4-CHLOROBENZYLIDENE PHTHALIDE

Base Information

• Chemical Name: 4-CHLOROBENZYLIDENE PHTHALIDE
• CAS No.: 20526-97-0
• Molecular Formula: C15H9ClO2
• Molecular Weight: 256.688
• Hs Code.: 2932209090
• European Community (EC) Number: 243-862-5
• UNII: F9B1HR45M3
• DSSTox Substance ID: DTXSID00147045
• Nikkaji Number: J280.608H,J830.577C
• Wikidata: Q27277844
• ChEMBL ID: CHEMBL304786
• Mol file: 20526-97-0.mol

Synonyms:3-[(4-chlorophenyl)methylene]phthalide;3-(4-chlorobenzylidene)-2-benzofuran-1(3H)-one;3-(4-Chlorobenzylidene)-2,4-pentanedione;3-(p-Chlorobenzylidene)phthalide;1-Oxo-3-(4-chlor-benzyliden)-phthalan;3-(4-chlorobenzylidene)pentane-2,4-dione;Azelastine impurity E;3-(4-chloro-benzylidene)-3H-isobenzofuran-1-one;3-(p-chlorobenzylidene)-2,4-pentandione;

Chemical Property of 4-CHLOROBENZYLIDENE PHTHALIDE

Chemical Property:

• Vapor Pressure: 6.76E-07mmHg at 25°C
• Melting Point: 153.0 to 158.0 °C
• Boiling Point: 408.9°C at 760 mmHg
• Flash Point: 220.4°C
• PSA: 26.30000
• Density: 1.381g/cm³
• LogP: 4.00850
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly)
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 256.0291072
• Heavy Atom Count: 18
• Complexity: 356

Purity/Quality:

98%, ^*data from raw suppliers

3-(4-Chlorobenzal)phthalide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC3=CC=C(C=C3)Cl)OC2=O
• Isomeric SMILES: C1=CC=C2C(=C1)/C(=C/C3=CC=C(C=C3)Cl)/OC2=O
• Uses: 3-(4-Chlorobenzal)phthalide is stilbene-related benzalphthalide derivative with with potential anti-HIV and leishmanicidal activity. It has anxiolytic effects and maybe useful in the development of a non-benzodiazepinic and non-nit rogenated antianxiety agents. Stilbene-related benzalphthalide derivative with with potential anti-HIV and leishmanicidal activity. It has anxiolytic effects and maybe useful in the development of a non-benzodiazepinic and non-nitrogenated antianxiety agents.An impurity arising in the synthesis of azelastine (A808250).

Technology Process of 4-CHLOROBENZYLIDENE PHTHALIDE

There total 10 articles about 4-CHLOROBENZYLIDENE 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: 85.0%

2-(2-(4-chlorophenyl)ethynyl)benzoic acid methyl ester (118520-71-1) → 3-(p-chlorophenyl)-1H-isochromen-1-one (62827-72-9) + 3-(4-chlorobenzylidene)-2-benzofuran-1(3H)-one (20526-97-0)

Guidance literature:

With trimethylbenzylammonium methanesulfonate; toluene-4-sulfonic acid; at 90 ℃; for 3h; Overall yield = 100 %; regioselective reaction; Microwave irradiation; Green chemistry;

DOI:10.1002/ejoc.201801884

Reference yield: 65.0%

4-chlorophenylacetic Acid (1878-66-6) + phthalic anhydride (85-44-9) → 3-(4-chlorobenzylidene)-2-benzofuran-1(3H)-one (20526-97-0)

Guidance literature:

With sodium acetate; In acetonitrile; at 85 ℃; for 0.333333h; Microwave irradiation;

DOI:10.1080/00397911.2011.622847

Reference yield:

2-((4-chlorophenyl)ethynyl)benzoic acid → 3-(p-chlorophenyl)-1H-isochromen-1-one (62827-72-9) + 3-(4-chlorobenzylidene)-2-benzofuran-1(3H)-one (20526-97-0)

Guidance literature:

With [Rh(bim)(CO)2]BArF; In benzene-d6; at 60 ℃; for 2.13h; regioselective reaction;

DOI:10.1016/j.poly.2013.06.010

upstream raw materials:

4-chlorophenylacetic Acid

phthalic anhydride

o-iodo-methyl-benzoic acid

2-(2-(4-chlorophenyl)ethynyl)benzoic acid methyl ester

Downstream raw materials:

4-(2-carboxyphenethyl)chlorobenzene

2-(4-chlorophenyl)-3-phenyl-1H-inden-1-one

2-p-Chlorphenyl-3-α-naphthyl-indenon

2-p-Chlorphenyl-3,3-dibenzylindanon

Refernces

• 1、 Umeda, Rui,Yoshikawa, Shunya,Yamashita, Kouji,Nishiyama, Yutaka. "Synthesis of isocoumarins: Rhenium complex-catalyzed cyclization of 2-ethynylbenzoic acids". . p. 2172 - 2179. Retrieved 2015/12/12.
• 2、 Man, Bradley Y.-W.,Knuhtsen, Astrid,Page, Michael J.,Messerle, Barbara A.. "Directing the regioselectivity of rhodium(I) catalysed cyclisation of 2-alkynyl benzoic acids". . p. 248 - 252. Retrieved 2013/10/22.