5-(4-cyanophenyl)furan-2-carboxylic Acid

Base Information

• Chemical Name: 5-(4-cyanophenyl)furan-2-carboxylic Acid
• CAS No.: 52938-94-0
• Molecular Formula: C12H7NO3
• Molecular Weight: 213.192
• Hs Code.: 2932190090
• European Community (EC) Number: 879-137-0
• DSSTox Substance ID: DTXSID10400552
• Wikidata: Q82203560
• ChEMBL ID: CHEMBL4166368
• Mol file: 52938-94-0.mol

Synonyms:5-(4-cyanophenyl)furan-2-carboxylic Acid;52938-94-0;5-(4-Cyanophenyl)-2-furoic acid;5-(4-CYANOPHENYL)-FURANE-2-CARBOXYLIC ACID;SCHEMBL3416828;CHEMBL4166368;DTXSID10400552;BBL034399;MFCD06802004;STL412031;AKOS004117334;5-(4-cyanophenyl)furan-2-carboxylicAcid;AS-40661;BB 0223019;CS-0217441;5-(4-Cyanophenyl)-2-furoic acid, AldrichCPR;EN300-745788

Chemical Property of 5-(4-cyanophenyl)furan-2-carboxylic Acid

Chemical Property:

• PSA: 74.23000
• LogP: 2.51648
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 213.042593085
• Heavy Atom Count: 16
• Complexity: 312

Purity/Quality:

99% ^*data from raw suppliers

5-(4-Cyanophenyl)-2-furoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)C2=CC=C(O2)C(=O)O
• Uses: 5-(4-Cyanophenyl)-2-furoic Acid is a reagent in the preparation of dihydrooxadiazole series of non-ATP-competitive MK2 inhibitors as a method for the development of cures for inflammatory diseases like arthritis.

Technology Process of 5-(4-cyanophenyl)furan-2-carboxylic Acid

There total 7 articles about 5-(4-cyanophenyl)furan-2-carboxylic 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: 95.0%

5-(4-cyanophenyl)furan-2-carboxylic acid methyl ester (834884-75-2) → 5-(4-cyanophenyl)furan-2-carboxylic acid (52938-94-0)

Guidance literature:

With methanol; sodium hydroxide; for 3h; Reflux;

Reference yield: 30.0%

2-furanoic acid (88-14-2) + 4-Aminobenzonitrile (873-74-5) → 5-(4-cyanophenyl)furan-2-carboxylic acid (52938-94-0)

Guidance literature:

4-Aminobenzonitrile; With hydrogenchloride; sodium nitrite; In water;

2-furanoic acid; In water; acetone; at 25 - 30 ℃;

DOI:10.1002/1521-4184(200107)334:7<235::AID-ARDP235>3.0.CO;2-#

Reference yield:

5-bromo-furan-2-carboxylic acid (585-70-6) + 4-cyanophenylboronic acid (126747-14-6) → 5-(4-cyanophenyl)furan-2-carboxylic acid (52938-94-0)

Guidance literature:

With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride; In water; isopropyl alcohol; for 3h; Heating;

DOI:10.1021/jm070637u

upstream raw materials:

2-furanoic acid

4-Aminobenzonitrile

5-bromo-furan-2-carboxylic acid

4-cyanophenylboronic acid

Downstream raw materials:

ethyl 5-(4-cyanophenyl)-2-furancarboxylate

C₁₉H₁₄N₂O₂

5-(4'-carboxyphenyl)-2-furanylcarboxylic acid

4-(5-(4-(4-(piperazin-1-yl)phenyl)-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)furan-2-yl)benzonitrile

Refernces

• 1、 Chiarelli, Laurent R.,Mori, Matteo,Barlocco, Daniela,Beretta, Giangiacomo,Gelain, Arianna,Pini, Elena,Porcino, Marianna,Mori, Giorgia,Stelitano, Giovanni,Costantino, Luca,Lapillo, Margherita,Bonanni, Davide,Poli, Giulio,Tuccinardi, Tiziano,Villa, Stefania,Meneghetti, Fiorella. "Discovery and development of novel salicylate synthase (MbtI) furanic inhibitors as antitubercular agents". . p. 754 - 763. Retrieved 2018/06/26.
• 2、 Kort, Michael E.,Drizin, Irene,Gregg, Robert J.,Scanio, Marc J. C.,Shi, Lei,Gross, Michael F.,Atkinson, Robert N.,Johnson, Matthew S.,Pacofsky, Gregory J.,Thomas, James B.,Carroll, William A.,Krambis, Michael J.,Liu, Dong,Shieh, Char-Chang,Zhang, XuFeng,Hernandez, Gricelda,Mikusa, Joseph P.,Zhong, Chengmin,Joshi, Shailen,Honore, Prisca,Roeloffs, Rosemarie,Marsh, Kennan C.,Murray, Bernard P.,Liu, Jinrong,Werness, Stephen,Faltynek, Connie R.,Krafte, Douglas S.,Jarvis, Michael F.,Chapman, Mark L.,Marron, Brian E.. "Discovery and biological evaluation of 5-aryl-2-furfuramides, potent and selective blockers of the Nav1.8 sodium channel with efficacy in models of neuropathic and inflammatory pain". . p. 407 - 416. Retrieved 2008/09/18.