6-Hydroxyphthalide

Base Information

• Chemical Name: 6-Hydroxyphthalide
• CAS No.: 55104-32-0
• Molecular Formula: C8H6O3
• Molecular Weight: 150.134
• European Community (EC) Number: 866-523-9
• DSSTox Substance ID: DTXSID90493826
• Wikidata: Q82340793
• Mol file: 55104-32-0.mol

Synonyms:6-Hydroxyphthalide;55104-32-0;6-hydroxy-1(3H)-Isobenzofuranone;6-hydroxy-1,3-dihydro-2-benzofuran-1-one;6-HYDROXY-3H-2-BENZOFURAN-1-ONE;1(3H)-Isobenzofuranone, 6-hydroxy-;SCHEMBL6585556;SCHEMBL7593240;DTXSID90493826;HWIZGBVJDMPJRO-UHFFFAOYSA-N;6-hydroxyisobenzofuran-1(3H)-one;6-Hydroxy-3H-isobenzofuran-1-one;6-Hydroxy-2-benzofuran-1(3H)-one;MFCD08693507;AKOS000278063;AM20080854;CS-0246132;FT-0767661;EN300-317828;Z1198181162

Chemical Property of 6-Hydroxyphthalide

Chemical Property:

• Melting Point: 200.5-201.2 °C
• Boiling Point: 424.2±45.0 °C(Predicted)
• PKA: 9.45±0.20(Predicted)
• PSA: 46.53000
• Density: 1.436±0.06 g/cm3(Predicted)
• LogP: 1.06260
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 150.031694049
• Heavy Atom Count: 11
• Complexity: 178

Purity/Quality:

99% ^*data from raw suppliers

6-hydroxy-1,3-dihydro-2-benzofuran-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 6-Hydroxyphthalide

There total 6 articles about 6-Hydroxyphthalide 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: 92.0%

6-methoxyphthalide (4741-63-3) → 6-hydroxy isobenzofuran-1(3H)-one (55104-32-0)

Guidance literature:

With dichloromethane; boron tribromide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.molstruc.2013.12.059

Reference yield: 79.0%

6-bromophthalide (19477-73-7) → 6-hydroxy isobenzofuran-1(3H)-one (55104-32-0)

Guidance literature:

With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br₂Ni*3H₂O; water; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile; at 20 ℃; for 36h; Glovebox; Irradiation; Inert atmosphere;

DOI:10.1002/anie.201710698

Reference yield: 65.0%

6-aminophthalide (57319-65-0) → 6-hydroxy isobenzofuran-1(3H)-one (55104-32-0)

Guidance literature:

With sulfuric acid; sodium nitrite; In water; at 125 ℃; for 0.0833333h;

DOI:10.1016/j.bmc.2016.09.050

upstream raw materials:

6-aminophthalide

6-methoxyphthalide

6-nitrophthalide

6-bromophthalide

Downstream raw materials:

6-((4-chlorobenzyl)oxy)isobenzofuran-1(3H)-one

C₁₅H₁₁BrO₃

6-((4-fluorobenzyl)oxy)isobenzofuran-1(3H)-one

6-((4-(trifluoromethyl)benzyl)oxy)isobenzofuran-1(3H)-one

Refernces

• 1、 Rodrigues, Michelle Peixoto,Tomaz, Deborah Campos,?ngelo de Souza, Luciana,Onofre, Thiago Souza,Aquiles de Menezes, Wemerson,Almeida-Silva, Juliana,Suarez-Fontes, Ana Márcia,Rogéria de Almeida, Márcia,Manoel da Silva, Adalberto,Bressan, Gustavo Costa,Vannier-Santos, Marcos André,Rangel Fietto, Juliana Lopes,Teixeira, Róbson Ricardo. "Synthesis of cinnamic acid derivatives and leishmanicidal activity against Leishmania braziliensis". . . Retrieved 2019/09/30.
• 2、 Wang, Zhimin,Wu, Jiajia,Yang, Xuelian,Cai, Pei,Liu, Qiaohong,Wang, Kelvin D.G.,Kong, Lingyi,Wang, Xiaobing. "Neuroprotective effects of benzyloxy substituted small molecule monoamine oxidase B inhibitors in Parkinson's disease". supporting information. p. 5929 - 5940. Retrieved 2016/11/09.