24623-20-9

Basic information

• Product Name: 6-Methyl-1-indanone
• Synonyms: 6-METHYL-1-INDANONE;6-METHYL-INDAN-1-ONE;2,3-DIHYDRO-6-METHYLINDEN-1-ONE;6-METHYL-1-INDANONE,98.0+%(GC);6-Methyl-2,3-dihydro-1H-inden-1-one;2,3-Dihydro-6-methyl-1H-inden-1-one, 2,3-Dihydro-6-methyl-1-oxo-1H-indene;6-Methxy-1- indanone
• CAS NO: 24623-20-9
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.19
• Product Categories: Indanone & Indene;C10;Carbonyl Compounds;Ketones
• Mol File: 24623-20-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 60-62 °C(lit.)
• Boiling Point: 70 °C0.4 mm Hg(lit.)
• Flash Point: 124-126°C/11mm
• Appearance: white to light yellow crystal powder
• Density: 0.9071 (rough estimate)
• Vapor Pressure: 0.00935mmHg at 25°C
• Refractive Index: 1.5580 (estimate)
• Solubility: soluble in Methanol
• BRN: 1448005
• CAS DataBase Reference: 6-Methyl-1-indanone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methyl-1-indanone(24623-20-9)
• EPA Substance Registry System: 6-Methyl-1-indanone(24623-20-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 24623-20-9(Hazardous Substances Data)

Usage

Description

6-Methyl-1-indanone is a substituted indanone, characterized by its white to light yellow crystal powder appearance. It has been synthesized in high quantum yields through the photolysis of α-chloro-2′,5′-dimethylacetophenone and is also formed as one of the photoproducts during the irradiation of 2,5-dimethylphenacyl (DMP) esters. Additionally, it is identified as one of the semivolatile components of lamina cigarette smoke.

Uses

Used in Chemical Synthesis:
6-Methyl-1-indanone is utilized as a starting material for the synthesis of branched alkyl indanes (BINs). Its unique chemical structure makes it a valuable precursor in the creation of various organic compounds, particularly those with potential applications in the chemical and pharmaceutical industries.
Used in Pharmaceutical Industry:
As a key intermediate in the synthesis of certain pharmaceutical compounds, 6-Methyl-1-indanone plays a crucial role in the development of new drugs. Its ability to be modified and functionalized allows for the creation of molecules with specific therapeutic properties.
Used in Research and Development:
Due to its unique photochemical properties and formation as a photoproduct, 6-Methyl-1-indanone is also used in research and development for studying the mechanisms of photochemical reactions and the behavior of semivolatile organic compounds in various environments, including the study of cigarette smoke composition and its effects on health.
Used in Environmental Studies:
6-Methyl-1-indanone's identification as a semivolatile component of lamina cigarette smoke makes it an important compound for environmental studies, particularly in understanding the impact of cigarette smoke on air quality and human health. It can be used to develop methods for monitoring and controlling the emission of harmful substances from cigarette smoke.

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

Upstream product

• 107-94-8 chloropropionic acid 
• 108-88-3 toluene 
• 67-56-1 methanol 
• 50690-11-4 2,5-dimethylphenacyl chloride 
• 378215-21-5 2,5-dimethylphenacyl benzoate 
• 64-17-5 ethanol 
• 71-36-3 butan-1-ol 
• 22422-23-7 3-chloro-1-(3,4-dimethyl-phenyl)-propan-1-one 
• 378215-25-9 2,5-dimethylphenacyl phenylacetate 
• 477218-70-5 2,5-dimethylphenacyl palmitate 

Downstream Products

• 57145-24-1 2,2,6-trimethylindan-1-one 
• 19352-59-1 3,4-dihydro-7-methyl-2(1H)-quinolinone 
• 371756-25-1 7-methyl-1,2,3,4-tetrahydroisoquinolin-1-one 
• 1391033-80-9 3-phenyl-7-methyl-10,10a-dihydroindeno[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 1391033-81-0 3-(p-tolyl)-7-methyl-10,10a-dihydroindeno[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 1391033-64-9 6-methyl-2-tosyloxy-1-indanone 
• 40314-06-5 5-methyl-1H-isoindole-1,3-(2H)-dione 
• 66309-83-9 2,6-dimethylindan-1-one 
• 66703-26-2 2,3,5-trimethyl-1H-indene 

Relevant articles and documents

2,5-Dimethylphenacyl esters: A photoremovable protecting group for carboxylic acidsi

Irradiation of 2,5-dimethylphenacyl (DMP) esters (la-c) in benzene or cyclohexane solutions produces the corresponding free carboxylic acids (2a-c) in high chemical yields, along with 6-methyl-l-indanone (3). In methanol, 2-(methoxymethyl)-5-methylacetophenone (4) is formed as a coproduct. Quantum yields for the photorelease of the DMP group are higher in nonpolar solvents, 0.2, than in methanol, (f> 0.1. The photoreaction is initiated by efficient photoenolization, 01. Three transient intermediates were identified by laser flash photolysis of la, the triplet-state photoenol and the two ground-state photoenols of Z and E configuration. Release of the acids 2a-c occurs predominantly from the E isomer, which has a lifetime of about 2 ms in methanol and 0.5 s in benzene solution. The present data are essential for potential applications of the DMP moiety as a photoremovable protecting group in organic synthesis or biochemistry ( caged compounds ).

Photochemistry of 2-alkoxymethyl-5-methylphenacyl chloride and benzoate

Irradiation of 2-(alkoxymethyl)-5-methyl-α-chloroacetophenones (1a-c) and 2-(methoxymethyl)-5-methylphenacyl benzoate (1d) in dry, nonnucleophilic solvents afforded 3-alkoxy-6-methylindan-1-ones (3a-c) in very high chemical yields. 3-Methylisobenzofuran-1

Photoenolization with α-Chloro Substituents

Irradiation of a methanol solution of 2,5-dimethyl-α-chloropropiophenone (1a) produces 2,6-dimethyl-1-indanone (2a), 2-(methoxymethyl)-5-methylpropiophenone (3a), 2,5-dimethylpropiophenone (4a), and methyl 2-(2,5-dimethylphenyl)propionate (5a).It is proposed that the first two products arise from hydrogen abstraction followed by chlorine loss, the latter two from initial loss of chlorine.Making the chlorine-bearing carbon primary suppresses the formation of the latter two products, while maintaining the carbonyl nearly planar with the ring suppresses all product formation.Other examples are presented.