4-Methoxy-beta-nitrostyrene

Base Information

• Chemical Name: 4-Methoxy-beta-nitrostyrene
• CAS No.: 5576-97-6
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.175
• Hs Code.: 2909309090
• European Community (EC) Number: 627-574-0,667-607-6
• NSC Number: 23856
• DSSTox Substance ID: DTXSID00879773
• Nikkaji Number: J450.248E,J316.180C
• Wikidata: Q72517808
• Metabolomics Workbench ID: 45636
• ChEMBL ID: CHEMBL231046
• Mol file: 5576-97-6.mol

Synonyms:4-methoxy-beta-nitrostyrene;4-methyl-beta-nitrostyrene;T4MeN compound;T4MN compound;trans-4-methoxy-beta-nitrostyrene;trans-4-methyl-beta-nitrostyrene

Chemical Property of 4-Methoxy-beta-nitrostyrene

Chemical Property:

• Melting Point: 86-88 °C (lit.)
• 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.: Sealed in dry,Room Temperature
• Solubility.: chloroform: soluble25mg/mL, clear, yellow
• 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

4-Methoxy-β-nitrostyrene ^*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-]
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C/[N+](=O)[O-]
• Uses: trans-4-Methoxy-β-nitrostyrene acts as guest molecule and forms guest molecules forming co-crystal phases with the d-form of robust syndiotactic polystyrene (sPS). It may be employed as a Michael acceptor in the synthesis of proline based chiral ionic liquid catalysts with two five-membered unsaturated aza-heterocycles.

Technology Process of 4-Methoxy-beta-nitrostyrene

There total 33 articles about 4-Methoxy-beta-nitrostyrene 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: 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;

Reference yield: 95.0%

(E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) → (E)-1-methoxy-4-(2-nitrovinyl)benzene (3179-10-0,5576-97-6)

Guidance literature:

With tert.-butylnitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In acetonitrile; at 50 ℃; for 3h; Solvent; Temperature; Reagent/catalyst; Time; stereoselective reaction;

DOI:10.1039/c3cc41576g

upstream raw materials:

1-(4-methoxy-phenyl)-2-nitro-ethanol

nitromethane

4-methoxy-benzaldehyde

n-Pentylamine

Downstream raw materials:

(1-(4-methoxyphenyl)-2-nitroethyl) phenyl sulfide

2-<(furylmethyl)oxy>-2-(4-methoxyphenyl)-1-nitroethane

6-Hydrazino-5-[1-(4-methoxy-phenyl)-2-nitro-ethyl]-1,3-dimethyl-1H-pyrimidine-2,4-dione

6-Hydroxyamino-5-[1-(4-methoxy-phenyl)-2-nitro-ethyl]-1,3-dimethyl-1H-pyrimidine-2,4-dione

Refernces

Scope and limitations of cyclopropanations with sulfur ylides

10.1021/ja1084749

The study conducted by Roland Appel, Nicolai Hartmann, and Herbert Mayr from the Department of Chemistry at Ludwig-Maximilians-Universit?t München, investigates the cyclopropanation reactions using sulfur ylides. It focuses on the rates of reactions between stabilized and semistabilized sulfur ylides with benzhydrylium ions and Michael acceptors, measured using UV-vis spectroscopy in DMSO at 20°C. The research establishes a correlation between the second-order rate constants (log k2) and the electrophilicity parameters (E) of the electrophiles, which aids in calculating the nucleophile-specific parameters (N and s) for the sulfur ylides. The findings indicate that the rate constants for cyclopropanation reactions with Michael acceptors align with those for carbocations, suggesting a stepwise mechanism with the initial nucleophilic attack being rate-determining. This study provides a quantitative approach to understanding sulfur ylide reactivity, which is crucial for predicting the scope and limitations of cyclopropanation reactions in organic synthesis.

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