(E)-4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Pentadecafluoro-2-decenoic acid ethyl ester

Base Information

• Chemical Name: (E)-4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Pentadecafluoro-2-decenoic acid ethyl ester
• CAS No.: 37759-80-1
• Molecular Formula: C12H7F15O2
• Molecular Weight: 468.1588
• NSC Number: 146410
• DSSTox Substance ID: DTXSID201023285
• Nikkaji Number: J695.420K
• Mol file: 37759-80-1.mol

Synonyms:37759-80-1;NSC146410;DTXSID201023285;NSC-146410;(E)-4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Pentadecafluoro-2-decenoic acid ethyl ester;Ethyl (2E)-4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluorodec-2-enoate

Chemical Property of (E)-4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Pentadecafluoro-2-decenoic acid ethyl ester

Chemical Property:

• Vapor Pressure: 0.0709mmHg at 25°C
• Boiling Point: 229.1°Cat760mmHg
• Flash Point: 89.8°C
• Density: 1.531g/cm³
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 9
• Exact Mass: 468.0206519
• Heavy Atom Count: 29
• Complexity: 632

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F
• Isomeric SMILES: CCOC(=O)/C=C/C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F

Technology Process of (E)-4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Pentadecafluoro-2-decenoic acid ethyl ester

There total 5 articles about (E)-4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Pentadecafluoro-2-decenoic acid ethyl 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: 92.0%

Ethyl 3-F-heptyl 3-hydroxypropanoate (308-00-9,85571-86-4) → Ethyl E-3-F-heptyl 2-propenoate (37759-80-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform; for 24h; Heating;

DOI:10.1016/0022-1139(95)03297-Q

Reference yield: 56.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + ethyl perfluorooctanoate (3108-24-5) → Ethyl E-3-F-heptyl 2-propenoate (37759-80-1) + Ethyl Z-3-F-heptyl 2-propenoate (107124-83-4)

Guidance literature:

With n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; Yields of byproduct given; 1.) -78 deg C, 1 h, 2.) -78 deg C to r.t., 5 h;

DOI:10.1016/0022-1139(95)03297-Q

Reference yield:

pentadecafluoro-octanal (335-60-4) → Ethyl E-3-F-heptyl 2-propenoate (37759-80-1)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; toluene

2: hydrogen chloride

3: phosphorus (V)-oxide

With pyridine; hydrogenchloride; phosphorus pentoxide; toluene;

DOI:10.1021/ja01566a082

upstream raw materials:

Ethyl 3-F-heptyl 3-hydroxypropanoate

pentadecafluoro-octanal

diethyl malonate

diethoxyphosphoryl-acetic acid ethyl ester

Refernces

• 1、 Lanier,Haddach,Pastor,Riess. "Stereoselective synthesis of F-alkyl α,β-unsaturated esters and their epoxidation". . p. 2469 - 2472. Retrieved 2007/10/02.