→pyruvate cycles are efficiently formed, thus promoting the forward transamination reaction. In a different, in vitro noncovalent approach, based on coiled-coil association, the RTAS N terminus was specifically associated with the DAAOS C terminus (RTA#DAAO). In addition, the two mixed individual enzymes (RTA+DAAO) were also studied. RTA&DAAO has a shorter distance between the paired subunits (RTAS–DAAOS) than RTA#DAAO, and the number of the paired subunits is higher than in the case of RTA#DAAO, whereas RTA+DAAO cannot form the paired subunits. RTA&DAAO exhibited a transamination catalysis efficiency higher than that of RTA#DAAO and much higher than that of RTA+DAAO.

Improved synthetic route to methyl 1-fluoroindan-1-carboxylate (FICA Me ester) and 4-methyl derivatives

An improved synthetic route has been developed for the preparation of methyl 1-fluoroindan-1-carboxylate (FICA Me ester) from 1-indanone. Methyl 4-methyl-1-fluoroindan-1-carboxylate (4-Me-FICA Me ester) was also prepared following the same procedure.

Selective Aerobic Oxidation of Secondary C (sp3)-H Bonds with NHPI/CAN Catalytic System

Abstract: The direct aerobic oxidation of secondarty C(sp3)-H bonds was achieved in the presence of N-hydroxyphthalimide (NHPI) and cerium ammonium nitrate (CAN) under mild conditions. Various benzylic methylenes could be oxidized to carbonyl compounds in satisfied selectivity while saturated cyclic alkanes could be further oxidized to the corresponding lactones with the catalytic system. Remarkably, 25% of isochroman was converted to corresponding ketone with a selectivity of 96%. The reaction was initiated by hydrogen atom abstraction from NHPI by cerium and nitrates under oxygen atmosphere to form PINO radicals. 2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO) addition experiments showed that the oxidation proceeded via a complex radical chain mechanism and an ion pathway. Graphic Abstract: [Figure not available: see fulltext.]

Catalytic Aerobic Oxidation of Alkenes with Ferric Boroperoxo Porphyrin Complex; Reduction of Oxygen by Iron Porphyrin

We herein describe the development of a mild and selective catalytic aerobic oxidation process of olefins. This catalytic aerobic oxidation reaction was designed based on experimental and spectroscopic evidence assessing the reduction of atmospheric oxygen using a ferric porphyrin complex and pinacolborane to form a ferric boroperoxo porphyrin complex as an oxidizing species. The ferric boroperoxo porphyrin complex can be utilized as an in-situ generated intermediate in the catalytic aerobic oxidation of alkenes under ambient conditions to form oxidation products that differ from those obtained using previously reported ferric porphyrin catalysis. Moreover, the mild reaction conditions allow chemoselective oxidation to be achieved.