(e)-3-(2,3-Dihydrobenzofuran-5-yl)acrylic acid

Base Information

• Chemical Name: (e)-3-(2,3-Dihydrobenzofuran-5-yl)acrylic acid
• CAS No.: 203505-84-4
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.199
• Hs Code.: 2932999099
• European Community (EC) Number: 814-116-1,674-352-4
• DSSTox Substance ID: DTXSID901220678
• Wikidata: Q76310619
• Mol file: 203505-84-4.mol

Synonyms:203505-84-4;198707-57-2;(e)-3-(2,3-dihydrobenzofuran-5-yl)acrylic acid;(2E)-3-(2,3-Dihydrobenzofuran-5-yl)propenoic acid;2-Propenoic acid, 3-(2,3-dihydro-5-benzofuranyl)-;(E)-3-(2,3-dihydro-1-benzofuran-5-yl)prop-2-enoic acid;3-(2,3-dihydrobenzofuran-5-yl)-2-propenoic acid;(2E)-3-(2,3-dihydro-1-benzofuran-5-yl)prop-2-enoic acid;(E)-3-(2,3-dihydrobenzofuran-5-yl)-2-propenoic acid;3-(2,3-dihydro-1-benzofuran-5-yl)acrylic acid;3-(2,3-dihydro-1-benzofuran-5-yl)prop-2-enoic acid;SCHEMBL2717768;SCHEMBL2717774;(2E)-3-(2,3-dihydro-1-benzofuran-5-yl)acrylic acid;KNKNRFWCOVWKHJ-DUXPYHPUSA-N;2-Propenoic acid, 3-(2,3-dihydro-5-benzofuranyl)-, (2E)-;DTXSID901220678;CS-M3381;YHA70757;AKOS001295734;AKOS025312262;GC-0728;3-(2,3-Dihydrobenzofuran-5-yl)acrylicacid;3-(2,3-Dihydrobenzofuran-5-yl)acrylic acid;EN300-25620;C12982;EN300-270447;3-(2,3-dihydro-5-benzofuranyl)-2-propenoic acid;A814473;J-500749;J-501870;(E)-3-(2,3-Dihydrobenzo[b]furan-5-yl)acrylic acid;(2E)-3-(2,3-Dihydro-5-benzofuranyl)-2-propenoic acid;(2e)-3-(2,3-dihydrobenzo[b]furan-5-yl)propenoic acid;trans-3-(2,3-dihydrobenzofuran-5-yl)prop-2-enoic acid;Z2942851993;(2E)-3-(2,3-DIHYDROBENZOFURAN-5-YL)PROPENOICACID;2-Propenoic acid,3-(2,3-dihydro-5-benzofuranyl)-,(2E)-

Chemical Property of (e)-3-(2,3-Dihydrobenzofuran-5-yl)acrylic acid

Chemical Property:

• Vapor Pressure: 1.92E-06mmHg at 25°C
• Melting Point: 170-173°C
• Boiling Point: 379.8°Cat760mmHg
• Flash Point: 154.7°C
• PSA: 46.53000
• Density: 1.31g/cm³
• LogP: 1.71930
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 190.062994177
• Heavy Atom Count: 14
• Complexity: 247

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2E)-3-(2,3-Dihydrobenzofuran-5-yl)propenoicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2=C1C=C(C=C2)C=CC(=O)O
• Isomeric SMILES: C1COC2=C1C=C(C=C2)/C=C/C(=O)O

Technology Process of (e)-3-(2,3-Dihydrobenzofuran-5-yl)acrylic acid

There total 3 articles about (e)-3-(2,3-Dihydrobenzofuran-5-yl)acrylic acid 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: 78.0%

2,3-dihydro-benzofuran-5-carbaldehyde (55745-70-5) + malonic acid (141-82-2) → 3-(2,3-dihydro-1-benzofuran-5-yl)-2-propenoic acid (203505-84-4)

Guidance literature:

With piperidine; pyridine; at 100 ℃; for 5h;

Reference yield:

5-bromo-2,3-dihydrobenzo[b]furan (66826-78-6) + palladium tetrakistriphenylphosphine + 3-(2,3-dihydro-benzo[b]furan-5-yl)acrylic acid tert butyl ester + tert-Butyl acrylate (1663-39-4,25232-27-3) → 3-(2,3-dihydro-1-benzofuran-5-yl)-2-propenoic acid (203505-84-4)

Guidance literature:

With formic acid; triethylamine; trifluoroacetic acid; In n-heptane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

Reference yield:

2.3-dihydrobenzofuran (496-16-2) → 3-(2,3-dihydro-1-benzofuran-5-yl)-2-propenoic acid (203505-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / TiCl₄ / CH₂Cl₂ / 1 h

2: 62 percent / pyridine; piperidine / 4 h / 100 °C

With piperidine; pyridine; titanium tetrachloride; In dichloromethane; 1: Vilsmeier-Haack reaction;

DOI:10.1021/jm0201159

upstream raw materials:

2,3-dihydro-benzofuran-5-carbaldehyde

malonic acid

2.3-dihydrobenzofuran

5-bromo-2,3-dihydrobenzo[b]furan

Downstream raw materials:

3-(2,3-dihydro-1-benzofuran-5-yl)propanoic acid

2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-one

2-(2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-ylidene)acetonitrile

2-(3,5,6,7-tetrahydro-2H-indeno[5,6-b]furan-7-yl)ethylamine

Refernces

• 1、 -. "SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME". Page/Page column 149. . Retrieved 2016/09/15.
• 2、 Uchikawa, Osamu,Fukatsu, Kohji,Tokunoh, Ryosuke,Kawada, Mitsuru,Matsumoto, Kiyoharu,Imai, Yumi,Hinuma, Shuji,Kato, Koki,Nishikawa, Hisao,Hirai, Keisuke,Miyamoto, Masaomi,Ohkawa, Shigenori. "Synthesis of a novel series of tricyclic indan derivatives as melatonin receptor agonists". . p. 4222 - 4239. Retrieved 2007/10/03.