5-Fluoroisobenzofuran-1(3H)-one

Base Information

• Chemical Name: 5-Fluoroisobenzofuran-1(3H)-one
• CAS No.: 700-85-6
• Molecular Formula: C8H5FO2
• Molecular Weight: 152.125
• Hs Code.: 2932209090
• ChEMBL ID: CHEMBL226398
• DSSTox Substance ID: DTXSID60548958
• Nikkaji Number: J3.320.040D
• Wikidata: Q82427819
• Mol file: 700-85-6.mol

Synonyms:5-Fluoroisobenzofuran-1(3H)-one;700-85-6;5-Fluoro-1(3h)-isobenzofuranone;5-FLUORO-3H-2-BENZOFURAN-1-ONE;5-fluoro-1,3-dihydro-2-benzofuran-1-one;CHEMBL226398;MFCD09842448;1(3H)-ISOBENZOFURANONE,5-FLUORO-;5-fluorophthalide;5-Fluoro-Phthalide;SCHEMBL365201;DTXSID60548958;KKDJJBAMSYLYQS-UHFFFAOYSA-N;5-Fluoro-2-benzofuran-1(3H)-one;BDBM50370989;AKOS005215807;AM807120;DS-18650;SY242224;CS-0043979;EN300-3224863;A836763;Z1198234543;5-fluoro-3H-isobenzofuran-1-one

Chemical Property of 5-Fluoroisobenzofuran-1(3H)-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 118-119 °C
• Boiling Point: 322.686oC at 760 mmHg
• Flash Point: 144.107oC
• PSA: 26.30000
• Density: 1.379g/cm3
• LogP: 1.49610
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 152.02735756
• Heavy Atom Count: 11
• Complexity: 181

Purity/Quality:

99%, ^*data from raw suppliers

5-Fluoro-1(3h)-isobenzofuranone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C=CC(=C2)F)C(=O)O1

Technology Process of 5-Fluoroisobenzofuran-1(3H)-one

There total 3 articles about 5-Fluoroisobenzofuran-1(3H)-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: 57.0%

copper(l) cyanide + 2-bromo-5-fluorobenzyl alcohol (202865-66-5) → 5-fluoroisobenzofuran-1(3H)-one (700-85-6)

Guidance literature:

In N,N-dimethyl-formamide; at 100 - 180 ℃; for 21h; Inert atmosphere;

Reference yield:

4-fluoro-2-(hydroxymethyl)benzyl alcohol (62558-08-1) → 6-fluoroisobenzofuran-1(3H)-one (23932-84-5) + 5-fluoroisobenzofuran-1(3H)-one (700-85-6)

Guidance literature:

With [(η⁵-C₅Me₅)Ir(6,6'-dihydroxy-2,2'-bipyridine)(H₂O)]OTf₂; In water; for 6h; Overall yield = 94 %; Inert atmosphere; Reflux; Green chemistry;

DOI:10.1002/cctc.201300717

Reference yield:

4-fluorophthalic anhydride (319-03-9) → 6-fluoroisobenzofuran-1(3H)-one (23932-84-5) + 5-fluoroisobenzofuran-1(3H)-one (700-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: 10% Pt/activated carbon; oxygen / water / 12 h / 80 °C / 760.05 Torr / Sealed tube

With lithium aluminium tetrahydride; 10% Pt/activated carbon; oxygen; In tetrahydrofuran; water;

DOI:10.1055/s-0037-1611917

upstream raw materials:

4-fluoro-2-(hydroxymethyl)benzyl alcohol

4-fluorophthalic anhydride

2-bromo-5-fluorobenzyl alcohol

Downstream raw materials:

2-<(4-Fluorophenyl)oxymethyl>-4-fluorobenzoic acid

5-fluoro-3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile

2-(4-chlorophenylthiomethyl)-4-fluorobenzoic acid

4-(4-chlorophenylthio)-2-(4-chlorophenylthiomethyl)benzoic acid