Phthalan

Base Information

• Chemical Name: Phthalan
• CAS No.: 496-14-0
• Molecular Formula: C8H8O
• Molecular Weight: 120.151
• Hs Code.: 29321900
• European Community (EC) Number: 207-815-2
• UNII: 2R6NTQ7Y6G
• DSSTox Substance ID: DTXSID60197920
• Nikkaji Number: J6.090I
• Wikipedia: Phthalane
• Wikidata: Q7188202
• ChEMBL ID: CHEMBL457734
• Mol file: 496-14-0.mol

Synonyms:1,3-dihydro isobenzofuran;1,3-dihydro-2-benzofuran;1,3-dihydroisobenzofuran;phthalan;phthalane

Chemical Property of Phthalan

Chemical Property:

• Appearance/Colour: clear colourless to slightly yellow liquid
• Vapor Pressure: 0.696mmHg at 25°C
• Melting Point: 6oC
• Refractive Index: n20/D 1.546(lit.)
• Boiling Point: 191.999 °C at 760 mmHg
• Flash Point: 63.333 °C
• PSA: 9.23000
• Density: 1.097 g/cm³
• LogP: 1.71680
• Solubility.: Low aqueous solubility.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 120.057514874
• Heavy Atom Count: 9
• Complexity: 88.7

Purity/Quality:

97% ^*data from raw suppliers

Phthalan ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25-3/9/49

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzofuran Derivatives
• Canonical SMILES: C1C2=CC=CC=C2CO1
• General Description: Phthalan, also known as 1,3-dihydroisobenzofuran or isocoumaran, is a heterocyclic compound featuring a fused benzene and furan ring system. It serves as a key structural motif in various chemical reactions and applications, such as the synthesis of dihydroisobenzofuran derivatives, which are utilized in reactions catalyzed by palladium(II) acetate or as water-soluble singlet oxygen probes. The compound's reactivity and utility are influenced by its electron-deficient or electron-rich nature, making it valuable in organic synthesis and photochemical studies.

Technology Process of Phthalan

There total 65 articles about Phthalan 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: 96.0%

o-Xylylene dichloride (612-12-4) → 1,3-dihydroisobenzofuran (496-14-0)

Guidance literature:

With sodium hydroxide; In water; at 100 ℃; for 4h; pH=12;

Reference yield: 95.0%

phthalyl alcohol (612-14-6) → 1,3-dihydroisobenzofuran (496-14-0)

Guidance literature:

With sodium methylate; In carbonic acid dimethyl ester; acetonitrile; for 4h; Inert atmosphere;

DOI:10.1002/cssc.201100755

Reference yield: 92.0%

o-Xylylene dichloride (612-12-4) → 1,3-dihydroisobenzofuran (496-14-0) + phthalyl alcohol (612-14-6) + 2-(chloromethyl)-phenyl methanol (142066-41-9)

Guidance literature:

With sodium hydroxide; In water; at 100 ℃; for 4h; pH=7;

upstream raw materials:

phthalic anhydride

phthalyl alcohol

methanol

2-(Methoxymethyl)benzaldehyde tosylhydrazone

Downstream raw materials:

2-benzofuran-1(3H)-one

[2-(chloromethyl)phenyl]methyl acetate

isochroman-3-one

1-<(2-hydroxymethylphenyl)methyl>cyclohexanol

Refernces

An unexpected addition of acetic acid to ortho-electron-deficient alkynyl-substituted aryl aldehydes catalyzed by palladium(II) acetate

10.1002/adsc.201301170

The research describes an unexpected cyclization reaction of ortho-electron-deficient alkynyl-substituted aryl aldehydes with acetic acid, catalyzed by palladium(II) acetate, resulting in the synthesis of dihydroisobenzofurans in moderate to good yields. The study aimed to understand the role of electron-withdrawing groups on alkynes in this cyclization process and found that these groups are crucial for the reaction to occur. The researchers concluded that the electron-withdrawing groups make the alkyne more electrophilic, facilitating its attack by the hemi-acylal oxygen atom, and render the reaction irreversible, leading to the formation of 5-exo-dig products. The chemicals used in the process include Pd(OAc)2 as the catalyst, 4,4’-dimethoxy-bpy as the ligand, and various substituted 2-alkynylbenzaldehydes as substrates, along with acetic acid and other nucleophiles such as methanol, propionic acid, and benzoic acid.

A New Water-soluble Singlet Oxygen Probe

10.1039/c39820001147

The research aimed to synthesize a new water-soluble singlet oxygen probe, which is crucial for studying the formation and biological implications of singlet oxygen in aqueous media. The researchers synthesized a dihydroisobenzofuran derivative, specifically the potassium salt of (4,7-dihydro-5,6-dimethylisobenzofuran-1,3-diyl)bis(benzene-p-decanoic acid), known as DIBA. This compound was designed to overcome the limitations of previous water-soluble singlet oxygen traps, which had strong absorption in the visible region, complicating kinetic studies. The study concluded that DIBA is a suitable probe for singlet oxygen due to its rapid bleaching upon reaction, and the involvement of superoxide radicals in the bleaching process was indicated by the change in reaction rate in argon-saturated and deuteriated water solutions. Key chemicals used in the synthesis process included hematoporphyrin (HP) as a photosensitizer, and various reagents in the multi-step synthesis scheme such as EtO2C[CH2]2COCI, H2, Pd-C, MeCO2H-HCl, fumaroyl chloride, AlCl3, and KOH-EtOH.