Ethyl 5-chlorobenzofuran-2-carboxylate

Base Information

• Chemical Name: Ethyl 5-chlorobenzofuran-2-carboxylate
• CAS No.: 59962-89-9
• Molecular Formula: C₁₁H₉ClO₃
• Molecular Weight: 224.644
• Hs Code.: 29321900
• DSSTox Substance ID: DTXSID00384059
• Wikidata: Q72473495
• Mol file: 59962-89-9.mol

Synonyms:Ethyl 5-chlorobenzofuran-2-carboxylate;59962-89-9;ethyl 5-chloro-1-benzofuran-2-carboxylate;5-Chloro-benzofuran-2-carboxylic acid ethyl ester;MFCD00275273;Maybridge3_000216;SCHEMBL5023676;DTXSID00384059;KTBFFSXNFOOSEH-UHFFFAOYSA-N;HMS1431J18;AC6446;ethyl-5-chloro-benzofuran carboxylate;STK137568;AKOS000371654;CCG-233538;ethyl 5-chlorobenzofuran-2-car-boxylate;IDI1_011603;AS-63887;SY045681;ethyl 5-chlorobenzo[b]furan-2-carboxylate;FT-0706755;5-Chlorobenzofuran-2-carboxylic acid ethyl ester;A832555;J-517389

Chemical Property of Ethyl 5-chlorobenzofuran-2-carboxylate

Chemical Property:

• Boiling Point: 308.5 °C at 760 mmHg
• Flash Point: 140.4 °C
• PSA: 39.44000
• Density: 1.3 g/cm³
• LogP: 3.26290
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 224.0240218
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

98%Min ^*data from raw suppliers

Ethyl5-chlorobenzofuran-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(O1)C=CC(=C2)Cl

Technology Process of Ethyl 5-chlorobenzofuran-2-carboxylate

There total 9 articles about Ethyl 5-chlorobenzofuran-2-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: 84.8%

ethyl bromoacetate (105-36-2) + 5-chlorosalicyclaldehyde (635-93-8) → ethyl 5-chlorobenzofuran-2-carboxylate (59962-89-9)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; acetonitrile; for 48h; Reflux;

Reference yield: 82.0%

ethanol (64-17-5) + 4-chloro-2-<2',2'-dibromo ethenyl>-phenol (95186-48-4) + molybdenum hexacarbonyl (13939-06-5,199620-15-0) → ethyl 5-chlorobenzofuran-2-carboxylate (59962-89-9)

Guidance literature:

With [2,2]bipyridinyl; triethylamine; copper(ll) bromide; at 90 ℃; for 8h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.0c01620

Reference yield: 66.0%

Diethyl 2-bromomalonate (685-87-0) + 5-chlorosalicyclaldehyde (635-93-8) → ethyl 5-chlorobenzofuran-2-carboxylate (59962-89-9)

Guidance literature:

With potassium carbonate;

DOI:10.1211/0022357991772637

upstream raw materials:

Diethyl 2-bromomalonate

5-chlorosalicyclaldehyde

ethyl bromoacetate

3-chlorosalicylaldehyde

Downstream raw materials:

(+/-)-5-chloro-2,3-dihydro-1-benzofuran-2-carboxylic acid

5-chlorobenzofuran-2-carboxylic acid

Refernces

• 1、 Kong, Ling-Yi,Leng, Jia-Fu,Lian, Bao-Ping,Shao, Yu-Ying,Xia, Yuan-Zheng,Yin, Yong. "Synthesis and biological evaluation of novel shikonin-benzo[b]furan derivatives as tubulin polymerization inhibitors targeting the colchicine binding site". . . Retrieved 2020/02/11.
• 2、 -. "Halogenated benzofuran-coumarin derivative and application thereof to preparation of anti-fouling agent". Paragraph 0023-0025. . Retrieved 2019/09/17.