Ethyl 5-hydroxy-2-methyl-1-benzofuran-3-carboxylate

Base Information

• Chemical Name: Ethyl 5-hydroxy-2-methyl-1-benzofuran-3-carboxylate
• CAS No.: 7287-40-3
• Molecular Formula: C12H12 O4
• Molecular Weight: 220.225
• Hs Code.: 2932999099
• European Community (EC) Number: 230-713-4
• NSC Number: 42354
• UNII: 7ZX8M4JY4M
• DSSTox Substance ID: DTXSID10223167
• Nikkaji Number: J212.283I
• Wikidata: Q83101570
• ChEMBL ID: CHEMBL473809
• Mol file: 7287-40-3.mol

Synonyms:7287-40-3;ethyl 5-hydroxy-2-methyl-1-benzofuran-3-carboxylate;ethyl 5-hydroxy-2-methylbenzofuran-3-carboxylate;Ethyl 5-hydroxy-2-methyl-3-benzofurancarboxylate;7ZX8M4JY4M;MLS000530169;EINECS 230-713-4;MFCD00023001;NSC-42354;5-Hydroxy-2-methyl-benzofuran-3-carboxylic acid ethyl ester;SMR000135146;2-methyl-3-carbethoxy-5-hydroxybenzofuran;5-hydroxy-2-methyl-3-benzofurancarboxylic acid ethyl ester;NSC42354;UNII-7ZX8M4JY4M;Oprea1_791351;CBDivE_004339;cid_81704;ethyl 5-hydroxy-2-methylbenzo[b]furan-3-carboxylate;CHEMBL473809;SCHEMBL24470667;BDBM46464;DTXSID10223167;HMS1577F17;HMS2358L07;AC6693;BBL000026;NSC 42354;STK279510;AKOS000267125;NCGC00245557-01;NS-02644;SY045646;BB 0262086;CS-0245383;FT-0682981;UNM000007740102;EN300-30416;2-METHYL-3-CARBOETHOXY-5-ETHOXYBENZOFURAN;A866189;AG-219/03618014;SR-01000487958;SR-01000487958-1;ethyl 2-methyl-5-oxidanyl-1-benzofuran-3-carboxylate;Z57301064;F1387-0004;3-Benzofurancarboxylic acid, 5-hydroxy-2-methyl-, ethyl ester

Chemical Property of Ethyl 5-hydroxy-2-methyl-1-benzofuran-3-carboxylate

Chemical Property:

• PSA: 59.67000
• LogP: 2.62350
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 220.07355886
• Heavy Atom Count: 16
• Complexity: 266

Purity/Quality:

99% ^*data from raw suppliers

Ethyl5-Hydroxy-2-methyl-1-benzofuran-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(OC2=C1C=C(C=C2)O)C

Technology Process of Ethyl 5-hydroxy-2-methyl-1-benzofuran-3-carboxylate

There total 8 articles about Ethyl 5-hydroxy-2-methyl-1-benzofuran-3-carboxylate 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%

ethyl acetoacetate (141-97-9) + p-benzoquinone (106-51-4) → ethyl 5-hydroxy-2-methyl-benzofuran-3-carboxylate (7287-40-3)

Guidance literature:

With zinc(II) chloride; at 80 ℃; for 12h;

Reference yield: 70.0%

α-(Hydrochinonyl)-β-(methylamino)-crotonsaeureethylester (75785-33-0) → ethyl 5-hydroxy-2-methyl-benzofuran-3-carboxylate (7287-40-3)

Guidance literature:

With trifluoroacetic acid; In benzene; for 4h; Heating;

DOI:10.1002/jhet.5570430410

Reference yield: 31.0%

ethyl acetoacetate (141-97-9) + p-benzoquinone (106-51-4) → ethyl 5-hydroxy-2-methyl-benzofuran-3-carboxylate (7287-40-3) + diethyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate (7674-99-9)

Guidance literature:

With zinc(II) chloride;

DOI:10.1016/j.bmcl.2009.02.082

upstream raw materials:

ethyl acetoacetate

p-benzoquinone

α-(Hydrochinonyl)-β-(methylamino)-crotonsaeureethylester

ethyl N-methyl-β-aminocrotonate

Downstream raw materials:

5-methoxy-2-methylbenzofuran

5-methoxy-2-methylbenzofuran-3-carboxylic acid

C₂₄H₁₅BrN₂O₇S

C₂₅H₁₈BrNO₆S

Refernces

• 1、 Bruno, Ferdinando,Errico, Suann,Pace, Simona,Nawrozkij, Maxim B.,Mkrtchyan, Arthur S.,Guida, Francesca,Maisto, Rosa,Olga?, Abdurrahman,D'Amico, Michele,Maione, Sabatino,De Rosa, Mario,Banoglu, Erden,Werz, Oliver,Fiorentino, Antonio,Filosa, Rosanna. "Structural insight into the optimization of ethyl 5-hydroxybenzo[g]indol-3-carboxylates and their bioisosteric analogues as 5-LO/m-PGES-1 dual inhibitors able to suppress inflammation". . p. 946 - 960. Retrieved 2018/07/24.
• 2、 Yadav, Pratima,Singh, Praveen,Tewari, Ashish Kumar. "Design, synthesis, docking and anti-inflammatory evaluation of novel series of benzofuran based prodrugs". supporting information. p. 2251 - 2255. Retrieved 2014/05/20.