Ethyl 3-(3,5-difluorophenyl)acrylate

Base Information

• Chemical Name: Ethyl 3-(3,5-difluorophenyl)acrylate
• CAS No.: 163978-50-5
• Molecular Formula: C11H10 F2 O2
• Molecular Weight: 212.19
• DSSTox Substance ID: DTXSID90457246
• Nikkaji Number: J2.200.583I
• Wikidata: Q82280018
• Mol file: 163978-50-5.mol

Synonyms:Ethyl 3-(3,5-difluorophenyl)acrylate;163978-50-5;861631-72-3;Ethyl (E)-3-(3,5-difluorophenyl)prop-2-enoate;Ethyl (E)-3-(3,5-difluorophenyl)acrylate;2-Propenoic acid, 3-(3,5-difluorophenyl)-, ethyl ester;ethyl (E)-3-(35-difluorophenyl)acrylate;starbld0014227;Ethyl 3 5difluorocinnamate;SCHEMBL534282;DTXSID90457246;ETHYL 3?5?DIFLUOROCINNAMATE;MFCD03095009;AKOS015891004;CS-0347721;EN300-1453851;ETHYL 3-(3,5-DIFLUOROPHENYL)PROP-2-ENOATE;(E)-3-(3,5-Difluorophenyl)propenoic acid ethyl ester;(E)-3-(3,5-Difluoro-phenyl)-acrylic acid ethyl ester;ETHYL (2E)-3-(3,5-DIFLUOROPHENYL)PROP-2-ENOATE

Chemical Property of Ethyl 3-(3,5-difluorophenyl)acrylate

Chemical Property:

• Vapor Pressure: 0.0109mmHg at 25°C
• Refractive Index: 1.518
• Boiling Point: 262.4°Cat760mmHg
• Flash Point: 109.2°C
• PSA: 26.30000
• Density: 1.21g/cm³
• LogP: 2.54110
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 212.06488588
• Heavy Atom Count: 15
• Complexity: 231

Purity/Quality:

Ethyl3-(3,5-difluorophenyl)acrylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC(=CC(=C1)F)F
• Isomeric SMILES: CCOC(=O)/C=C/C1=CC(=CC(=C1)F)F

Technology Process of Ethyl 3-(3,5-difluorophenyl)acrylate

There total 2 articles about Ethyl 3-(3,5-difluorophenyl)acrylate 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: 89.0%

3,5-difluorobenzaldehyde (32085-88-4) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl 3-(3,5-difluorophenyl)acrylate (163978-50-5)

Guidance literature:

In tetrahydrofuran; dichloromethane; at 0 - 5 ℃; for 1h;

DOI:10.1021/acschemneuro.8b00526

Reference yield:

1,3-Difluorobenzene (372-18-9) + ethyl acrylate (140-88-5,9003-32-1) → C11H10F2O2 + C11H10F2O2 + ethyl 3-(3,5-difluorophenyl)acrylate (163978-50-5)

Guidance literature:

With 3,5-bis(trifluoromethyl)pyridin-2(1H)-one; silver(I) acetate; palladium diacetate; at 100 ℃; for 24h; Overall yield = 50 %; regioselective reaction; Sealed tube;

DOI:10.1038/nature24632

Reference yield: 100.0%

nitromethane (75-52-5) + ethyl 3-(3,5-difluorophenyl)acrylate (163978-50-5) → ethyl 3-(3,5-difluorophenyl)-4-nitrobutanoate

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at -20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acschemneuro.8b00526

upstream raw materials:

3,5-difluorobenzaldehyde

ethyl (triphenylphosphoranylidene)acetate

1,3-Difluorobenzene

ethyl acrylate

Downstream raw materials:

ethyl 3-(3,5-difluorophenyl)propionate

5-(3,5-Difluoro-benzyl)-1H-pyrimidine-2,4-dione

5-(3,5-Difluoro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

Acetic acid 2-[5-(3,5-difluoro-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy]-ethyl ester

Refernces

• 1、 Wang, Peng,Verma, Pritha,Xia, Guoqin,Shi, Jun,Qiao, Jennifer X.,Tao, Shiwei,Cheng, Peter T. W.,Poss, Michael A.,Farmer, Marcus E.,Yeung, Kap-Sun,Yu, Jin-Quan. "Ligand-accelerated non-directed C-H functionalization of arenes". . p. 489 - 493. Retrieved 2017/11/28.