Phenethyl methanesulfonate

Base Information

• Chemical Name: Phenethyl methanesulfonate
• CAS No.: 20020-27-3
• Molecular Formula: C9H12 O3 S
• Molecular Weight: 200.258
• Hs Code.: 2906299090
• DSSTox Substance ID: DTXSID00173844
• Nikkaji Number: J549.618G
• Wikidata: Q83043874
• Mol file: 20020-27-3.mol

Synonyms:Phenethyl methanesulfonate;20020-27-3;2-Phenylethyl methanesulfonate;Methanesulfonic acid, 2-phenylethyl ester;Phenethyl mesylate;2-Phenylethyl methanesulphonate;Methanesulfonic acid, phenethyl ester;BRN 2522079;methanesulfonic acid phenethyl ester;Phenethylmethanesulfonate;phenylethyl methansulfonate;SCHEMBL6589802;DTXSID00173844;MFCD01715258;AKOS022171938;DS-5379;LS-90345;CS-0150115;C73797

Chemical Property of Phenethyl methanesulfonate

Chemical Property:

• Vapor Pressure: 5.36E-05mmHg at 25°C
• Boiling Point: 358.1°Cat760mmHg
• Flash Point: 170.4°C
• PSA: 51.75000
• Density: 1.205g/cm³
• LogP: 2.28610
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 200.05071541
• Heavy Atom Count: 13
• Complexity: 222

Purity/Quality:

98% ^*data from raw suppliers

Phenethylmethanesulfonate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)OCCC1=CC=CC=C1

Technology Process of Phenethyl methanesulfonate

There total 2 articles about Phenethyl methanesulfonate 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: 99.0%

2-phenylethanol (60-12-8) + methanesulfonyl chloride (124-63-0) → 2-phenylethyl mesylate (20020-27-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.ejmech.2011.04.032

Reference yield:

phenylacetaldehyde (122-78-1) → 2-phenylethyl mesylate (20020-27-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate; methanol / 1 h / Cooling with ice

2: triethylamine / dichloromethane / 12 h / Cooling with ice

With methanol; sodium tetrahydroborate; triethylamine; In dichloromethane;

DOI:10.1016/j.bmc.2018.04.041

Reference yield: 98.0%

2-phenylethyl mesylate (20020-27-3) → 2-phenylethyl chloride (622-24-2)

Guidance literature:

With 1-butyl-3-methylimidazolium chloride; at 50 ℃; for 1h; Inert atmosphere; Green chemistry;

DOI:10.1055/s-0032-1317473 DOI:10.1055/s-0032-1317473

upstream raw materials:

2-phenylethanol

methanesulfonyl chloride

phenylacetaldehyde

Downstream raw materials:

ethyl dihydrocinnamate

(3-Benzyl-3H-imidazo[4,5-b]pyridin-2-yl)-(1-phenethyl-piperidin-4-yl)-amine

[3-(4-Fluoro-benzyl)-3H-imidazo[4,5-b]pyridin-2-yl]-(1-phenethyl-piperidin-4-yl)-amine

styrene

Refernces

• 1、 -. "Preparation method of mirabilone related substance and intermediate thereof". Paragraph 0078-0080. . Retrieved 2021/10/11.
• 2、 Lebel, Hélène,Mathieu, Gary,Patel, Heena. "Convenient Continuous Flow Synthesis of N-Methyl Secondary Amines from Alkyl Mesylates and Epoxides". supporting information. p. 2157 - 2168. Retrieved 2020/11/23.