(E)-Methyl-3-(4-fluorophenyl)acrylate

Base Information

• Chemical Name: (E)-Methyl-3-(4-fluorophenyl)acrylate
• CAS No.: 100891-10-9
• Molecular Formula: C₁₀H₉FO₂
• Molecular Weight: 180.179
• Mol file: 100891-10-9.mol

Synonyms:4-fluorocinnamic acid methyl ester;Methyl 4-fluorobenzoylacetate;methyl p-Fluorobenzoylacetate;methyl p-fluorocinnamate;(E)-METHYL 3-(4-FLUOROPHENYL)ACRYLATE;(E)-METHYL-3-(4-FLUOROPHENYL)ACRYLATE;methyl trans-4-fluorocinnamate;

Chemical Property of (E)-Methyl-3-(4-fluorophenyl)acrylate

Chemical Property:

• Melting Point: 45-47 °C
• Boiling Point: 130-133 °C(Press: 15 Torr)
• PSA: 26.30000
• Density: 1.165±0.06 g/cm3(Predicted)
• LogP: 2.01190

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 3-(4-fluorophenyl)acrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (E)-Methyl-3-(4-fluorophenyl)acrylate

There total 51 articles about (E)-Methyl-3-(4-fluorophenyl)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: 99.0%

methanol (67-56-1) + 4-fluorocinnamic acid (459-32-5,14290-66-5,14290-86-9) → methyl p-fluorocinnamate (100891-10-9,96426-60-7)

Guidance literature:

With thionyl chloride; at 20 ℃; for 18h;

DOI:10.1016/S0957-4166(01)00069-6

Reference yield: 95.0%

methanol (67-56-1) + (E)-4-fluorocinnamic acid (459-32-5) → methyl (2E)-3-(4-fluorophenyl)-2-propenoate (96426-60-7,100891-10-9)

Guidance literature:

With sulfuric acid; for 2h; Heating;

DOI:10.1016/S0968-0896(97)10017-7

Reference yield: 95.0%

4-fluoro-1-iodobenzene (352-34-1) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl (2E)-3-(4-fluorophenyl)-2-propenoate (96426-60-7,100891-10-9)

Guidance literature:

With {1-[3-(MeO)3Si(CH₂)3]-3-Me-4-imidazolin-2-yl}2PdCl₂; sodium acetate; In 1-methyl-pyrrolidin-2-one; at 140 ℃; for 4h;

DOI:10.1021/ol060129z

upstream raw materials:

4-fluorobenzaldehyde

bromoacetic acid methyl ester

methanol

4-fluorocinnamic acid

Downstream raw materials:

(E)-3-(4-fluorophenyl)-2-propen-1-ol

3-(4-Fluorophenyl)propionic acid,methyl ester

Refernces

• 1、 Wang, Gang,Xu, Yiming,Zhang, Suojiang,Li, Zengxi,Li, Chunshan. "An ionic liquid catalyzed probase method for one-pot synthesis of α,β-unsaturated esters from esters and aldehydes under mild conditions". . p. 4838 - 4848. Retrieved 2017.
• 2、 Dhudshia, Bhartesh,Thadani, Avinash N.. "Acyclic diaminocarbenes: Simple, versatile ligands for cross-coupling reactions". . p. 668 - 670. Retrieved 2006.
• 3、 Burmaoglu, Serdar,Yilmaz, Ali O.,Taslimi, Parham,Algul, Oztekin,Kilic, Deryanur,Gulcin, Ilhami. "Synthesis and biological evaluation of phloroglucinol derivatives possessing α-glycosidase, acetylcholinesterase, butyrylcholinesterase, carbonic anhydrase inhibitory activity". . . Retrieved 2018.
• 4、 Smith, James M.,Greaney, Michael F.. "A one-pot silyl-Reformatsky olefination". . p. 8687 - 8690. Retrieved 2007.
• 5、 Zheng,Shen. "Cadmium-catalyzed olefination of aldehydes with α-bromoacetic ester in the presence of tri-n-butylarsine". . p. 2069 - 2073. Retrieved 1994.
• 6、 Churruca, Fátima,SanMartin, Raul,Tellitu, Imanol,Domínguez, Esther. "N-heterocyclic NCN-pincer palladium complexes: A source for general, highly efficient catalysts in Heck, Suzuki, and Sonogashira coupling reactions". . p. 3116 - 3120. Retrieved 2005.
• 7、 Shen, Yanchang,Yang, Baozheng,Yuan, Gang. "Novel Conversion of Aldehydes to Alkenes Mediated by Tri-n-butylarsine and Zinc". . p. 144. Retrieved 1989.
• 8、 Moyna, Guillermo,Williams, Howard J.,Scott. "An improved procedure for the epoxidation of methyl cinnamate derivatives and production of acid sensitive epoxides". . p. 2235 - 2239. Retrieved 1996.
• 9、 Shore, Gjergji,Morin, Sylvie,Organ, Michael G.. "Catalysis in capillaries by Pd thin films using Microwave-Assisted Continuous-flow Organic Synthesis (MACOS)". . p. 2761 - 2766. Retrieved 2006.
• 10、 Zeng, Minfeng,Zhang, Xin,Shao, Linjun,Qi, Chenze,Zhang, Xian-Man. "Highly porous chitosan microspheres supported palladium catalyst for coupling reactions in organic and aqueous solutions". . p. 29 - 37. Retrieved 2012.