1-(4-Methoxyphenyl)-2-nitroethylene

Base Information

• Chemical Name: 1-(4-Methoxyphenyl)-2-nitroethylene
• CAS No.: 3179-10-0
• Molecular Formula: C9H9NO3
• Molecular Weight: 179.175
• Mol file: 3179-10-0.mol

Synonyms:Anisole,p-(2-nitrovinyl)- (6CI,7CI,8CI);1-(4-Methoxyphenyl)-2-nitroethene;1-Methoxy-4-(2-nitroethenyl)benzene;1-Methoxy-4-(2-nitrovinyl)benzene;2-(4-Methoxyphenyl)-1-nitroethene;2-(4-Methoxyphenyl)nitroethylene;4-(2-Nitrovinyl)anisole;4-Methoxy-b-nitrostyrene;4-Methoxy-w-nitrostyrene;Chembridge 5102117;NSC 23856;p-(2-Nitrovinyl)anisole;p-Methoxy-b-nitrostyrene;

Chemical Property of 1-(4-Methoxyphenyl)-2-nitroethylene

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 0.000735mmHg at 25°C
• Melting Point: 86-88 °C(lit.)
• Refractive Index: 1.58
• Boiling Point: 317 °C at 760 mmHg
• Flash Point: 153.5 °C
• PSA: 55.05000
• Density: 1.189 g/cm³
• LogP: 2.46580
• Storage Temp.: Keep Cold
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 179.058243149
• Heavy Atom Count: 13
• Complexity: 190

Purity/Quality:

97% ^*data from raw suppliers

1-Methoxy-4-(2-nitrovinyl)benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=C[N+](=O)[O-]
• General Description: Based on the provided literature, **1-(4-Methoxyphenyl)-2-nitroethylene** (also known as *trans-4-methoxy-β-nitrostyrene* or *T4MN*) exhibits **vasorelaxant properties** in vascular tissues. Studies indicate it induces relaxation in rat mesenteric resistance arteries and thoracic aorta, potentially through mechanisms involving **soluble guanylate cyclase (sGC)-dependent pathways** or other vascular smooth muscle modulation. Its effects are distinct from structurally related nitro compounds, suggesting specific pharmacological activity. No relevant data were found regarding its role in nitroaldol condensation or synthetic applications in the provided abstracts. **Returned paragraph (conclusion):** *1-(4-Methoxyphenyl)-2-nitroethylene (T4MN) demonstrates vasorelaxant effects in rat vascular tissues, likely mediated via sGC-dependent pathways or direct smooth muscle modulation, distinguishing it from analogous nitro compounds. No relevant synthetic or catalytic roles were identified in the provided literature.*

Technology Process of 1-(4-Methoxyphenyl)-2-nitroethylene

There total 66 articles about 1-(4-Methoxyphenyl)-2-nitroethylene 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%

nitromethane (75-52-5) + 4-methoxy-benzaldehyde (123-11-5) → (E)-1-methoxy-4-(2-nitrovinyl)benzene (3179-10-0,5576-97-6)

Guidance literature:

With hexan-1-amine; In toluene; at 90 ℃; for 3h;

DOI:10.1016/j.tetlet.2017.12.050

Reference yield: 99.0%

nitromethane (75-52-5) + 4-methoxy-benzaldehyde (123-11-5) → 1-methoxy-4-(2-nitro-vinyl)-benzene (3179-10-0)

Guidance literature:

With ethylenediamine functionalized magnetic Fe₃O₄ supported on SiO₂ nanoparticles; air; at 80 ℃; for 4h; Reagent/catalyst; Temperature; Time;

DOI:10.1039/c5ra11798d

Reference yield: 95.0%

(E)-4-(2-bromo-vinyl)-anisole (6303-59-9,60592-52-1,27570-08-7) → (E)-1-methoxy-4-(2-nitrovinyl)benzene (3179-10-0,5576-97-6)

Guidance literature:

With tetranitromethane; In acetonitrile; Irradiation;

upstream raw materials:

diethyl ether

1-(4-Methoxyphenyl)-2-nitro-1-buten-3-one

nitromethane

4-methoxy-benzaldehyde

Downstream raw materials:

4-(1,2-dibromo-2-nitro-ethyl)-anisole

2-(p-methoxyphenyl)-2-methoxyethylamine

β-ethoxy-4-methoxy-phenethylamine

4-Methoxyphenethylamine