Methyl (4-nitrophenoxy)acetate

Base Information

• Chemical Name: Methyl (4-nitrophenoxy)acetate
• CAS No.: 19786-48-2
• Molecular Formula: C9H9NO5
• Molecular Weight: 211.174
• DSSTox Substance ID: DTXSID00351448
• Nikkaji Number: J47.489D
• Wikidata: Q63396644
• Mol file: 19786-48-2.mol

Synonyms:methyl (4-nitrophenoxy)acetate;19786-48-2;methyl 2-(4-nitrophenoxy)acetate;(4-Nitrophenoxy)acetic acid methyl ester;4-Nitrophenoxyacetic acid methyl ester;Methyl 4-nitrophenoxyacetate;Oprea1_145451;methyl 4-nitro-phenoxyacetate;SCHEMBL839776;Methyl(4-Nitro phenoxy)acetate;methyl2-(4-nitrophenoxy)acetate;Methyl (4-Nitro phenoxy)acetate;DTXSID00351448;ZZVXTAUUUUCLAG-UHFFFAOYSA-N;MFCD01035955;STK047130;4-Methoxycarbonylmethyloxy-nitrobenzene;AKOS000489145;LS-07581;(4-Nitro-phenoxy)-acetic acid methyl ester;SR-01000405611;SR-01000405611-1;Q63396644

Chemical Property of Methyl (4-nitrophenoxy)acetate

Chemical Property:

• Melting Point: 99 °C
• Boiling Point: 337.4±17.0 °C(Predicted)
• PSA: 81.35000
• Density: 1.305±0.06 g/cm3(Predicted)
• LogP: 1.66980
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 211.04807239
• Heavy Atom Count: 15
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

Methyl4-Nitrophenoxyacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)COC1=CC=C(C=C1)[N+](=O)[O-]
• Uses: Methyl 4-Nitrophenoxyacetate is an intermediate in synthesizing 2-(4-(Methylsulfonamido)phenoxy)acetic Acid-13C (M332217), an isotopically labelled analogue of 2-(4-(Methylsulfonamido)phenoxy)acetic Acid (M332215), which is a metabolite of antiarrhythmic drug Dofetilide (D525700), a potassium channel blocker.

Technology Process of Methyl (4-nitrophenoxy)acetate

There total 8 articles about Methyl (4-nitrophenoxy)acetate 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: 96.0%

4-nitrophenoxyacetic acid (1798-11-4) → methyl 2-(4-nitrophenoxy)acetate (19786-48-2)

Guidance literature:

With thionyl chloride; sodium chloride; sodium hydrogencarbonate; In methanol; dichloromethane;

Reference yield: 95.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + methyl chloroacetate (96-34-4) → methyl 2-(4-nitrophenoxy)acetate (19786-48-2)

Guidance literature:

With polyethylene glycol-600; potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; for 0.0666667h; microwave irradiation;

DOI:10.1081/SCC-200063928

Reference yield: 95.0%

methanol (67-56-1) + 4-nitrophenoxyacetic acid (1798-11-4) → methyl 2-(4-nitrophenoxy)acetate (19786-48-2)

Guidance literature:

methanol; With thionyl chloride; at -10 ℃; for 0.166667h;

4-nitrophenoxyacetic acid; for 1h;

DOI:10.1016/j.bmc.2009.05.085

upstream raw materials:

methanol

2-(4-nitrophenoxy)acetyl chloride

4-nitrophenoxyacetic acid

4-nitro-phenol

Downstream raw materials:

4-nitrophenoxyacetic acid

ethyl 2-(4-aminophenoxy)acetate

C₂₄H₂₆FN₃O₃

C₂₅H₂₆FN₃O₄

Refernces

• 1、 Liosi, Maria-Elena,Krimmer, Stefan G.,Newton, Ana S.,Dawson, Thomas K.,Puleo, David E.,Cutrona, Kara J.,Suzuki, Yoshihisa,Schlessinger, Joseph,Jorgensen, William L.. "Selective Janus Kinase 2 (JAK2) Pseudokinase Ligands with a Diaminotriazole Core". . p. 5324 - 5340. Retrieved 2020/06/10.
• 2、 Zidar, Nace,Macut, Helena,Toma?i?, Tihomir,Peterlin Ma?i?, Lucija,Ila?, Janez,Zega, Anamarija,Tammela, P?ivi,Kikelj, Danijel. "New: N -phenyl-4,5-dibromopyrrolamides as DNA gyrase B inhibitors". supporting information. p. 1007 - 1017. Retrieved 2019/06/27.