1-Methylindan

Base Information

• Chemical Name: 1-Methylindan
• CAS No.: 767-58-8
• Molecular Formula: C10H12
• Molecular Weight: 132.205
• European Community (EC) Number: 212-184-1
• NSC Number: 38858
• UNII: 1U9UL1200M
• DSSTox Substance ID: DTXSID80862406
• Nikkaji Number: J130.639A
• Wikidata: Q27252897
• Mol file: 767-58-8.mol

Synonyms:1-Methylindan;767-58-8;1-methyl-2,3-dihydro-1H-indene;2,3-Dihydro-1-methyl-1H-indene;1-Methylindane;Indan, 1-methyl-;Methylindane;1-Methyl-2,3-dihydroindene;METHYLINDAN;1H-Indene, 2,3-dihydro-1-methyl-;27133-93-3;UNII-59G65VPV4O;1H-Indene, 2,3-dihydromethyl-;EINECS 212-184-1;NSC 38858;NSC-38858;2,3-DIHYDRO-1-METHYLINDENE;UNII-1U9UL1200M;59G65VPV4O;1H-Indene,3-dihydro-1-methyl-;DTXSID80862406;1U9UL1200M;NSC38858;1-METHYLINDANE, (+/-)-;MFCD11846372;AS-60060;Q27252897

Chemical Property of 1-Methylindan

Chemical Property:

• Vapor Pressure: 0.649mmHg at 25°C
• Refractive Index: 1.5266
• Boiling Point: 193.4°C at 760 mmHg
• Flash Point: 61.3°C
• PSA: 0.00000
• Density: 0.954g/cm³
• LogP: 2.73630
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 132.093900383
• Heavy Atom Count: 10
• Complexity: 117

Purity/Quality:

99% ^*data from raw suppliers

1-Methylindan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2=CC=CC=C12
• Uses: 1-Methylindan is a component of fuels that is synthesized from 1-indanone (I499900). 1-Indanone is an oxidation product of Indan, a component of fuels, solvents, and varnishes. 1-Indanone is also a metabolite of Thalidomide that has been shown to inhibit the attachment of tumor cells to concanavalin A coated plastic surfaces.

Technology Process of 1-Methylindan

There total 102 articles about 1-Methylindan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-Methylindene (767-60-2) → 1-methylindane (767-58-8)

Guidance literature:

With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 1,3-bis((R)-1-(naphthalen-1-yl)ethyl)-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate; potassium tert-butylate; hydrogen; In hexane; at 25 ℃; for 16h; under 7500.75 Torr; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Autoclave;

DOI:10.1016/j.tet.2012.03.109

Reference yield: 90.0%

1-bromo-2-(but-3-enyl)benzene (71813-50-8) → 1-methylindane (767-58-8) + 4-Phenylbut-1-ene (768-56-9)

Guidance literature:

With 2-H-1,3-di-tert-butyl-1,3,2-diazaphosphorinane; 2,2'-azobis(isobutyronitrile); In toluene; at 90 ℃; for 8h; chemoselective reaction;

DOI:10.1039/d0sc01352h

Reference yield: 89.0%

1-methyleneindane (1194-56-5) → 1-methylindane (767-58-8)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; at 45 ℃; for 18h; under 3040.2 Torr;

DOI:10.1021/ja300503k

upstream raw materials:

3-Methylindene

3-methylindanone

tetralin

cis-1,2-divinylocyclohexane

Downstream raw materials:

naphthalene

inden-1-one

Refernces

• 1、 Holman, R. W.,Rozeboom, M. D.,Gross, M. L.,Warner, C. D.. "MASS SPECTROMETRY FOR INVESTIGATIONS OF GAS-PHASE RADICAL CATION CHEMISTRY. THE TWO STEP CYCLOADDITION OF THE BENZENE RADICAL CATION AND 1,3-BUTADIENE". . p. 6235 - 6244. Retrieved 1986.
• 2、 Ross, Gerald A.,Koppang, Miles D.,Bartak, Duane E.,Woolsey, Neil F.. "Cyclization of o-(3-Butenyl)bromobenzene via the Aryllithium Derivative". . p. 6742 - 6743. Retrieved 1985.
• 3、 Guyon, Hélène,Castanet, Anne-Sophie,Boussonnière, Anne. "Computational Insight into 1,2-Diamine, -Diether, and -Amino Ether Chiral Ligand-Mediated Carbolithiation: A Case of Enantioinduction Reversal". . p. 8933 - 8943. Retrieved 2020/08/28.
• 4、 Wu, Zhenghan,Si, Tengda,Xu, Guangqing,Xu, Bin,Tang, Wenjun. "Ligand-free nickel-catalyzed Kumada couplings of aryl bromides with tert-butyl Grignard reagents". supporting information. p. 597 - 600. Retrieved 2019/01/05.