6-Fluoro-4-methylindan-1-one

Base Information

• Chemical Name: 6-Fluoro-4-methylindan-1-one
• CAS No.: 174603-42-0
• Molecular Formula: C10H9FO
• Molecular Weight: 164.1763
• European Community (EC) Number: 808-750-8
• DSSTox Substance ID: DTXSID20455715
• Wikidata: Q82277826
• Mol file: 174603-42-0.mol

Synonyms:174603-42-0;6-FLUORO-4-METHYLINDAN-1-ONE;6-Fluoro-4-methyl-2,3-dihydro-1H-inden-1-one;6-fluoro-4-methyl-2,3-dihydroinden-1-one;1H-Inden-1-one, 6-fluoro-2,3-dihydro-4-methyl-;SCHEMBL8366049;DTXSID20455715;XFAXYSVQFDBFSK-UHFFFAOYSA-N;AM9203;MFCD09038175;AKOS011405160;MB06887;TS-02191;FT-0659130;6-fluoranyl-4-methyl-2,3-dihydroinden-1-one;N11084;EN300-7801421;A811668;A1-12435

Chemical Property of 6-Fluoro-4-methylindan-1-one

Chemical Property:

• Boiling Point: 271.305 °C at 760 mmHg
• Flash Point: 102.783 °C
• PSA: 17.07000
• Density: 1.212 g/cm³
• LogP: 2.26300
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 164.063743068
• Heavy Atom Count: 12
• Complexity: 202

Purity/Quality:

98% ^*data from raw suppliers

6-Fluoro-4-methylindan-1-one 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC2=C1CCC2=O)F

Technology Process of 6-Fluoro-4-methylindan-1-one

There total 7 articles about 6-Fluoro-4-methylindan-1-one 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: 70.0%

3-(4-fluoro-2-methylphenyl)propionic acid (166251-34-9) → 6-fluoro-4-methyl-1-indanone (174603-42-0)

Guidance literature:

3-(4-fluoro-2-methylphenyl)propionic acid; With oxalyl dichloride; In dichloromethane; at 20 ℃; for 16h;

With aluminum (III) chloride; In dichloromethane; at 0 - 50 ℃; for 19h;

Reference yield:

2-Bromo-5-fluorotoluene (452-63-1) → 6-fluoro-4-methyl-1-indanone (174603-42-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / triethylamine; palladium(II) acetate; tri-o-tolylphosphine / acetonitrile / 12 h / 110 °C

2: 33.7 g / H₂ / platinum oxide hydrate / aq. ethanol

3: 91 percent / aq. NaOH / ethanol / 18 h / 20 °C

4: oxalyl chloride / CH₂Cl₂ / 18 h / 20 °C

5: 11.9 g / aluminum chloride / CH₂Cl₂ / 2.5 h / Heating

With sodium hydroxide; aluminium trichloride; oxalyl dichloride; hydrogen; palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; platinum(IV) oxide; In ethanol; dichloromethane; acetonitrile; 1: Heck reaction / 5: Friedel-Crafts reaction;

DOI:10.1021/jm020068k

Reference yield:

(E)-ethyl 3-(4-fluoro-2-methylphenyl)acrylate (500102-62-5) → 6-fluoro-4-methyl-1-indanone (174603-42-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 33.7 g / H₂ / platinum oxide hydrate / aq. ethanol

2: 91 percent / aq. NaOH / ethanol / 18 h / 20 °C

3: oxalyl chloride / CH₂Cl₂ / 18 h / 20 °C

4: 11.9 g / aluminum chloride / CH₂Cl₂ / 2.5 h / Heating

With sodium hydroxide; aluminium trichloride; oxalyl dichloride; hydrogen; platinum(IV) oxide; In ethanol; dichloromethane; 4: Friedel-Crafts reaction;

DOI:10.1021/jm020068k

upstream raw materials:

2-Bromo-5-fluorotoluene

3-(4-fluoro-2-methylphenyl)propionic acid

(E)-ethyl 3-(4-fluoro-2-methylphenyl)acrylate

ethyl 3-(4-fluoro-2-methylphenyl)propionate

Refernces

• 1、 Musso, David L.,Orr, G. Faye,Cochran, Felicia R.,Kelley, James L.,Selph, Jeffrey L.,Rigdon, Greg C.,Cooper, Barrett R.,Jones, Michael L.. "Indanylidenes. 2. Design and synthesis of (E)-2-(4-chloro-6-fluoro-1-indanylidene)-N-methylacetamide, a potent antiinflammatory and analgesic agent without centrally acting muscle relaxant activity". . p. 409 - 416. Retrieved 2007/10/03.