17496-14-9

Basic information

• Product Name: 2-METHYL-1-INDANONE
• Synonyms: 2-METHYLINDAN-1-ONE;2-METHYL-INDANONE;2-METHYL-1-INDANONE;(R,S)-2-Methyl-indan-1-one;2-METHYL-1-INDANONE 97%;2,3-Dihydro-2-methyl-1H-inden-1-one;2-Methyl-2,3-dihydro-1H-inden-1-one;2,3-Dihydro-2-methyl-1H-inden-1-one, 1-Oxo-2-methylindane
• CAS NO: 17496-14-9
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.19
• Product Categories: Indanone & Indene;C10;Carbonyl Compounds;Ketones;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 17496-14-9.mol
• Article Data: 74

Chemical Properties

• Melting Point: 47-47.5 °C
• Boiling Point: 93-95 °C4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Pale yellow liquid
• Density: 1.064 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0426mmHg at 25°C
• Refractive Index: n20/D 1.555(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-METHYL-1-INDANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-1-INDANONE(17496-14-9)
• EPA Substance Registry System: 2-METHYL-1-INDANONE(17496-14-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 23-26-36/37/39-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 17496-14-9(Hazardous Substances Data)

Usage

Description

2-Methyl-1-indanone, a α-benzocycloalkenone, is a derivative of 1-indanone. It is a pale yellow liquid and has been studied for its synthesis, enzymatic dynamic kinetic resolution (DKR), asymmetric α-arylation, and hydroxymethylation. It has also been involved in the synthesis of 2-methyl-6-carboxyazulene.

Uses

Used in Chemical Synthesis:
2-Methyl-1-indanone is used as a starting material for the synthesis of various compounds, including β-benzocycloalkenone, cyclohex-2-en-1-yl 2-methyl-1H-inden-3-yl carbonate, 2-hydroxy-2-methyl-1-indanone, and O-alkoxycarbonylation of lithium enolates. Its application in this field is due to its unique chemical structure and reactivity, which allows for the creation of a wide range of products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Methyl-1-indanone may be utilized in the development of new drugs and medicinal compounds. Its versatility in chemical synthesis and ability to form various derivatives make it a valuable component in the design and synthesis of potential therapeutic agents.
Used in Research and Development:
2-Methyl-1-indanone is also used in research and development settings, where its unique properties and reactivity are explored for potential applications in various fields, including materials science, chemical engineering, and biotechnology. Its study contributes to the advancement of knowledge in these areas and may lead to the discovery of new applications and uses.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 3758, 1981 DOI: 10.1021/jo00331a046Tetrahedron Letters, 29, p. 2183, 1988 DOI: 10.1016/S0040-4039(00)86705-2

InChI:InChI=1/C10H10O/c1-7-6-8-4-2-3-5-9(8)10(7)11/h2-5,7H,6H2,1H3/t7-/m1/s1

Upstream product

• 60-29-7 diethyl ether 
• 925-90-6 ethylmagnesium bromide 
• 1009-67-2 2-methyl-3-phenylpropanoic acid 
• 34917-00-5 2-benzyl-2-methylmalonic acid 
• 57-15-8 1,1,1-trichloro-2-methyl-2-propanol 
• 71-43-2 benzene 
• 117749-63-0 2-benzoyl-2-methyl-indan-1-one 
• 20769-85-1 2-bromoisobutyric acid bromide 
• 824-63-5 2-methylindane 
• 73739-48-7 methyl-2 oxo-1 indane-2 thiolacetate de methyle 
• 83-33-0 inden-1-one 
• 77-78-1 dimethyl sulfate 
• 50-00-0 formaldehyd 
• 93-55-0 1-phenyl-propan-1-one 

Downstream Products

• 857811-68-8 2-methyl-3-phenethyl-indene 
• 5728-91-6 2-bromo-2-methyl-2,3-dihydro-1H-inden-1-one 
• 2852-91-7 (2-carboxyphenyl)acetone 
• 528-46-1 phthalonic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 10489-28-8 2,2-dimethyl-indan-1-one 
• 133571-24-1 2-methyl-1-indanone phenylhydrazone 
• 31883-79-1 3-methyl-3,4-dihydroquinolin-2(1H)-one 
• 2177-47-1 2-Methylindene 
• 136282-00-3 cis-4b,5,9b,10-tetrahydro-8,9b-dimethyl-4b-(4-methylphenylhydrazin-N_b-yl)indeno<1,2-b>indole 
• 157485-24-0 2-methyl-2-isobutenylindan-1-one 
• 25108-48-9 2-(2,4-Dinitro-phenylsulfanyl)-2-methyl-indan-1-one 
• 65870-03-3 3-Phenyl-propionic acid 2-methyl-3H-inden-1-yl ester 
• 65869-97-8 3-(2-methyl-3-phenyl-propionyloxy)-2-methyl-indene 

Relevant articles and documents

ULTRASOUND IN ORGANIC SYNTHESIS 15. RADICAL CYCLISATION OF O-ALLYL BENZAMIDES VIA THE SONOCHEMICALLY GENERATED RADICAL ANIONS

By reaction with lithium metal in THF under sonochemical activation, o-allyl tertiary benzamides are easily cyclised to 2-methylindanone.Yields strongly depend on the substitution pattern of the nitrogen atom.

Novel transformation of 2-substituted alkyl 1-indanone-2-acetates to 6-substituted 3,4-benzotropolones through sequential reduction and oxidation processes using Sm(II) and Ce(IV) salts

When 2-substituted alkyl 1-indanone-2-acetates 1 were treated with samarium diiodide, 3-substituted 2-hydroxy-2,3-methano-1-oxo-1,2,3,4- tetrahydronaphthalenes 4 were obtained. The reaction is proposed to proceed through a rearrangement initiated by intramolecular ketone-ester coupling. Oxidation of these products 4 or their silyl ethers 13 by ceric(IV) ammonium nitrate involving regioselective bond cleavage of their bicyclo[4.1.0]-rings produced the corresponding benzotropolone derivatives 10.

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Ruthenium-Catalyzed Brook Rearrangement Involved Domino Sequence Enabled by Acylsilane-Aldehyde Corporation

A ruthenium-catalyzed [1,2]-Brook rearrangement involved domino sequence is presented to prepare highly functionalized silyloxy indenes with atomic- and step-economy. This domino reaction is triggered by acylsilane-directed C-H activation, and the aldehyde controlled the subsequent enol cyclization/Brook Rearrangement other than β-H elimination. The protocol tolerates a broad substitution pattern, and the further synthetic elaboration of silyloxy indenes allows access to a diverse range of interesting indene and indanone derivatives.

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates

Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.