Methyl (E)-m-nitrocinnamate

Base Information

• Chemical Name: Methyl (E)-m-nitrocinnamate
• CAS No.: 1664-59-1
• Molecular Formula: C10H9 N O4
• Molecular Weight: 207.186
• European Community (EC) Number: 211-529-3
• NSC Number: 1322
• DSSTox Substance ID: DTXSID701267210
• Nikkaji Number: J95.046G
• ChEMBL ID: CHEMBL1774695
• Mol file: 1664-59-1.mol

Synonyms:659-04-1;(E)-methyl 3-(3-nitrophenyl)acrylate;1664-59-1;Methyl (E)-m-nitrocinnamate;3-(3-Nitro-phenyl)-acrylic acid methyl ester;3-(3-Nitrophenyl)acrylic acid methyl ester;methyl (E)-3-(3-nitrophenyl)prop-2-enoate;Methyl (E)-3-(3-nitrophenyl)acrylate;2-Propenoic acid, 3-(3-nitrophenyl)-, methyl ester;methyl (2E)-3-(3-nitrophenyl)prop-2-enoate;EINECS 211-529-3;Methyl (E)-3-(3-nitrophenyl)-2-propenoate;3-Nitrocinnamic acid methyl ester;MFCD00024570;M-nitro cinnamic acid, methyl ester;Methyl 3-nitro-cinnamate;METHYL 3-NITROCINNAMATE;SCHEMBL1284478;CHEMBL1774695;AMY4848;NSC1322;Methyl 3-(3-nitrophenyl)acrylate;2-Propenoic acid, 3-(3-nitrophenyl)-, methyl ester, (2E)-;DTXSID701267210;NSC 1322;NSC-1322;BBL100148;STL406968;(E)-methyl3-(3-nitrophenyl)acrylate;AKOS005259822;CS-W020528;Methyl (2E)-3-(3-nitrophenyl)acrylate;CS-13374;Methyl (2E)-3-(3-nitrophenyl)-2-propenoate;W11273;Methyl (2E)-3-(3-nitrophenyl)-2-propenoate #;(E)-3-(3-nitrophenyl)-acrylic acid methyl ester;3-(M-NITROPHENYL)-2-PROPENOIC ACID, METHYL ESTER

Chemical Property of Methyl (E)-m-nitrocinnamate

Chemical Property:

• Melting Point: 120 °C
• Boiling Point: 334°Cat760mmHg
• Flash Point: 154.8°C
• PSA: 72.12000
• Density: 1.277g/cm³
• LogP: 2.30420
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 207.05315777
• Heavy Atom Count: 15
• Complexity: 269

Purity/Quality:

METHYL 3-NITROCINNAMATE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl (E)-m-nitrocinnamate

There total 13 articles about Methyl (E)-m-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: 99.0%

m-iodonitrobenzene (645-00-1) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 3-(3-nitrophenyl)acrylic acid methyl ester (1664-59-1)

Guidance literature:

With tributyl-amine; In dodecane; at 120 ℃; for 3h;

DOI:10.1055/s-0028-1087488

Reference yield: 97.0%

Methyl diethylphosphonoacetate (1067-74-9) + 3-nitro-benzaldehyde (99-61-6) → 3-(3-nitrophenyl)acrylic acid methyl ester (1664-59-1)

Guidance literature:

Methyl diethylphosphonoacetate; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

3-nitro-benzaldehyde; In tetrahydrofuran; hexane; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00915

Reference yield: 94.0%

methanol (67-56-1) + m-Nitrocinnamic Acid (555-68-0,1772-76-5) → 3-(3-nitrophenyl)acrylic acid methyl ester (1664-59-1)

Guidance literature:

With sulfuric acid; for 24h; Reflux;

upstream raw materials:

piperidine

pyridine

Malonic acid monomethyl ester

3-nitro-benzaldehyde

Downstream raw materials:

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

methyl 3-aminocinnamate

methyl 3-(3-nitrophenyl)propanoate

4-nitro-3-(3-nitrophenyl)butyric acid methyl ester