Benzenepropanoic acid, 4-(oxiranylmethoxy)-, methyl ester

Base Information

• Chemical Name: Benzenepropanoic acid, 4-(oxiranylmethoxy)-, methyl ester
• CAS No.: 81147-94-6
• Molecular Formula: C13H16 O4
• Molecular Weight: 236.268
• UNII: VW39QXX4G7
• DSSTox Substance ID: DTXSID00868602
• Nikkaji Number: J705.296K
• Mol file: 81147-94-6.mol

Synonyms:81147-94-6;Benzenepropanoic acid, 4-(oxiranylmethoxy)-, methyl ester;METHYL 3-[4-(OXIRAN-2-YLMETHOXY)PHENYL]PROPANOATE;BENZENEPROPANOICACID,4-(OXIRANYLMETHOXY)-,METHYLESTER;3-(4-(2,3-Epoxypropoxy)phenyl)propionic acid methyl ester;Methyl 3[4-(2,3-Epoxypropoxy)phenyl]propionate;VW39QXX4G7;SCHEMBL1041018;DTXSID00868602;BDCUIFGTTIEBLT-UHFFFAOYSA-N;MFCD23102977;FT-0673348;Methyl 4-(2-oxiranylmethoxy)benzenepropanoate;methyl 3-[4-(2,3-epoxypropoxy)phenyl]propionate;Methyl 3-{4-[(oxiran-2-yl)methoxy]phenyl}propanoate;3-(4-Oxiranylmethoxy-phenyl)-propionic acid methyl ester;Benzenepropanoic acid, 4-(2-oxiranylmethoxy)-, methyl ester

Chemical Property of Benzenepropanoic acid, 4-(oxiranylmethoxy)-, methyl ester

Chemical Property:

• Boiling Point: 156 °C(Press: 0.4 Torr)
• PSA: 48.06000
• Density: 1.163±0.06 g/cm3(Predicted)
• LogP: 1.56980
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 236.10485899
• Heavy Atom Count: 17
• Complexity: 246

Purity/Quality:

95% ^*data from raw suppliers

3-(4-(2,3-Epoxypropoxy)phenyl)propionicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC1=CC=C(C=C1)OCC2CO2
• Uses: 3-(4-(2,3-Epoxypropoxy)phenyl)propionic Acid Methyl Ester is an intermediate in the synthesis of N-Ethyl Esmolol (E918045), which is an impurity of esmolol (E668000), which is a cardioselective β-adrenergic blocker. Antiarrhythmic.

Technology Process of Benzenepropanoic acid, 4-(oxiranylmethoxy)-, methyl ester

There total 9 articles about Benzenepropanoic acid, 4-(oxiranylmethoxy)-, methyl ester 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: 97.9%

3-(4-hydroxyphenyl)propionic acid methyl ester (5597-50-2) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → methyl 3-<4-(2,3-epoxypropoxy)phenyl>propionate (81147-94-6,246219-23-8)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In tetrahydrofuran; at 60 - 65 ℃;

Reference yield: 86.0%

3-(4-hydroxyphenyl)propionic acid methyl ester (5597-50-2) + 1,2-Epoxy-3-bromopropane (3132-64-7,82584-73-4) → methyl 3-<4-(2,3-epoxypropoxy)phenyl>propionate (81147-94-6,246219-23-8)

Guidance literature:

With potassium carbonate; In butanone; for 8h; Heating;

DOI:10.1002/ardp.200400920

Reference yield:

3-(4-hydroxyphenyl)propionic acid methyl ester (5597-50-2) + potassium carbonate (584-08-7) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → methyl 3-<4-(2,3-epoxypropoxy)phenyl>propionate (81147-94-6,246219-23-8)

Guidance literature:

With sodium hydroxide; In water; acetone; toluene;

upstream raw materials:

glycidyl p-toluenesulfonate

3-(4-hydroxyphenyl)propionic acid methyl ester

epichlorohydrin

1,2-Epoxy-3-bromopropane

Downstream raw materials:

3-{4-[3-(1,1-Dimethyl-2-ureido-ethylamino)-2-hydroxy-propoxy]-phenyl}-propionic acid methyl ester

ethyl 3-[N-[2-hydroxy-3-[4-[2-(methoxycarbonyl)ethyl]phenoxy]propyl]amino]propionate hydrochloride

methyl (S)-3-[4-(oxiran-2-ylmethoxy)phenyl]propanoate

methyl (S)-3-[4-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl]propanoate

Refernces

• 1、 -. "Preparation process of high-purity iprolol hydrochloride". Paragraph 0031; 0032. . Retrieved 2021/11/19.
• 2、 Schmitt, Martin L.,Hauser, Alexander-Thomas,Carlino, Luca,Pippel, Martin,Schulz-Fincke, Johannes,Metzger, Eric,Willmann, Dominica,Yiu, Teresa,Barton, Michelle,Schüle, Roland,Sippl, Wolfgang,Jung, Manfred. "Nonpeptidic propargylamines as inhibitors of lysine specific demethylase 1 (LSD1) with cellular activity". supporting information. p. 7334 - 7342. Retrieved 2013/10/21.