4-(N,N-Diethylamino)cinnamic acid

Base Information

• Chemical Name: 4-(N,N-Diethylamino)cinnamic acid
• CAS No.: 1552-97-2
• Molecular Formula: C13H17 N O2
• Molecular Weight: 219.283
• Hs Code.: 2922499990
• Mol file: 1552-97-2.mol

Synonyms:Cinnamicacid, p-(dimethylamino)-, ethyl ester (6CI,7CI,8CI);3-[4-(Dimethylamino)phenyl]-2-propenoic acid ethyl ester; Ethyl4-(dimethylamino)cinnamate; Ethyl p-dimethylaminocinnamate; NSC 636697

Chemical Property of 4-(N,N-Diethylamino)cinnamic acid

Chemical Property:

• Melting Point: 74-75 °C
• Boiling Point: 205-208 °C(Press: 19 Torr)
• PKA: 3.03±0.12(Predicted)
• PSA: 40.54000
• Density: 1.070±0.06 g/cm3(Predicted)
• LogP: 2.63060

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-(N,N-Diethylamino)cinnamic acid

There total 28 articles about 4-(N,N-Diethylamino)cinnamic acid 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: 98.0%

4-bromo-N,N-dimethylaniline (586-77-6) + ethyl acrylate (140-88-5,9003-32-1) → 3-[4-(dimethylamino)phenyl]-2-propenoic acid ethyl ester (1552-97-2)

Guidance literature:

With potassium phosphate; [((ferrocenyl)(C(CH₃)N(C₆H₄)CH₃))PdCl(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)]; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 140 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.tet.2010.04.040

Reference yield: 95.0%

diazoacetic acid ethyl ester (623-73-4) + 4-dimethylamino-benzaldehyde (100-10-7) → ethyl (E)-3-(4-(dimethylamino)phenyl)acrylate (1552-97-2,39806-13-8)

Guidance literature:

With triphenylphosphine; ruthenium-salen complex; In toluene; at 100 ℃; for 24h;

DOI:10.1016/j.tetlet.2006.01.055

Reference yield: 95.0%

diazoacetic acid ethyl ester (623-73-4) + 4-dimethylamino-benzaldehyde (100-10-7) → 3-[4-(dimethylamino)phenyl]-2-propenoic acid ethyl ester (1552-97-2)

Guidance literature:

With triphenylphosphine; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; meso-tetrakis(tetraphenyl)porphyrin iron(III) chloride; In dichloromethane; at 80 ℃; for 20h;

DOI:10.1016/j.tetlet.2004.08.070

upstream raw materials:

ethyl acetate

4-dimethylamino-benzaldehyde

ethyl bromoacetate

hydrogen ethyl malonate

Downstream raw materials:

(E)-3-{4-(N,N-dimethylamino)phenyl}prop-2-en-1-ol

3-(4-dimethylaminophenyl)-prop-2-en-1-ol

p-dimethylaminocinnamic acid

(E)-4-(4-dimethylaminostyryl)-1,6-heptadien-4-ol

Refernces

• 1、 Bezerra Fran?a, Saraliny,Carine Barros de Lima, Luana,Rychard da Silva Cunha, Cristhyan,Santos Anuncia??o, Daniela,Ferreira da Silva-Júnior, Edeildo,Ester de Sá Barreto Barros, Maria,José da Paz Lima, Dimas. "Larvicidal activity and in silico studies of cinnamic acid derivatives against Aedes aegypti (Diptera: Culicidae)". . . Retrieved 2021/07/07.
• 2、 Bernal, Freddy A.,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.. "Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents". . p. 68 - 78. Retrieved 2019/11/22.