3(2H)-Benzofuranone, 6,7-dihydroxy-

Base Information

• Chemical Name: 3(2H)-Benzofuranone, 6,7-dihydroxy-
• CAS No.: 6272-27-1
• Molecular Formula: C8H6 O4
• Molecular Weight: 166.133
• European Community (EC) Number: 228-459-4
• NSC Number: 37408
• UNII: YK1BM25U2J
• DSSTox Substance ID: DTXSID8064191
• Nikkaji Number: J211.509C
• Wikidata: Q81991326
• ChEMBL ID: CHEMBL1728276
• Mol file: 6272-27-1.mol

Synonyms:6272-27-1;6,7-Dihydroxy-benzofuran-3-one;3(2H)-Benzofuranone, 6,7-dihydroxy-;6,7-Dihydroxy-3-coumaranone;6,7-dihydroxybenzofuran-3(2H)-one;6,7-Dihydroxycoumeranone;6,7-Dihydroxycoumaranon;6,7-dihydroxy-1-benzofuran-3-one;6,7-dihydroxy-3(2H)-benzofuranone;YK1BM25U2J;6,7-Dihydroxy-1-benzofuran-3(2H)-one;MLS002608035;CHEMBL1728276;6,7-dihydroxy-2,3-dihydro-1-benzofuran-3-one;EINECS 228-459-4;6,7-Dihydroxy-2H-benzofuran-3-one;MFCD01096462;NSC 37408;NSC-37408;NSC37408;UNII-YK1BM25U2J;Coumaran-6,7-diol-3-one;Oprea1_650259;SCHEMBL6611223;DTXSID8064191;HMS3080B09;3(2H)-Benzofuranone,7-dihydroxy-;BBL012837;BDBM50189336;STK788053;AKOS000266979;AC-14991;SMR001366147;VS-03547;6,7-Dihydroxy-1-benzofuran-3(2H)-one #;CS-0071578;FT-0636058;D83569;EN300-236053;F3139-2620

Chemical Property of 3(2H)-Benzofuranone, 6,7-dihydroxy-

Chemical Property:

• Vapor Pressure: 4.08E-08mmHg at 25°C
• Boiling Point: 433.3°C at 760 mmHg
• Flash Point: 189.1°C
• PSA: 66.76000
• Density: 1.614g/cm³
• LogP: 0.67290
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 166.02660867
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

99%, ^*data from raw suppliers

6,7-Dihydroxy-benzofuran-3-one 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)C2=C(O1)C(=C(C=C2)O)O
• Uses: 6,7-Dihydroxy-benzofuran-3-one is used as a reactant in the preparation of silica sulfonic acid reusable catalyst for α-monobromination of carbonyl compounds using N-bromosuccinimide.

Technology Process of 3(2H)-Benzofuranone, 6,7-dihydroxy-

There total 5 articles about 3(2H)-Benzofuranone, 6,7-dihydroxy- 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%

ω-chloro-2,3,4-trihydroxyacetophenone (17345-68-5) → 6,7-dihydroxybenzofuran-3[2H]-one (6272-27-1)

Guidance literature:

With sodium acetate; In ethanol; for 6h; Heating;

DOI:10.1271/bbb.68.2183

Reference yield:

chloroacetonitrile (107-14-2) + 2-hydroxyresorcinol (87-66-1) → 6,7-dihydroxybenzofuran-3[2H]-one (6272-27-1)

Guidance literature:

chloroacetonitrile; 2-hydroxyresorcinol; With hydrogenchloride; zinc(II) chloride; In diethyl ether; at 20 ℃; for 24h; Inert atmosphere;

In water; for 1h; Reflux;

With sodium acetate; In ethanol; Reflux;

DOI:10.2174/1570180815666180712150600

Reference yield:

2-hydroxyresorcinol (87-66-1) → 6,7-dihydroxybenzofuran-3[2H]-one (6272-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / BF₃ diethyl etherate / 3 h / 65 °C

2: 85 percent / sodium acetate / ethanol / 6 h / Heating

With boron trifluoride diethyl etherate; sodium acetate; In ethanol; 1: Friedel-Crafts reaction;

DOI:10.1271/bbb.68.2183

upstream raw materials:

ω-chloro-2,3,4-trihydroxyacetophenone

2-hydroxyresorcinol

chloroacetonitrile

Downstream raw materials:

2-(2-chloro-benzylidene)-6,7-dihydroxy-benzofuran-3-one

6,7-dihydroxy-2-(3-nitro-benzylidene)-benzofuran-3-one

2-[(Z)-benzylidene-6,7-dihydroxy-benzofuran-3-one

6,7-dihydroxy-2-(2-nitro-benzylidene)-benzofuran-3-one

Refernces

• 1、 Gupta, Anjali,Priya, Nivedita,Jalal, Sarah,Singh, Prabhjot,Chand, Karam,Raj, Hanumantharao G.,Parmar, Virinder S.,DePass, Anthony L.,Sharma, Sunil K.. "Specificity of Calreticulin Transacetylase to acetoxy derivatives of benzofurans: Effect on the activation of platelet Nitric Oxide Synthase". experimental part. p. 1180 - 1185. Retrieved 2011/11/06.
• 2、 Thomas, Michael G.,Lawson, Chris,Allanson, Nigel M.,Leslie, Bruce W.,Bottomley, Joanna R.,McBride, Andrew,Olusanya, Oyinkan A.. "A series of 2(Z)-2-benzylidene-6,7-dihydroxybenzofuran-3[2H]-ones as inhibitors of chorismate synthase". . p. 423 - 426. Retrieved 2007/10/03.