3-(3-Phenyl-1,2,4-oxadiazol-5-yl)propanoic acid

Base Information

• Chemical Name: 3-(3-Phenyl-1,2,4-oxadiazol-5-yl)propanoic acid
• CAS No.: 24088-59-3
• Molecular Formula: C11H10 N2 O3
• Molecular Weight: 218.212
• Hs Code.: 2934999090
• European Community (EC) Number: 854-386-8
• DSSTox Substance ID: DTXSID30349838
• Nikkaji Number: J1.204.333C
• Wikidata: Q82125346
• ChEMBL ID: CHEMBL1313027
• Mol file: 24088-59-3.mol

Synonyms:3-(3-phenyl-1,2,4-oxadiazol-5-yl)propionic acid;3-Ph-OPA

Chemical Property of 3-(3-Phenyl-1,2,4-oxadiazol-5-yl)propanoic acid

Chemical Property:

• Vapor Pressure: 2.79E-08mmHg at 25°C
• Melting Point: 119-120 °C(Solv: chloroform (67-66-3))
• Boiling Point: 433.4°Cat760mmHg
• PKA: 4.07±0.10(Predicted)
• Flash Point: 215.9°C
• PSA: 76.22000
• Density: 1.299g/cm³
• LogP: 1.75380
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 218.06914219
• Heavy Atom Count: 16
• Complexity: 241

Purity/Quality:

98%min ^*data from raw suppliers

3-(3-Phenyl-1,2,4-oxadiazol-5-yl)propanoic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NOC(=N2)CCC(=O)O
• Uses: 3-(3-Phenyl-1,2,4-oxadiazol-5-yl)propanoic Acid is a useful reactant for N-arylamide oxadiazole preparation as selective oral CB2 agonists.

Technology Process of 3-(3-Phenyl-1,2,4-oxadiazol-5-yl)propanoic acid

There total 7 articles about 3-(3-Phenyl-1,2,4-oxadiazol-5-yl)propanoic 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: 90.0%

4-(((amino(phenyl)methylene)amino)oxy)-4-oxobutanoic acid (1175001-94-1) → 3-<(3-Phenyl)-1,2,4-oxadiazol-5-yl>propionic acid (24088-59-3)

Guidance literature:

With sodium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 1h; Reagent/catalyst;

DOI:10.1016/j.tetlet.2017.08.020

Reference yield: 87.0%

succinic acid anhydride (108-30-5) + N-hydroxybenzenecarboximidamide (613-92-3) → 3-<(3-Phenyl)-1,2,4-oxadiazol-5-yl>propionic acid (24088-59-3)

Guidance literature:

In 1,4-dioxane; at 200 ℃; for 0.166667h;

Reference yield: 73.0%

succinic acid anhydride (108-30-5) + N-hydroxybenzenecarboximidamide (613-92-3) → 5,5'-(1,2-ethanediyl)-bis<3-(phenyl)-1,2,4-oxadiazole> (22020-64-0) + 3,5-diphenyl-1,2,4-oxadiazole (888-71-1) + 3-<(3-Phenyl)-1,2,4-oxadiazol-5-yl>propionic acid (24088-59-3)

Guidance literature:

at 140 ℃; for 0.0333333h; Microwave irradiation; Sealed vessel;

DOI:10.1248/cpb.57.819

upstream raw materials:

succinic acid anhydride

N-hydroxybenzenecarboximidamide

N-hydroxyl-benzamidine

benzonitrile

Downstream raw materials:

3-(phenyl-1,2,4-oxadiazol-5-yl)propionyl chloride

3-(3-phenyl-1,2,4-oxadiazol-5-yl)propanol

Refernces

• 1、 Neves Filho, Ricardo A. W.,Srivastava, Rajendra M.. "A handy and solventless direct route to primary 3-[3-aryl-1,2,4-oxadiazol- 5-yl]propionamides using microwave irradiation". . p. 318 - 324. Retrieved 2006.
• 2、 Jadhav, Ganesh R.,Shaikh, Mohammad U.,Kale, Rajesh P.,Ghawalkar, Anand R.,Gill, Charansingh H.. "Synthesis, characterization, and antimicrobial activities of clubbed [1,2,4]-oxadiazoles with fluorobenzimidazoles". experimental part. p. 980 - 987. Retrieved 2009/12/05.
• 3、 Cheng, Yuan,Albrecht, Brian K.,Brown, James,Buchanan, John L.,Buckner, William H.,DiMauro, Erin F.,Emkey, Renee,Fremeau Jr., Robert T.,Harmange, Jean-Christophe,Hoffman, Beth J.,Huang, Liyue,Huang, Ming,Lee, Josie Han,Lin, Fen-Fen,Martin, Matthew W.,Nguyen, Hung Q.,Patel, Vinod F.,Tomlinson, Susan A.,White, Ryan D.,Xia, Xiaoyang,Hitchcock, Stephen A.. "Discovery and optimization of a novel series of N-arylamide oxadiazoles as potent, highly selective and orally bioavailable cannabinoid receptor 2 (CB 2) agonists". experimental part. p. 5019 - 5034. Retrieved 2009/07/19.