(S)-2-((3-NITROPHENOXY)METHYL)OXIRANE

Base Information

• Chemical Name: (S)-2-((3-NITROPHENOXY)METHYL)OXIRANE
• CAS No.: 171721-34-9
• Molecular Formula: C9H9NO4
• Molecular Weight: 195.175
• Mol file: 171721-34-9.mol

Synonyms:(S)-2-((3-NITROPHENOXY)METHYL)OXIRANE

Chemical Property of (S)-2-((3-NITROPHENOXY)METHYL)OXIRANE

Chemical Property:

• Melting Point: 63.0-64.2 °C
• Boiling Point: 342.6±12.0 °C(Predicted)
• PSA: 67.58000
• Density: 1.340±0.06 g/cm3(Predicted)
• LogP: 1.89560

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((3-NITROPHENOXY)METHYL)OXIRANE

There total 3 articles about (S)-2-((3-NITROPHENOXY)METHYL)OXIRANE 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: 80.0%

meta-nitrophenol (554-84-7) + (2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) → (S)-1,2-epoxy-3-(3-nitrophenoxy)propane (171721-34-9)

Guidance literature:

meta-nitrophenol; With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

(2s)-(+)-glycidyl 3-nitrobenzenesulfonate; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1021/jm8002153

Reference yield: 45.0%

Glycidyl m-nitrophenyl ether (5332-66-1) → (S)-1,2-epoxy-3-(3-nitrophenoxy)propane (171721-34-9) + rac-3-(3-nitrophenoxy)-1,2-propanediol (63991-99-1)

Guidance literature:

With Bacillus megaterium ECU₁₀₀₁ epoxide hydrolase; In potassium phosphate buffer; dimethyl sulfoxide; at 30 ℃; for 0.5h; pH=7; optical yield given as %ee; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1002/adsc.201100031

Reference yield:

meta-nitrophenol (554-84-7) → (S)-1,2-epoxy-3-(3-nitrophenoxy)propane (171721-34-9) + rac-3-(3-nitrophenoxy)-1,2-propanediol (63991-99-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water / 5 h / 20 °C

2: Bacillus megaterium ECU₁₀₀₁ epoxide hydrolase / potassium phosphate buffer; dimethyl sulfoxide / 0.5 h / 30 °C / pH 7 / Resolution of racemate; Enzymatic reaction

With Bacillus megaterium ECU₁₀₀₁ epoxide hydrolase; sodium hydroxide; In potassium phosphate buffer; water; dimethyl sulfoxide;

DOI:10.1002/adsc.201100031

upstream raw materials:

meta-nitrophenol

(2s)-(+)-glycidyl 3-nitrobenzenesulfonate

Glycidyl m-nitrophenyl ether

Downstream raw materials:

(S)-glycidyl 3-aminophenyl ether

Refernces

• 1、 Tahirovic, Yesim A.,Geballe, Matthew,Gruszecka-Kowalik, Ewa,Myers, Scott J.,Lyuboslavsky, Polina,Le, Phuong,French, Adam,Irier, Hasan,Choi, Woo-Baeg,Easterling, Keith,Yuan, Hongjie,Wilson, Lawrence J.,Kotloski, Robert,McNamara, James O.,Dingledine, Raymond,Liotta, Dennis C.,Traynelis, Stephen F.,Snyder, James P.. "Enantiomeric propanolamines as selective N-methyl-D-aspartate 2B receptor antagonists". supporting information; experimental part. p. 5506 - 5521. Retrieved 2009/08/07.