3-(2-Fluorophenyl)-3,4-dihydroisocoumarin

Base Information

• Chemical Name: 3-(2-Fluorophenyl)-3,4-dihydroisocoumarin
• CAS No.: 95217-42-8
• Molecular Formula: C15H11 F O2
• Molecular Weight: 0
• DSSTox Substance ID: DTXSID40540910
• Mol file: 95217-42-8.mol

Synonyms:95217-42-8;3-(2-Fluorophenyl)isochroman-1-one;3-(2-Fluorophenyl)-3,4-dihydro-1H-2-benzopyran-1-one;3-(2-FLUOROPHENYL)-3,4-DIHYDROISOCOUMARIN;SCHEMBL4976861;DTXSID40540910

Chemical Property of 3-(2-Fluorophenyl)-3,4-dihydroisocoumarin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.587
• Boiling Point: 380.979°C at 760 mmHg
• Flash Point: 177.899°C
• PSA: 26.30000
• Density: 1.26g/cm³
• LogP: 3.27990
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 242.07430775
• Heavy Atom Count: 18
• Complexity: 318

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(=O)C2=CC=CC=C21)C3=CC=CC=C3F

Technology Process of 3-(2-Fluorophenyl)-3,4-dihydroisocoumarin

There total 5 articles about 3-(2-Fluorophenyl)-3,4-dihydroisocoumarin 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: 77.0%

o-(chloromethyl)benzoic acid methyl ester (34040-62-5) + 2-Fluorobenzaldehyde (446-52-6) → 3-(o-fluorophenyl)-3,4-dihydroisocoumarin (95217-42-8)

Guidance literature:

With N¹,N¹,N¹²,N¹²-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Glovebox; Inert atmosphere;

DOI:10.1021/acs.joc.0c02374

Reference yield:

ortho-methylbenzoic acid (118-90-1) → 3-(o-fluorophenyl)-3,4-dihydroisocoumarin (95217-42-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / thionyl chloride / 18 h / Ambient temperature

2: 100 percent / CH₂Cl₂ / 0.5 h / 0 °C

3: 92 percent / thionyl chloride / 1 h

4: 1.) n-BuLi / 1.) ethyl ether, 0 deg C, 1 h, 2.) RT, overnight

With n-butyllithium; thionyl chloride; In dichloromethane;

DOI:10.1021/jo00208a020

Reference yield:

ortho-toluoyl chloride (933-88-0) → 3-(o-fluorophenyl)-3,4-dihydroisocoumarin (95217-42-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / CH₂Cl₂ / 0.5 h / 0 °C

2: 92 percent / thionyl chloride / 1 h

3: 1.) n-BuLi / 1.) ethyl ether, 0 deg C, 1 h, 2.) RT, overnight

With n-butyllithium; thionyl chloride; In dichloromethane;

DOI:10.1021/jo00208a020

upstream raw materials:

2-Fluorobenzaldehyde

4,5-dihydro-4,4-dimethyl-2-(2-methylphenyl)-2-oxazoline

ortho-methylbenzoic acid

ortho-toluoyl chloride

Refernces

• 1、 Fu,Unruh,Miller,et al.. "Synthesis of 3-aryl-3,4-dihydroisocoumarins". . p. 1259 - 1261. Retrieved 2007/10/02.