66309-83-9

Basic information

• Product Name: 1H-Inden-1-one, 2,3-dihydro-2,6-diMethyl-
• Synonyms: 2,6-Dimethyl-1-indanone;1H-Inden-1-one, 2,3-dihydro-2,6-diMethyl-;2,3-Dihydro-2,6-dimethyl-1H-inden-1-one;2,6-DIMETHYL-2,3-DIHYDRO-1H-INDEN-1-ONE
• CAS NO: 66309-83-9
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.21238
• Mol File: 66309-83-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 141-144℃ (17 Torr)
• Appearance: /
• Density: 1.058±0.06 g/cm3(Predicted)
• Vapor Pressure: 0.004-0.26Pa at 20-50℃
• CAS DataBase Reference: 1H-Inden-1-one, 2,3-dihydro-2,6-diMethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Inden-1-one, 2,3-dihydro-2,6-diMethyl-(66309-83-9)
• EPA Substance Registry System: 1H-Inden-1-one, 2,3-dihydro-2,6-diMethyl-(66309-83-9)

Safety Data

• Hazardous Substances Data: 66309-83-9(Hazardous Substances Data)

Usage

General Description

1H-Inden-1-one, 2,3-dihydro-2,6-dimethyl- is a chemical compound with a complex and aromatic structure. It belongs to the class of indenone compounds and contains a 2,3-dihydro-2,6-dimethyl substitution. 1H-Inden-1-one, 2,3-dihydro-2,6-dimethyl- is commonly used in the production of fragrances and perfumes due to its pleasant and unique odor. It is also utilized in various industrial applications as a precursor for the synthesis of other organic compounds. Additionally, it has potential pharmaceutical and medicinal properties, making it a subject of interest for drug development and research. Overall, 1H-Inden-1-one, 2,3-dihydro-2,6-dimethyl- is a versatile and valuable chemical with a wide range of uses in different industries.

Synthetic route

2-methyl-3-p-tolyl-propionyl chloride (860256-66-2) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0 - 10℃; for 3h;	94.6%
With aluminum (III) chloride In dichloromethane at 0℃; for 4h; Heating / reflux;	89%

α-methyl-β-(4-methylphenyl)propionic acid (1012-15-3) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
With polyphosphoric acid at 80℃; for 12h; Friedel-Crafts Acylation;	87%
With PPA at 100℃; for 3h;	1.12 g
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 1 h / 35 - 40 °C 2: aluminum (III) chloride / dichloromethane / 3 h / 0 - 10 °C View Scheme

C11H13ClO → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
With aluminum (III) chloride In 1,2-dichloro-ethane at 80℃; for 4h;	82%

2,5-dimethyl-α-chloropropiophenone (88632-72-8) → 1-(2,5-dimethylphenyl)propan-1-one (35031-52-8) + 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
In tert-butyl alcohol for 16h; Quantum yield; Irradiation; other solvent;	A 6% B 81%

2,6-dimethyl-1H-inden-1-yl acetate → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
With methanol; sodium hydroxide at 20℃; for 24h;	81%

methyl 2-allyl-5-methylbenzoate → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; 1-Phenylethanol; potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In toluene at 100℃; for 16h; Inert atmosphere; Sealed tube;	71%

ethyl cyclopropylcarboxylate (4606-07-9) + toluene (108-88-3) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
aluminium trichloride In toluene Heating;	67%

methanol (67-56-1) + 2,5-dimethyl-α-chloropropiophenone (88632-72-8) → 1-(2,5-dimethylphenyl)propan-1-one (35031-52-8) + 2,6-dimethylindan-1-one (66309-83-9) + 2-(2,5-Dimethyl-phenyl)-propionic acid methyl ester (99356-70-4) + 1-(2-Methoxymethyl-5-methyl-phenyl)-propan-1-one (99356-69-1)

Conditions	Yield
for 16h; Irradiation;	A 4% B 42% C 24% D 28%
for 16h; Quantum yield; Rate constant; Irradiation;	A 4% B 42% C 24% D 28%

2,5-dimethyl-α-chloropropiophenone (88632-72-8) → 1-(2,5-dimethylphenyl)propan-1-one (35031-52-8) + 2,6-dimethylindan-1-one (66309-83-9) + 2-(2,5-Dimethyl-phenyl)-propionic acid methyl ester (99356-70-4) + 1-(2-Methoxymethyl-5-methyl-phenyl)-propan-1-one (99356-69-1)

Conditions	Yield
In methanol for 16h; Irradiation;	A 4% B 42% C 24% D 28%

(+-)-2-methyl-3-p-tolyl-propionic acid-chloride → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
With aluminium trichloride; Petroleum ether anschliessendes Erwaermen;

para-xylene (106-42-3) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / AlCl3 / 0 - 20 °C 2: 42 percent / methanol / 16 h / Irradiation View Scheme

diethyl 2-methyl-2-(4-methylbenzyl)malonate (73120-65-7) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: concd. HCl / acetic acid / 24 h / Heating 2: 1.12 g / polyphosphoric acid / 3 h / 100 °C View Scheme

