Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate

Base Information

• Chemical Name: Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate
• CAS No.: 42245-42-1
• Molecular Formula: C11H12O4
• Molecular Weight: 208.214
• European Community (EC) Number: 404-130-2,255-735-1
• DSSTox Substance ID: DTXSID90885863
• Nikkaji Number: J241.507K
• Mol file: 42245-42-1.mol

Synonyms:3-(-methoxyphenyl)glycidic acid methylester;methyl (2R,3S)-3-(4-methoxyphenyl)glycidate;methyl 2,3-epoxy-3-(4-methoxyphenyl)propionate;methyl 3-(4-methoxyphenyl)glycidate;methyl-3-(4-methoxyphenyl)glycidate;t-methyl-3-phenylglycidate

Chemical Property of Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.00133mmHg at 25°C
• Melting Point: 69-71 °C(lit.)
• Refractive Index: 1.534
• Boiling Point: 297.7 °C at 760 mmHg
• Flash Point: 129.2 °C
• PSA: 48.06000
• Density: 1.224 g/cm³
• LogP: 1.30810
• Solubility.: Dichloromethane; Chloroform; Ethyl Acetate; DMSO
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 208.07355886
• Heavy Atom Count: 15
• Complexity: 233

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl trans-3-(4-methoxyphenyl)glycidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2C(O2)C(=O)OC
• Description: Methyl 2,3 epoXY-3-(4-methoxyphenyl)propionate is an intermediate product in the synthesis of diltiazem hydrochloride. Contact dermatitis was observed in several laboratory technicians.
• Uses: Methyl trans-3-(4-Methoxyphenyl)glycidate is an intermediate used in the synthesis of Clentiazem (C573035), which is a benzothiazepine-like calcium antagonists; Enhances endothelium-dependent coronary artery relaxation.

Technology Process of Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate

There total 13 articles about Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate 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: 95.0%

methyl (2-RS,3-SR)-3-hydroxy-3-(4-methoxyphenyl)-2-<(4-methoxyphenyl)sulfonyloxy>propanoate → methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate (42245-42-1,84056-02-0,84976-49-8,88877-35-4,96125-49-4,105560-93-8,126060-70-6,134931-64-9,137173-40-1)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; for 1h; Ambient temperature;

Reference yield: 88.4%

4-methoxy-benzaldehyde (123-11-5) + methyl chloroacetate (96-34-4) → methyl 3-(4-methoxyphenyl)glycidate (42245-42-1)

Guidance literature:

With sodium methylate; In ethanol; at 5 - 35 ℃; for 2h;

Reference yield: 17.1%

4-methoxy-benzaldehyde (123-11-5) + methyl chloroacetate (96-34-4) → methyl trans-3-(4-methoxyphenyl)glycidate (96125-49-4) + methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate (42245-42-1,84056-02-0,84976-49-8,88877-35-4,96125-49-4,105560-93-8,126060-70-6,134931-64-9,137173-40-1)

Guidance literature:

With sodium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide; Ambient temperature;

upstream raw materials:

4-methoxy-benzaldehyde

methyl chloroacetate

3-(4-methoxy-phenyl)acrylic acid methyl ester

3-chloro-benzenecarboperoxoic acid

Downstream raw materials:

3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

(+/-)-trans-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester

methyl threo-2-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionate

Refernces

• 1、 -. "Preparation and purification method of diltiazem chiral isomer impurity". Paragraph 0017-0018. . Retrieved 2019/11/20.
• 2、 Yang, Xiaodong,Yang, Shenghua,Xiang, Likui,Pang, Xiaobo,Chen, Baohua,Huang, Guosheng,Yan, Rulong. "Synthesis of 3-Arylpyridines via Palladium/Copper-Catalyzed Annulation of Allylamine/1,3-Propanediamine and Aldehydes". supporting information. p. 3732 - 3736. Retrieved 2016/01/25.