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

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

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 
• 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 
• 242484-64-6 (R)-2-fluoro-2-methyl-1-indanone 
• 242484-64-6 (S)-2-fluoro-2-methyl-1-indanone 

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.

Kinetic and Theoretical Studies on Ni0/N-Heterocyclic Carbene-Catalyzed Intramolecular Alkene Hydroacylation

A combined kinetic and theoretical study was conducted in order to clarify the details on the reaction mechanism for Ni0/ItBu-catalyzed intramolecular alkene hydroacylation. The results confirm the hypothesis that this intramolecular hydroacylation proceeds through an oxanickelacycle key intermediate.

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.

REDUCTION PAR LE BOROHYDRURE DE SODIUM D'INDANONES CHROME TRICARBONYLE ENDO SUBSTITUEES EN α ET β. POSITION DE L'ETAT DE TRANSITION ET FACTEURS DE REACTIVITE

In the indanone Cr(CO)3 series the substitution of the β endo hydrogen atom by alkyl groups has shown an increased reactivity towards NaBH4 reduction attributed to a deconjugation of carbonyl group.While in the endo α-substituted series, a decreased reactivity controlled by an enhancement of the activation enthalpy has been observed.The steric origin of this effect and its influence on the position of the transition state are discussed.

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.

Nickel-Catalyzed Domino Heck-Type Reactions Using Methyl Esters as Cross-Coupling Electrophiles

While esters are frequently used as traditional electrophiles in substitution chemistry, their application in cross-coupling chemistry is still in its infancy. This work demonstrates that methyl esters can be used as coupling electrophiles in Ni-catalyzed Heck-type reactions through the challenging cleavage of the C(acyl)?O bond under relatively mild reaction conditions at either 80 or 100 °C. With the σ-NiII intermediate generated from the insertion of acyl NiII species into the tethered C=C bond, carbonyl-retentive products were formed by domino Heck/Suzuki–Miyaura coupling and Heck/reduction pathways when organoboron and mild hydride nucleophiles are used.

Iron-Catalyzed Borrowing Hydrogen β- C(sp3)-Methylation of Alcohols

Herein we report the iron-catalyzed β-C(sp3)-methylation of primary alcohols using methanol as a C1 building block. This borrowing hydrogen approach employs a well-defined bench-stable (cyclopentadienone)iron(0) carbonyl complex as precatalyst (5 mol %) and enables a diverse selection of substituted 2-arylethanols to undergo β-C(sp3)-methylation in good isolated yields (24 examples, 65% average yield).

Manganese catalyzed α-methylation of ketones with methanol as a C1 source

The direct α-methylation of ketones with methanol under hydrogen borrowing conditions using a well-defined manganese PN3P complex as a pre-catalyst was, for the first time, achieved. The reactions typically proceed at 120 °C for 20 h with 3 mol% pre-catalyst loading and in the presence of NaOtBu (50 mol%) as base. The scope of the reaction was extended to the α-methylation of esters.

Design, synthesis and biological evaluation of tetrazole-containing RXRα ligands as anticancer agents

Nuclear receptor RXRα plays an important role in many biological and pathological processes. The nongenomic action of RXRα is implicated in many cancers. K-8008, a non-canonical RXRα ligand derived from sulindac, inhibits the TNFα-activated PI3K/AKT pathway by mediating the interaction between a truncated form of RXRα (tRXRα) and the p85α regulatory subunit of PI3K and exerts potent anticancer activity in animal model. Herein we report our studies of a novel series of K-8008 analogs as potential anticancer agents targeting RXRα. Two compounds 8b and 18a were identified to have slightly stronger binding to RXRα and improved apoptotic activities in breast cancer cells.

B(C6F5)3-Catalyzed Highly Stereoselective Hydrogenation of Unfunctionalized Tetrasubstituted Olefins

A metal-free hydrogenation of unfunctionalized tetrasubstituted olefins were successfully realized using a combination of B(C6F5)3 and Ph2NMe catalyst. The corresponding products were afforded in 58-98% yields with up to >99:1 cis/trans selectivity.