4-Methylbenzyl bromide (104-81-4) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: K2CO3 / dimethylformamide / 10 h / 150 °C 2: concd. HCl / acetic acid / 24 h / Heating 3: 1.12 g / polyphosphoric acid / 3 h / 100 °C View Scheme

2-methyl-3-p-tolylacrylic acid (25860-59-7) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 7600.51 Torr 2: polyphosphoric acid / 12 h / 80 °C View Scheme

4-methyl-benzaldehyde (104-87-0) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / 0.08 h / 0 °C 1.2: 12 h / 160 - 180 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 7600.51 Torr 3.1: polyphosphoric acid / 12 h / 80 °C View Scheme

4-Methylbenzyl chloride (104-82-5) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium methylate / tetrahydrofuran / 2 h / 50 - 60 °C 1.2: 3 h / 55 - 60 °C 2.1: sodium hydroxide / 3 h / 60 - 65 °C 3.1: thionyl chloride / dichloromethane / 1 h / 35 - 40 °C 4.1: aluminum (III) chloride / dichloromethane / 3 h / 0 - 10 °C View Scheme

methyl 2-methyl-3-(4-methylphenyl)propanoate (29417-79-6) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / 3 h / 60 - 65 °C 2: thionyl chloride / dichloromethane / 1 h / 35 - 40 °C 3: aluminum (III) chloride / dichloromethane / 3 h / 0 - 10 °C View Scheme

2,3-dihydro-6-methyl-1H-inden-1-one (24623-20-9) + methyl iodide (74-88-4) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
Stage #1: 2,3-dihydro-6-methyl-1H-inden-1-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃; Inert atmosphere;

methyl 2-iodo-5-methylbenzoate (103440-52-4) → 2,6-dimethylindan-1-one (66309-83-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / tetrahydrofuran / 12 h / 100 °C / Inert atmosphere; Sealed tube 2: bis(1,5-cyclooctadiene)nickel (0); potassium tert-butylate; potassium phosphate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; 1-Phenylethanol / toluene / 16 h / 100 °C / Inert atmosphere; Sealed tube View Scheme

formaldehyd (50-00-0) + 2,6-dimethylindan-1-one (66309-83-9) → 2-(hydroxymethyl)-2,6-dimethyl-2,3-dihydro-1H-inden-1-one (285977-95-9)

Conditions	Yield
With potassium carbonate In methanol; toluene at 50℃;	97%

2,6-dimethylindan-1-one (66309-83-9) → (1S,2S)-2,6-dimethylindan-1-ol (945613-46-7) + trans-2,6-dimethylindan-1-ol

Conditions	Yield
With formic acid; triethylamine; chloro {[(1S,2S)-(-)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}(mesitylene)ruthenium(II) at 20℃; for 168h;	A 71% B n/a

2,6-dimethylindan-1-one (66309-83-9) + 1-amino-2-propene (107-11-9) → allyl-[(1S,2S)-2,6-dimethy-indan-1-yl]-amine

Conditions	Yield
With formic acid; triethylamine; (S,S)-NH2-CH(Ph)-CH(Ph)-N(Ts)-RuCl-(p-cymene) In dichloromethane at 20℃; for 144h;	60%

2,6-dimethylindan-1-one (66309-83-9) → 7-Bromo-2,6-dimethyl-1-indanone (213381-54-5) + 4,7-dibromo-2,6-dimethyl-1-indanone (940884-61-7) + 4-bromo-2,6-dimethylindan-1-one (892574-45-7)

Conditions	Yield
With aluminum (III) chloride; bromine In chloroform at 0℃; for 3h;	A n/a B 10% C n/a

2,6-dimethylindan-1-one (66309-83-9) + benzylamine (100-46-9) → Benzyl-[2,6-dimethyl-indan-(1Z)-ylidene]-amine

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;

2,6-dimethylindan-1-one (66309-83-9) → C11H13N3

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 71 percent / HCOOH; triethylamine / (S,S)-[RuCl(TsDPEN)(p-cymene)] / 168 h / 20 °C 2.1: diphenylphosphoryl azide / toluene / 0.17 h / 0 °C 2.2: DBU / toluene / 22 h / 0 - 20 °C View Scheme

2,6-dimethylindan-1-one (66309-83-9) → (1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl-amine (752984-24-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 71 percent / HCOOH; triethylamine / (S,S)-[RuCl(TsDPEN)(p-cymene)] / 168 h / 20 °C 2.1: diphenylphosphoryl azide / toluene / 0.17 h / 0 °C 2.2: DBU / toluene / 22 h / 0 - 20 °C 3.1: 232 mg / Ph3P; H2O / tetrahydrofuran / Heating View Scheme

