2-Methoxy-5-nitrocinnamic acid

Base Information

• Chemical Name: 2-Methoxy-5-nitrocinnamic acid
• CAS No.: 69447-75-2
• Molecular Formula: C10H9 N O5
• Molecular Weight: 223.185
• DSSTox Substance ID: DTXSID8071984
• Nikkaji Number: J441.309A
• Wikidata: Q76386494
• Mol file: 69447-75-2.mol

Synonyms:2-Methoxy-5-nitrocinnamic acid;288151-91-7;69447-75-2;(E)-3-(2-methoxy-5-nitrophenyl)prop-2-enoic acid;(2E)-3-(2-methoxy-5-nitrophenyl)prop-2-enoic acid;2-Propenoic acid, 3-(2-methoxy-5-nitrophenyl)-;(E)-3-(2-methoxy-5-nitrophenyl)-2-propenoic acid;SCHEMBL6588014;SCHEMBL6588022;DTXSID8071984;BBL036207;STK398136;AKOS000304689;VS-13367;3-(2-Methoxy-5-nitrophenyl)propenoic acid;3-(2-methoxy-5-nitrophenyl)prop-2-enoic acid;EN300-1854520;(E)-3-(2-Methoxy-5-nitro-phenyl)-acrylic acid;(E)-3-(2-methoxy-5-nitro-phenyl)prop-2-enoicacid;(E)-3-(2-methoxy-5-nitro-phenyl)prop-2-enoic acid

Chemical Property of 2-Methoxy-5-nitrocinnamic acid

Chemical Property:

• Vapor Pressure: 4.94E-08mmHg at 25°C
• Boiling Point: 426.5°C at 760 mmHg
• Flash Point: 211.7°C
• PSA: 92.35000
• Density: 1.387g/cm³
• LogP: 2.22440
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 223.04807239
• Heavy Atom Count: 16
• Complexity: 296

Purity/Quality:

2-Methoxy-5-nitrocinnamicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)[N+](=O)[O-])C=CC(=O)O
• Isomeric SMILES: COC1=C(C=C(C=C1)[N+](=O)[O-])/C=C/C(=O)O

Technology Process of 2-Methoxy-5-nitrocinnamic acid

There total 11 articles about 2-Methoxy-5-nitrocinnamic 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: 20.0%

2-methoxycinnamic acid (1011-54-7) → 2-methoxy-5-nitrobenzaldehyde (25016-02-8) + 5-nitro-2-methoxy-trans-cinnamic acid (69447-75-2,288151-91-7) + (E)-1-methoxy-4-nitro-2-(2-nitroethenyl)benzene (118510-00-2) + (E)-2-methoxy-1-nitro-3-(2-nitroethenyl)benzene (118509-99-2)

Guidance literature:

With ammonium cerium(IV) nitrate; trifluoroacetic acid; at 23 ℃; for 1h; Yields of byproduct given;

Reference yield:

sulfuric acid (7664-93-9) + 5-nitro-2-methoxy-cis-cinnamic acid (69447-75-2,288151-91-7) → 6-nitrocoumarin (2725-81-7) + 5-nitro-2-methoxy-trans-cinnamic acid (69447-75-2,288151-91-7)

Guidance literature:

at 100 ℃;

DOI:10.1007/s12140-000-0005-6

Reference yield:

3-(2-hydroxy-5-nitrophenyl)acrylic acid (50396-49-1) + dimethyl sulfate (77-78-1) → 2-methoxy-5-nitro-cinnamic acid (69447-75-2,288151-91-7)

Guidance literature:

O-methyl-5-nitro-coumaric acid;

upstream raw materials:

3-(2-hydroxy-5-nitrophenyl)acrylic acid

dimethyl sulfate

2-methoxy-5-nitrobenzaldehyde

acetic anhydride

Downstream raw materials:

6-nitrocoumarin

5-nitro-2-methoxy-trans-cinnamic acid

mehyl (E)-3-(2-methoxy-5-nitrophenyl)propenoate

(E)-3-(5-nitro-2-methoxyphenyl)-N-methylacrylamide

Refernces