3-[(4-methoxyphenyl)methylene]phthalide

Base Information

• Chemical Name: 3-[(4-methoxyphenyl)methylene]phthalide
• CAS No.: 4767-61-7
• Molecular Formula: C16H12O3
• Molecular Weight: 252.269
• European Community (EC) Number: 225-308-4
• NSC Number: 61720
• Nikkaji Number: J830.570F,J262.443E
• ChEMBL ID: CHEMBL67100
• Mol file: 4767-61-7.mol

Synonyms:3-[(4-methoxyphenyl)methylidene]isobenzofuran-1-one;3-(4-Methoxybenzylidene)-2-benzofuran-1(3H)-one;1(3H)-Isobenzofuranone, 3-[(4-methoxyphenyl)methylene]-;NSC61720;AC1L3ZKU;

Chemical Property of 3-[(4-methoxyphenyl)methylene]phthalide

Chemical Property:

• Vapor Pressure: 2.15E-07mmHg at 25°C
• Refractive Index: 1.658
• Boiling Point: 423.9 °C at 760 mmHg
• Flash Point: 180.4 °C
• PSA: 35.53000
• Density: 1.274 g/cm³
• LogP: 3.36370
• Solubility.: Acetone, Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 252.078644241
• Heavy Atom Count: 19
• Complexity: 366

Purity/Quality:

99%, ^*data from raw suppliers

p-Anisylidenephthalide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=C2C3=CC=CC=C3C(=O)O2
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C\2/C3=CC=CC=C3C(=O)O2
• Uses: Potential antianxiety agent

Technology Process of 3-[(4-methoxyphenyl)methylene]phthalide

There total 8 articles about 3-[(4-methoxyphenyl)methylene]phthalide 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: 84.0%

2-(4-methoxyphenylethynyl)benzaldehyde (176910-67-1) → 3-(4-methoxybenzylidene)phthalide (4767-61-7) + 3-(4-methoxyphenyl)-1H-isochromen-1-one (29910-92-7)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 0 - 90 ℃; for 16h; regioselective reaction;

DOI:10.1016/j.tetlet.2010.09.023

Reference yield: 66.0%

4-Methoxyphenylacetic acid (104-01-8) + phthalic anhydride (85-44-9) → 3-(4-methoxybenzylidene)phthalide (4767-61-7)

Guidance literature:

With sodium acetate; at 240 ℃; for 4h; Dean-Stark;

DOI:10.1016/j.ejmech.2014.08.016

Reference yield: 62.0%

2-Iodobenzoic acid (88-67-5) + copper(I) 4-methoxyphenylacetylenide (48121-13-7) → 3-(4-methoxybenzylidene)phthalide (4767-61-7)

Guidance literature:

In N,N-dimethyl-formamide; at 140 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jafc.1c05792

upstream raw materials:

4-Methoxyphenylacetic acid

phthalic anhydride

4-methoxyphenyl acetate

2-(4-methoxyphenylethynyl)benzaldehyde

Downstream raw materials:

3-(4-(4-methoxybenzyl)-1-oxophthalazin-2(1H)-yl)-N-(4-(N-(pyrimidin-2-yl)sulfamoyl)phenyl)propanamide

3-(4-(4-methoxybenzyl)-1-oxophthalazin-2(1H)-yl)-N-(4-sulfamoylphenyl)propanamide

2-(4-(4-methoxybenzyl)-1-oxophthalazin-2(1H)-yl)-N-(4-(N-(pyrimidin-2-yl)sulfamoyl)phenyl)acetamide

2-(4-(4-methoxybenzyl)-1-oxophthalazin-2(1H)-yl)-N-(4-sulfamoylphenyl)acetamide

Refernces

• 1、 Wang, Yan-Hua,Qiu, Guanyinsheng,Zhou, Hongwei,Xie, Wenlin,Liu, Jin-Biao. "Regioselective cyclization of 2-alkynylbenzoic acid in water for the synthesis of isocoumarin". supporting information. p. 3850 - 3855. Retrieved 2019/06/17.
• 2、 Ibrahim, Hany S.,Eldehna, Wagdy M.,Abdel-Aziz, Hatem A.,Elaasser, Mahmoud M.,Abdel-Aziz, Marwa M.. "Improvement of antibacterial activity of some sulfa drugs through linkage to certain phthalazin-1(2H)-one scaffolds". . p. 480 - 486. Retrieved 2014/09/03.