Toloxatone

Base Information

• Chemical Name: Toloxatone
• CAS No.: 29218-27-7
• Molecular Formula: C11H13 N O3
• Molecular Weight: 207.229
• European Community (EC) Number: 249-522-2
• UNII: 5T206015T5
• DSSTox Substance ID: DTXSID40865478
• Nikkaji Number: J21.701H
• Wikipedia: Toloxatone
• Wikidata: Q3530618
• NCI Thesaurus Code: C97715
• Pharos Ligand ID: SXN6TSNX3S16
• Metabolomics Workbench ID: 144608
• ChEMBL ID: CHEMBL18116
• Mol file: 29218-27-7.mol

Synonyms:(3-methyl)-3-phenyl-5-hydroxymethyl-2-oxazolidinone;toloxatone

Chemical Property of Toloxatone

Chemical Property:

• Vapor Pressure: 8.9E-06mmHg at 25°C
• Melting Point: 76°
• Boiling Point: 358.9°Cat760mmHg
• Flash Point: 170.9°C
• Density: 1.245g/cm³
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 207.08954328
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

99% ^*data from raw suppliers

Toloxatone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)N2CC(OC2=O)CO
• Description: Toloxatone is a selective, reversible and competitive inhibitor of type A monoamine oxidase (MAO-A) which shows clinical utility as an antidepressant. It is reportedly free of the "cheese effect" in man, possibly due to the reversible nature of its inhibitory effect on intestinal MAO-A in the presence of high concentrations of tyramine.
• Uses: Toloxatone is a monoamine oxidase-A (MAO-A) inhibitor.

Technology Process of Toloxatone

There total 22 articles about Toloxatone 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%

5-(bromomethyl)-3-m-tolyloxazolidin-2-one → toloxatone (29218-27-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tet.2017.04.063

Reference yield: 82.0%

3-Iodotoluene (625-95-6) + 5-hydroxymethyl-2-oxazolidinone (7517-99-9) → toloxatone (29218-27-7) + 5-m-tolyloxymethyl-oxazolidin-2-one (57558-39-1)

Guidance literature:

With potassium phosphate; copper(l) iodide; (+/-)-trans-cyclohexanediamine; In 1,4-dioxane; at 110 ℃; for 24h;

DOI:10.3987/COM-03-S7

Reference yield: 79.0%

carbon dioxide (124-38-9,18923-20-1) + 3-methyl-N-(oxiran-2-ylmethyl)aniline → toloxatone (29218-27-7)

Guidance literature:

With dmap; C₂₀H₁₄AlNO₃; In dichloromethane; at 25 ℃; for 24h; under 760.051 Torr; Sealed tube;

DOI:10.1021/acs.orglett.8b02186

upstream raw materials:

3-(3-methyl-anilino)-propane-1,2-diol

Diethyl carbonate

3-{3-methylphenyl}-5-(tetrahydro-2H-2-pyranyloxy-methyl)-2-oxazolidinone

3-Iodotoluene

Downstream raw materials:

5-carbamoyloxymethyl-3-m-tolyl-oxazolidin-2-one

Refernces

• 1、 Bhunia, Subhajit,De, Subhadip,Ma, Dawei. "Room Temperature Cu-Catalyzed N-Arylation of Oxazolidinones and Amides with (Hetero)Aryl Iodides". supporting information. . Retrieved 2022/02/09.
• 2、 Rostami, Ali,Ebrahimi, Amirhossein,Husband, John,Anwar, Muhammad Usman,Csuk, Rene,Al-Harrasi, Ahmed. "Squaramide–Quaternary Ammonium Salt as an Effective Binary Organocatalytic System for Oxazolidinone Synthesis from Isocyanates and Epoxides". . p. 1881 - 1895. Retrieved 2020/03/13.