2,6-dimethylindan-1-one (66309-83-9) → C18H19NO

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 71 percent / HCOOH; triethylamine / (S,S)-[RuCl(TsDPEN)(p-cymene)] / 168 h / 20 °C 2.1: diphenylphosphoryl azide / toluene / 0.17 h / 0 °C 2.2: DBU / toluene / 22 h / 0 - 20 °C 3.1: 232 mg / Ph3P; H2O / tetrahydrofuran / Heating 4.1: 86 percent / triethylamine / CH2Cl2 View Scheme

2,6-dimethylindan-1-one (66309-83-9) → (+)-(2S)-2,3-dihydro-2,5-dimethyl-1H-indene-2-methanol (285977-87-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / K2CO3 / toluene; methanol / 50 °C 2: MeSO3H; H2 / Pd/C / propan-2-ol / 7.5 h / 80 °C / 2250.18 Torr 3: 6.39 g / ethanol; various solvent(s) View Scheme

2,6-dimethylindan-1-one (66309-83-9) → (-)-(2R)-2,3-dihydro-2,5-dimethyl-1H-indene-2-methanol

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / K2CO3 / toluene; methanol / 50 °C 2: MeSO3H; H2 / Pd/C / propan-2-ol / 7.5 h / 80 °C / 2250.18 Torr 3: 6.15 g / ethanol; various solvent(s) View Scheme

2,6-dimethylindan-1-one (66309-83-9) → (+/-)-2,3-dihydro-2,5-dimethyl-1H-indene-2-methanol (285977-85-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / K2CO3 / toluene; methanol / 50 °C 2: MeSO3H; H2 / Pd/C / propan-2-ol / 7.5 h / 80 °C / 2250.18 Torr View Scheme

2,6-dimethylindan-1-one (66309-83-9) → benzyl-[(1S,2S)-2,6-dimethyl-indan-1-yl]-amine

Conditions	Yield
Multi-step reaction with 2 steps 1: p-TsOH / toluene / Heating 2: HCOOH; Et3N / (S,S)-NH2-CH(Ph)-CH(Ph)-N(Ts)-RuCl-(p-cymene) complex / CH2Cl2 / 144 h / 20 °C View Scheme

2,6-dimethylindan-1-one (66309-83-9) → [(2S)-2,3-dihydro-2,5-dimethyl-1H-inden-2-yl]methyl-(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate

Conditions	Yield
Multi-step reaction with 4 steps 1: 97 percent / K2CO3 / toluene; methanol / 50 °C 2: MeSO3H; H2 / Pd/C / propan-2-ol / 7.5 h / 80 °C / 2250.18 Torr 3: 6.39 g / ethanol; various solvent(s) 4: 61 percent / pyridine / 20 °C View Scheme

2,6-dimethylindan-1-one (66309-83-9) → 2-(hydroxymethyl)-2,6-dimethyl-2,3-dihydro-1H-inden-1-one (285977-95-9)

Conditions	Yield
With potassium carbonate In water; toluene

formaldehyd (50-00-0) + 2,6-dimethylindan-1-one (66309-83-9) → (S)-2,3-dihydro-2-(hydroxymehtyl)-2,6-dimethylindane-1-one (1073511-12-2) + (R)-2,3-dihydro-2-(hydroxymethyl)-2,6-dimethylindane-1-one (1073511-11-1)

Conditions	Yield
With pyridine; C23H40N4O4; scandium tris(trifluoromethanesulfonate) In water at 20℃; for 24h; enantioselective reaction;

2,6-dimethylindan-1-one (66309-83-9) → ethyl 2-(2,5-dimethyl-1H-inden-3-yl)acetate (1430230-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 1.2: 4 h / -78 °C 2.1: acetic acid; sulfuric acid / 4 h / 20 °C View Scheme

Upstream product

• 1012-15-3 α-methyl-β-(4-methylphenyl)propionic acid 
• 103440-52-4 methyl 2-iodo-5-methylbenzoate 
• 24623-20-9 2,3-dihydro-6-methyl-1H-inden-1-one 
• 74-88-4 methyl iodide 
• 29417-79-6 methyl 2-methyl-3-(4-methylphenyl)propanoate 
• 104-82-5 4-Methylbenzyl chloride 
• 104-87-0 4-methyl-benzaldehyde 
• 25860-59-7 2-methyl-3-p-tolylacrylic acid 
• 104-81-4 4-Methylbenzyl bromide 
• 73120-65-7 diethyl 2-methyl-2-(4-methylbenzyl)malonate 
• 106-42-3 para-xylene 
• 860256-66-2 2-methyl-3-p-tolyl-propionyl chloride 
• 4606-07-9 ethyl cyclopropylcarboxylate 
• 108-88-3 toluene 

Downstream Products

• 1346513-35-6 C₂₃H₂₄O₂ 
• 66703-26-2 2,3,5-trimethyl-1H-indene 

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