Diethyl furfurylidenemalonate

Base Information

• Chemical Name: Diethyl furfurylidenemalonate
• CAS No.: 17448-96-3
• Molecular Formula: C12H14 O5
• Molecular Weight: 238.24
• Hs Code.: 2932190090
• European Community (EC) Number: 241-463-0
• NSC Number: 643042,406758
• UNII: A6EE0FM7AQ
• DSSTox Substance ID: DTXSID00169828
• Nikkaji Number: J41.610J
• Mol file: 17448-96-3.mol

Synonyms:17448-96-3;Diethyl furfurylidenemalonate;DIETHYL FURFURYLIDENE MALONATE;Diethyl 2-furfurylidenemalonate;Diethyl 2-(furan-2-ylmethylene)malonate;MALONIC ACID, FURFURYLIDENE-, DIETHYL ESTER;diethyl 2-(furan-2-ylmethylidene)propanedioate;EINECS 241-463-0;A6EE0FM7AQ;NSC 406758;BRN 0211365;2-Furfurylidenemalonic acid diethyl ester;Propanedioic acid, (2-furanylmethylene)-, diethyl ester;AI3-05656;Propanedioic acid, 2-furfurylidene-, diethyl ester;Diethyl 2-(2-furylmethylene)malonate;NSC643042;NSC-406758;NSC-643042;5-18-07-00090 (Beilstein Handbook Reference);UNII-A6EE0FM7AQ;SCHEMBL11781592;DTXSID00169828;WLN: T5OJ B1UYVO2&VO2;Diethyl (2-furylmethylene)malonate;MFCD00020981;NSC406758;STK795755;AKOS001748410;diethyl 2-(2-furylmethylene)propanedioate;LS-88821;diethyl (furan-2-ylmethylidene)propanedioate;1,3-diethyl 2-[(furan-2-yl)methylidene]propanedioate;2-(furan-2-yl-methylene)-propanedioic acid diethyl ester;PROPANEDIOIC ACID, 2-(2-FURANYLMETHYLENE)-, 1,3-DIETHYL ESTER

Chemical Property of Diethyl furfurylidenemalonate

Chemical Property:

• Vapor Pressure: 0.00265mmHg at 25°C
• Melting Point: 140-141 °C(Solv: chloroform (67-66-3))
• Boiling Point: 286.4°Cat760mmHg
• Flash Point: 127°C
• PSA: 65.74000
• Density: 1.176g/cm³
• LogP: 1.78920
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 238.08412354
• Heavy Atom Count: 17
• Complexity: 288

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=CC1=CC=CO1)C(=O)OCC

Technology Process of Diethyl furfurylidenemalonate

There total 11 articles about Diethyl furfurylidenemalonate 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: 98.0%

furfural (98-01-1) + diethyl malonate (105-53-3) → ethyl 2-carbethoxy-3-(2-furanyl)propenoate (17448-96-3)

Guidance literature:

With piperidine; acetic acid; In ethanol; for 48h; Reflux;

DOI:10.1002/ejoc.202100430

Reference yield: 98.0%

9-Furan-2-yl-7,10-dithia-cyclohepta[de]naphthalene-8,8-dicarboxylic acid diethyl ester (181023-32-5) → ethyl 2-carbethoxy-3-(2-furanyl)propenoate (17448-96-3) + 1,8-naphthalenedisulfide (209-22-3)

Guidance literature:

In dichloromethane; Irradiation;

DOI:10.1021/jo960517m

Reference yield: 81.0%

furfural (98-01-1) + Diethyl 2-bromomalonate (685-87-0) → ethyl 2-carbethoxy-3-(2-furanyl)propenoate (17448-96-3)

Guidance literature:

With tri-n-butylarsine; at 80 ℃; for 11h;

DOI:10.1016/0022-328X(89)85082-X

upstream raw materials:

piperidine

furfural

diethyl malonate

acetic anhydride

Downstream raw materials:

C₂₄H₂₅O₅P

(2S,3S)-1,1-diethyl 3-methyl 3-(diphenylmethyleneamino)-2-(furan-2-yl)propane-1,1,3-tricarboxylate

bis[(S)-4-phenylthiazoline-2-yl]-2-furylethene

bis[(S)-4-benzylthiazoline-2-yl]-2-furylethene

Refernces

• 1、 Van Schijndel, Jack,Canalle, Luiz Alberto,Molendijk, Dennis,Meuldijk, Jan. "Exploration of the Role of Double Schiff Bases as Catalytic Intermediates in the Knoevenagel Reaction of Furanic Aldehydes: Mechanistic Considerations". . p. 1983 - 1988. Retrieved 2018.
• 2、 Shirotori, Mahiro,Nishimura, Shun,Ebitani, Kohki. "One-pot synthesis of furfural derivatives from pentoses using solid acid and base catalysts". . p. 971 - 978. Retrieved 2014.
• 3、 Kazia, Armands,Melngaile, Renate,Mishnev, Anatoly,Veliks, Janis. "Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes: Scope and limitations". supporting information. p. 1384 - 1388. Retrieved 2020/03/03.