4-(5-Methyl-1,3,4-oxadiazol-2-YL)phenol

Base Information

• Chemical Name: 4-(5-Methyl-1,3,4-oxadiazol-2-YL)phenol
• CAS No.: 25877-46-7
• Molecular Formula: C9H8N2O2
• Molecular Weight: 176.175
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20421950
• Wikidata: Q82233692
• Mol file: 25877-46-7.mol

Synonyms:4-(5-METHYL-1,3,4-OXADIAZOL-2-YL)PHENOL;25877-46-7;4-(5-methyl-1,3,4-oxadiazol-2-yl)phenol(SALTDATA: FREE);SCHEMBL8058008;DTXSID20421950;ZGERZQXLBGWDCL-UHFFFAOYSA-N;MFCD04126174;AKOS005102330;BB 0238209;CS-0084215;FT-0765376;4-(5-Methyl-[1,3,4]oxadiazol-2-yl)-phenol;4-(5-methyl-1, 3, 4-oxadiazol-2-yl)phenol;F16171;8W-0877;4-(5-methyl-1,3,4-oxadiazol-2-yl)phenol, AldrichCPR

Chemical Property of 4-(5-Methyl-1,3,4-oxadiazol-2-YL)phenol

Chemical Property:

• Vapor Pressure: 1.82E-05mmHg at 25°C
• Melting Point: 236 °C(Solv: ethanol (64-17-5))
• Boiling Point: 352.9°C at 760 mmHg
• PKA: 8.17±0.15(Predicted)
• Flash Point: 167.2°C
• PSA: 59.15000
• Density: 1.27g/cm³
• LogP: 1.75060
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 176.058577502
• Heavy Atom Count: 13
• Complexity: 169

Purity/Quality:

NLT 98% ^*data from raw suppliers

4-(5-methyl-1,3,4-oxadiazol-2-yl)phenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN=C(O1)C2=CC=C(C=C2)O

Technology Process of 4-(5-Methyl-1,3,4-oxadiazol-2-YL)phenol

There total 9 articles about 4-(5-Methyl-1,3,4-oxadiazol-2-YL)phenol 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: 83.0%

Nitroethane (79-24-3) + 4-hydroxybenzoic acid hydrazide (5351-23-5) → 4-(5-methyl-1,3,4-oxadiazol-2-yl)phenol (25877-46-7)

Guidance literature:

With polyphosphoric acid; at 105 - 115 ℃; for 1.5h; chemoselective reaction;

DOI:10.1039/c9ra00976k

Reference yield: 55.0%

methyl 4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl ether (25877-54-7) → 4-(5-methyl-1,3,4-oxadiazol-2-yl)phenol (25877-46-7)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 72h;

DOI:10.1016/S0928-0987(02)00024-6

Reference yield:

methyl 4-methoxybenzoate (121-98-2) → 4-(5-methyl-1,3,4-oxadiazol-2-yl)phenol (25877-46-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / hydrazine monohydrate / 3 h / 120 °C

2: 66 percent / 120 - 140 °C

3: 55 percent / BBr₃ / CH₂Cl₂ / 72 h / 20 °C

With boron tribromide; hydrazine hydrate; In dichloromethane;

DOI:10.1016/S0928-0987(02)00024-6

upstream raw materials:

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

methyl 4-methoxybenzoate

4-methoxybenzoic acid hydrazide

4-hydroxybenzoic acid hydrazide

Downstream raw materials:

4-(5-methyl-1,3,4-oxadiazol-2-yl)benzaldehyde

4-(5-methyl-1,3,4-oxazdiazol-2-yl)benzoic acid

Refernces

• 1、 Aksenov, Alexander V.,Khamraev, Vladislav,Aksenov, Nicolai A.,Kirilov, Nikita K.,Domenyuk, Dmitriy A.,Zelensky, Vladimir A.,Rubin, Michael. "Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles". . p. 6636 - 6642. Retrieved 2019/03/14.
• 2、 Sadek, Bassem,Fahelelbom, Khairi Mustafa Salem. "Synthesis, characterization, and antimicrobial evaluation of oxadiazole congeners". experimental part. p. 4339 - 4347. Retrieved 2011/08/10.