Ethyl 5-formyl-2-methylfuran-3-carboxylate

Base Information

• Chemical Name: Ethyl 5-formyl-2-methylfuran-3-carboxylate
• CAS No.: 19615-48-6
• Molecular Formula: C9H10 O4
• Molecular Weight: 182.176
• NSC Number: 170829
• DSSTox Substance ID: DTXSID20305463
• Nikkaji Number: J1.726.695K
• Wikidata: Q82052105
• Mol file: 19615-48-6.mol

Synonyms:ethyl 5-formyl-2-methylfuran-3-carboxylate;19615-48-6;NSC170829;5-methyl-4-carbethoxyfurfural;SCHEMBL5357960;DTXSID20305463;NSC-170829;ethyl5-formyl-2-methylfuran-3-carboxylate;EN300-673344

Chemical Property of Ethyl 5-formyl-2-methylfuran-3-carboxylate

Chemical Property:

• Vapor Pressure: 0.00222mmHg at 25°C
• Boiling Point: 289.3°Cat760mmHg
• Flash Point: 128.7°C
• Density: 1.178g/cm³
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(OC(=C1)C=O)C

Technology Process of Ethyl 5-formyl-2-methylfuran-3-carboxylate

There total 17 articles about Ethyl 5-formyl-2-methylfuran-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: 86.0%

ethyl 2-methyl-5-(D-arabino-tetritol-1-yl)furan-3-carboxylate (3351-43-7) → 5-formyl-2-methyl-furan-3-carboxylic acid ethyl ester (19615-48-6)

Guidance literature:

With sodium periodate; In methanol; water; at 0 - 20 ℃; for 0.666667h;

Reference yield: 85.0%

ethyl 2-methyl-5-methylene-4,5-dihydrofuran-3-carboxylate (122132-58-5) → ethyl 2-methyl-5-hydroxymethylfuran-3-carboxylate (15341-70-5) + 5-formyl-2-methyl-furan-3-carboxylic acid ethyl ester (19615-48-6) + 5-(hydroperoxymethyl)-3-ethoxycarbonyl-2-methylfuran (130533-18-5)

Guidance literature:

With oxygen; rose bengal; at 20 ℃; Irradiation;

DOI:10.1016/S0040-4020(97)10135-1

Reference yield: 82.0%

5-(hydroperoxymethyl)-3-ethoxycarbonyl-2-methylfuran (130533-18-5) → 5-formyl-2-methyl-furan-3-carboxylic acid ethyl ester (19615-48-6)

Guidance literature:

for 2h; Ambient temperature; soybean lipoxygenase, borate buffer, pH=9;

DOI:10.1016/S0040-4039(00)74178-5

upstream raw materials:

ethanol

D-ribose

ethyl acetoacetate

(E)-3-Ureido-but-2-enoic acid ethyl ester

Downstream raw materials:

C₂₃H₂₀N₄O₆

C₁₆H₁₄N₂O₄

C₁₇H₁₆N₂O₅

C₁₆H₁₃ClN₂O₄

Refernces

• 1、 Pevzner, L. M.,Stepanova, N. P.. "Synthesis of (2-Ethoxy-2-oxoethylthio)methyl Derivatives of Furoic Acids and Attempts of Their Intramolecular Cyclizations under the Conditions of the Claisen Reaction". . p. 166 - 181. Retrieved 2020.
• 2、 Saito, Akio. "Metal-free syntheses of oxazoles and their analogues based on λ3-iodane-mediated cycloisomerization/functionalization reactions or [2+2+1] cycloaddition type reactions". . p. 84 - 98. Retrieved 2017/04/17.