4-methoxy-6-(2-nitroethyl)-2H-1,3-benzodioxole

Base Information

• Chemical Name: 4-methoxy-6-(2-nitroethyl)-2H-1,3-benzodioxole
• CAS No.: 15896-78-3
• Molecular Formula: C10H9 N O5
• Molecular Weight: 223.185
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID40696547
• Wikidata: Q82626187
• Mol file: 15896-78-3.mol

Synonyms:15896-78-3;4-methoxy-6-(2-nitroethyl)-1,3-benzodioxole;4-methoxy-6-(2-nitroethyl)-2H-1,3-benzodioxole;DTXSID40696547;4-Methoxy-6-(2-nitroethanyl)-1,3-benzodioxole;4-Methoxy-6-(2-nitroethyl)benzo[d][1,3]dioxole

Chemical Property of 4-methoxy-6-(2-nitroethyl)-2H-1,3-benzodioxole

Chemical Property:

• Vapor Pressure: 2.91E-05mmHg at 25°C
• Refractive Index: 1.613
• Boiling Point: 367.3°Cat760mmHg
• Flash Point: 177.2°C
• PSA: 73.51000
• Density: 1.378g/cm³
• LogP: 1.76630
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 225.06372245
• Heavy Atom Count: 16
• Complexity: 254

Purity/Quality:

4-METHOXY-6-(2-NITROETHANYL)-1,3-BENZODIOXOLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC2=C1OCO2)CC[N+](=O)[O-]

Technology Process of 4-methoxy-6-(2-nitroethyl)-2H-1,3-benzodioxole

There total 7 articles about 4-methoxy-6-(2-nitroethyl)-2H-1,3-benzodioxole 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: 87.0%

nitromethane (75-52-5) + 3-methoxy-4,5-methylenedioxybenzaldehyde (5780-07-4) → (E)-4-methoxy-6-(2-nitrovinyl)benzo[d][1,3]dioxole (15896-78-3)

Guidance literature:

With ammonium acetate; acetic acid;

DOI:10.1021/ja026788y

Reference yield:

3-methoxy-4,5-methylenedioxybenzaldehyde (5780-07-4) → (E)-4-methoxy-6-(2-nitrovinyl)benzo[d][1,3]dioxole (15896-78-3)

Guidance literature:

With ammonium acetate; In nitromethane; water; acetic acid;

Reference yield:

vanillin (121-33-5,8014-42-4) → (E)-4-methoxy-6-(2-nitrovinyl)benzo[d][1,3]dioxole (15896-78-3)

Guidance literature:

Multi-step reaction with 4 steps

1: iodine; potassium iodide; potassium carbonate / water / 4.5 h / 20 °C

2: potassium hydroxide; copper(l) iodide / water; dimethyl sulfoxide / 11 h / 110 °C / Autoclave

3: copper(II) oxide; potassium carbonate / N,N-dimethyl-formamide / 3 h / 110 °C

4: acetic acid; ammonium acetate / 2 h / 101 °C

With copper(l) iodide; ammonium acetate; iodine; potassium carbonate; acetic acid; potassium iodide; copper(II) oxide; potassium hydroxide; In water; dimethyl sulfoxide; N,N-dimethyl-formamide; 4: |Henry Nitro Aldol Condensation;

DOI:10.1021/acs.orglett.9b02715

upstream raw materials:

nitromethane

3-methoxy-4,5-methylenedioxybenzaldehyde

vanillin

5-iodovaniline

Downstream raw materials:

β-(3-methoxy-4,5-methylenedioxy)phenylethylamine

(±)-β-N-demethyl noscapine

(±)-β-noscapine

N-[2-(7-methoxy-benzo[1,3]dioxol-5-yl)-ethyl]-N-(3-methoxy-benzyl)-formamide

Refernces

• 1、 Pettit, Robin K.,Pettit, George R.,Hamel, Ernest,Hogan, Fiona,Moser, Bryan R.,Wolf, Sonja,Pon, Sandy,Chapuis, Jean-Charles,Schmidt, Jean M.. "E-Combretastatin and E-resveratrol structural modifications: Antimicrobial and cancer cell growth inhibitory β-E-nitrostyrenes". experimental part. p. 6606 - 6612. Retrieved 2009/12/06.
• 2、 -. "Endothelin antagonists". . . Retrieved 2008/06/13.