Ethyl 4-nitrocinnamate

Base Information

• Chemical Name: Ethyl 4-nitrocinnamate
• CAS No.: 24393-61-1
• Molecular Formula: C11H11 N O4
• Molecular Weight: 221.213
• European Community (EC) Number: 213-463-0
• NSC Number: 636709,4697
• UNII: 25TMC6MV4P
• DSSTox Substance ID: DTXSID8061347,DTXSID601273204
• Nikkaji Number: J136.420K,J660.016F
• Wikidata: Q76119902
• ChEMBL ID: CHEMBL4102908
• Mol file: 24393-61-1.mol

Synonyms:Ethyl 4-nitrocinnamate;953-26-4;Ethyl p-nitrocinnamate;Ethyl 3-(4-nitrophenyl)acrylate;2-Propenoic acid, 3-(4-nitrophenyl)-, ethyl ester;24393-61-1;Cinnamic acid, p-nitro-, ethyl ester;ethyl (2E)-3-(4-nitrophenyl)acrylate;ethyl (E)-3-(4-nitrophenyl)prop-2-enoate;ETHYL4-NITROCINNAMATE;(E)-ethyl 3-(4-nitrophenyl)acrylate;Propenoic acid, 3-(4-nitrophenyl)-, ethyl ester;AI3-19857;NSC 4697;EINECS 213-463-0;BRN 2052533;NSC-4697;NSC636709;Ethyl 4-nitrocinnamate, predominantly trans;1-09-00-00247 (Beilstein Handbook Reference);C11H11NO4;4-Nitrocinnamic Acid Ethyl Ester;4-Nitrozimtsaeure-ethylester;Athyl-p-nitrocinnamat;ethyl4-nitrocinnnamate;Ethyl-4-nitrocinnamate;Ethyl (2E)-3-(4-nitrophenyl)-2-propenoate;ethyl (2E)-3-(4-nitrophenyl)prop-2-enoate;25TMC6MV4P;SCHEMBL275824;CHEMBL4102908;DTXSID8061347;NSC4697;DTXSID601273204;MFCD00007380;4-Nitrobenzeneacrylic acid ethyl ester;AKOS000278419;CS-W000345;MS-9824;NSC-636709;4-Nitro-trans-cinnamic acid ethyl ester;4-Nitrocinnamic acid ethyl ester, 98%;LS-54159;(E)-Ethyl 3-(4-nitrophenyl)prop-2-enoate;Ethyl (2E)-3-(4-nitrophenyl)-2-propenoate #;Ethyl 3-(4-(hydroxy(oxido)amino)phenyl)acrylate;A845277;AE-848/01504031;Ethyl 4-nitrocinnamate, predominantly trans, 99%;SR-01000025252;SR-01000025252-1;(E)-3-(4-nitrophenyl)-2-propenoic acid, ethyl ester;Z53861742

Chemical Property of Ethyl 4-nitrocinnamate

Chemical Property:

• Melting Point: 139-140℃
• Boiling Point: 326.6±17.0 °C(Predicted)
• PSA: 72.12000
• Density: 1.237±0.06 g/cm3(Predicted)
• LogP: 2.69430
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 221.06880783
• Heavy Atom Count: 16
• Complexity: 274

Purity/Quality:

99%, ^*data from raw suppliers

(E)-Ethyl 4-Nitrocinnamate >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC=C(C=C1)[N+](=O)[O-]
• Isomeric SMILES: CCOC(=O)/C=C/C1=CC=C(C=C1)[N+](=O)[O-]

Technology Process of Ethyl 4-nitrocinnamate

There total 79 articles about Ethyl 4-nitrocinnamate 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: 100.0%

4-nitrobenzaldehdye (555-16-8) + ethyl bromoacetate (105-36-2) → ethyl (E)-3-(4-nitrophenyl)-2-propenoate (24393-61-1)

Guidance literature:

With polyethyleneimine supported triphenylphosphine; In chloroform; at 65 ℃; Inert atmosphere;

DOI:10.1055/s-0034-1380810

Reference yield: 100.0%

para-nitrophenyl bromide (586-78-7) + ethyl acrylate (140-88-5,9003-32-1) → ethyl (E)-3-(4-nitrophenyl)-2-propenoate (24393-61-1)

Guidance literature:

With triethylamine; {[Pd(η⁵-C5H5)Fe(η⁵-C5H3)C(CH3)=N(C6H4CH3-4)](μ-I)}2; In 1,4-dioxane; at 100 ℃; for 10h;

DOI:10.1016/S0022-328X(01)00967-6

Reference yield: 100.0%

4-nitrobenzenediazonium tetrafluoroborate (456-27-9) + ethyl acrylate (140-88-5,9003-32-1) → ethyl (E)-3-(4-nitrophenyl)-2-propenoate (24393-61-1)

Guidance literature:

palladium diacetate; In ethanol; water; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2006.01.027

upstream raw materials:

ethyl 3-phenyl-2-propenoate

ethanol

4-nitro-trans-cinnamic acid

4-nitrobenzaldehdye

Downstream raw materials:

2-Isoquinolin-1-yl-4-(4-nitro-phenyl)-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

5-isoquinolin-1-yl-4-(4-nitro-phenyl)-2-phenyl-pyrrole-3-carboxylic acid ethyl ester

(4-Nitrophenyl)acetylene

2,3-dibromo-3-(4-nitro-phenyl)-propionic acid ethyl ester

Refernces

• 1、 Suárez-Escobedo, Laura,Gotor-Fernández, Vicente. "Solvent role in the lipase-catalysed esterification of cinnamic acid and derivatives. Optimisation of the biotransformation conditions". . . Retrieved 2021/02/05.
• 2、 Hong, Chang Whee,Lee, Yong Jin,An, Duk Keun. "A One-Pot Synthesis of α,β-Unsaturated Esters From Esters". . p. 1121 - 1125. Retrieved 2021/06/01.