20294-39-7

Basic information

• Product Name: 6-methylindan-5-ol
• Synonyms: 6-methylindan-5-ol;Einecs 243-709-2
• CAS NO: 20294-39-7
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.20168
• EINECS: 243-709-2
• Mol File: 20294-39-7.mol

Chemical Properties

• Boiling Point: 270.3°Cat760mmHg
• Flash Point: 121.5°C
• Appearance: /
• Density: 1.112g/cm³
• Vapor Pressure: 0.00415mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 6-methylindan-5-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methylindan-5-ol(20294-39-7)
• EPA Substance Registry System: 6-methylindan-5-ol(20294-39-7)

Safety Data

• Hazardous Substances Data: 20294-39-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 2159, 1985 DOI: 10.1016/S0040-4039(00)98950-0Journal of the American Chemical Society, 107, p. 1060, 1985 DOI: 10.1021/ja00290a053

InChI:InChI=1/C10H12O/c1-7-5-8-3-2-4-9(8)6-10(7)11/h5-6,11H,2-4H2,1H3

Upstream product

• 1685-78-5 5-Methoxy-6-methyl-indan 
• 2396-63-6 hepta-1,6-diyne 
• 82472-15-9 6-Hydroxymethyl-5-indanol 
• 1321908-57-9 2-methylenenona-3,8-diyn-1-ol 
• 344308-94-7 3-(4-Methoxy-3-methyl-phenyl)-propionyl chloride 
• 1685-77-4 6-Methoxy-5-methyl-indan-1-on 
• 7647-01-0 hydrogenchloride 
• 67199-56-8 5-methoxy-6-methyl-1-indanone 
• 108-88-3 toluene 
• 95615-32-0 6-Methoxy-6-methyl-1,2,3,6-tetrahydro-inden-5-one 

Downstream Products

• 1321908-71-7 6-methyl-2,3-dihydro-1H-inden-5-yl-3,5-dinitrobenzoate 

Relevant articles and documents

Molecular complexity from aromatics: A novel, stereoselective route to tricyclo[5.2.2.01,5]undecenones, tricyclo[6.2.2.01,6] dodecenones, and [n.3.3]propellanes

(Chemical Equation Presented) A general stereoselective route to functionalized and substituted tricyclo [5.2.2.01,5]undecenones, tricyclo-[6.2.2.01,6]dodecenones, and [3.3.3]- and [4.3.3]propellanes from simple aromatic precursors is reported. The methodology involves generation and cycloaddition of annulated cyclohexa-2,4-dienones with various acrylates followed by manipulation of the resulting tricyclic adducts, leading to functionalized tricyclo-[5.2.2.01,5]undecenones and tricyclo[6.2.2.01,6]dodecenones endowed with a β,γ-enone chromophore. Photochemical reaction of the tricyclic chromophoric systems followed by reductive cleavage provided an efficient entry into propellanes.

Gold catalysis: Domino reaction of En-diynes to highly substituted phenols

By Sonogashira coupling of 1,7-heptadiynes and 1,8-octadiynes with 2-iodoallyl alcohols, various substrates that bear a 2-alkynylallyl alcohol moiety tethered to an additional alkyne were prepared in one step. Subjection to nitrogen acyclic carbene (NAC)/gold(I) catalysts delivered highly substituted phenols in an efficient domino reaction. Furan derivatives were formed as intermediates; this was proven by in situ NMR spectroscopy. The uncommon substitution pattern of these furans opens the way for a selective formation of phenols that contain the hydroxyl group in the meta position to the ring junction, which previously was not possible by gold-catalyzed furan-yne cyclization. Furthermore, interesting mechanistic insights were obtained by products derived from secondary allyl alcohols. In this case, in addition to the phenolic compounds, a ketone is formed by 1,2-alkyl shift.

Synthesis and Thermolysis of Enediynyl Ethyl Ethers as Precursors of Enyne - Ketenes

Enediynyl ethyl ethers 14/17 were synthesized by using the Pd(PPh3)4-catalyzed cross-coupling factions between enynyl iodides 13/16 and (2-ethoxyethynyl)zinc chloride. Thermolysis of these enediynyl ethyl ethers in refluxing chlorobenzene (132°C) promoted a retro-ene reaction to produce enyne - ketenes, which underwent the Moore cyclization reactions to form the biradicals having a phenyl radical center and a phenoxy radical center. The presence of two radical centers in he same molecule simultaneously provided many opportunities for intramolecular decay through disproportionate, radical - radical combination, and the formation of o-quinone methide.

Alkylations of Tetracarbonyl(phosphine)chromium and Pentacarbonylchromium Carbene Complexes and Their Reactions with Selected Acetylenes

The thermodynamic acidity of (methylmethoxymethylene)tetracarbonyl(tri-n-butylphosphine)chromium (1b) was found to be 6 orders of magnitude less than that of (methylmethoxymethylene)pentacarbonylchromium (1a).The anion 2b is generated from 1b by deprotona

SYNTHESIS OF PHENOLS FROM METAL-CARBYNES AND DIYNES

Metal-carbynes RCM(CO)4Br with diacetylenes give specific phenols in good yield.The reactions take only a few minutes at or below room temperature.

Synthesis and antianxiety activity of (ω-piperazinylalkoxy)indan derivatives

A series of (ω-piperazinylalkoxyl)indan derivatives has been synthesized and screened for potential antianxiety activities. The effect of structural modification of these molecules on activities has been systematically examined. Antianxiety activity was displayed by 5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (2), 5-[3-(4-[4-fluorophenyl)-1-piperazinyl]propoxy]indan (8), 6-fluoro-5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (33), and 6-methyl-5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (42), as determined in antifighting and anti-morphine tests. These derivatives in antianxiety tests were equipotent or more potent than chloridazepoxide with less muscle-relaxant effect. They also showed weak neuroleptic-like action.