Diethyl 3,4-furandicarboxylate

Base Information

• Chemical Name: Diethyl 3,4-furandicarboxylate
• CAS No.: 30614-77-8
• Molecular Formula: C10H12O5
• Molecular Weight: 212.202
• Hs Code.: 29321900
• European Community (EC) Number: 250-262-7
• DSSTox Substance ID: DTXSID30184680
• Nikkaji Number: J75.471D
• Wikidata: Q72461947
• Mol file: 30614-77-8.mol

Synonyms:Diethyl 3,4-furandicarboxylate;30614-77-8;Diethyl furan-3,4-dicarboxylate;3,4-FURANDICARBOXYLIC ACID, DIETHYL ESTER;EINECS 250-262-7;BRN 0170398;MFCD00005349;furan-3,4-dicarboxylic acid diethyl ester;5-18-07-00053 (Beilstein Handbook Reference);3,4-diethyl furan-3,4-dicarboxylate;SCHEMBL2036542;ZODFWNHYQARJLC-UHFFFAOYSA-;DTXSID30184680;AKOS005174970;SB61518;AS-31238;LS-70194;SY005437;CS-0314135;FT-0600450;A876138;J-640063;J-800064

Chemical Property of Diethyl 3,4-furandicarboxylate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 0.00247mmHg at 25°C
• Refractive Index: n20/D 1.47(lit.)
• Boiling Point: 287.6 °C at 760 mmHg
• Flash Point: 107.8 °C
• PSA: 65.74000
• Density: 1.172 g/cm³
• LogP: 1.63300
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 212.06847348
• Heavy Atom Count: 15
• Complexity: 214

Purity/Quality:

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

Diethyl3,4-furandicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=COC=C1C(=O)OCC

Technology Process of Diethyl 3,4-furandicarboxylate

There total 13 articles about Diethyl 3,4-furandicarboxylate 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: 81.0%

diethyl 2,5-dihydrofuran-3,4-dicarboxylate (479035-73-9) → diethyl 3,4-furandicarboxylate (30614-77-8)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; for 24h; Heating;

DOI:10.1055/s-2002-31967

Reference yield:

diethyl 2-formyl-3-(diethoxymethyl)succinate (73926-95-1) → diethyl 3,4-furandicarboxylate (30614-77-8)

Guidance literature:

With hydrogen fluoride;

Reference yield:

2,3-Dimethylmaleic anhydride (766-39-2) → diethyl 3,4-furandicarboxylate (30614-77-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / NBS; dibenzoyl peroxide / CCl₄ / 24 h / Heating

2: 98 percent / aq. KOH / 3 h / 20 °C

3: 91 percent / Ph₃P; DEAD / tetrahydrofuran / 3 h / 20 °C

4: 88 percent / H₂SO₄ / 24 h / 20 °C

5: 81 percent / DDQ / dioxane / 24 h / Heating

With potassium hydroxide; N-Bromosuccinimide; sulfuric acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; dibenzoyl peroxide; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; 3: intramolecular Mitsunobu ring closure;

DOI:10.1055/s-2002-31967

upstream raw materials:

furan-3,4-dicarboxylic acid

ethanol

diethyl 2-formyl-3-(diethoxymethyl)succinate

7-oxa-norborn-2-ene-2,3-dicarboxylic acid diethyl ester

Downstream raw materials:

3,4-bis(hydroxymethyl)furan

furan-3,4-dicarboxylic acid

Furan-3,4-dicarbonsaeurehydrazid

3,4-Furandicarboxylic Acid Monoethyl Ester

Refernces

• 1、 Koenig, Horst,Graf, Fritz,Weberndoerfer, Volkmar. "A New and Versatile Synthesis of Furans". . p. 668 - 682. Retrieved 2007/10/02.