1238305-24-2

Basic information

• Product Name: (Z)-N-(2-nitrovinyl)acetaMide
• Synonyms: (Z)-N-(2-nitrovinyl)acetaMide
• CAS NO: 1238305-24-2
• Molecular Formula: C₄H₆N₂O₃
• Molecular Weight: 130.10204
• Mol File: 1238305-24-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z)-N-(2-nitrovinyl)acetaMide(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-N-(2-nitrovinyl)acetaMide(1238305-24-2)
• EPA Substance Registry System: (Z)-N-(2-nitrovinyl)acetaMide(1238305-24-2)

Safety Data

• Hazardous Substances Data: 1238305-24-2(Hazardous Substances Data)

Usage

Description

(Z)-N-(2-nitrovinyl)acetaMide, with the molecular formula C6H8N2O4, is a nitro compound characterized by a vinyl group attached to a nitro group and an acetamide functional group. It is a yellow to brown solid with a melting point of approximately 76-78°C and is sparingly soluble in water. This chemical compound is predominantly utilized as a raw material in the synthesis of pharmaceuticals and pesticides, making it a significant intermediate in organic synthesis.

Uses

Used in Pharmaceutical Industry:
(Z)-N-(2-nitrovinyl)acetaMide is used as a raw material for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medical treatments.
Used in Pesticide Industry:
In the pesticide industry, (Z)-N-(2-nitrovinyl)acetaMide is used as a raw material for the production of agrochemicals. Its incorporation into these products aids in the development of effective pest control solutions, which are crucial for maintaining agricultural productivity and food security.
Used in Organic Synthesis:
(Z)-N-(2-nitrovinyl)acetaMide also serves as an intermediate in organic synthesis, where it can be used to create a variety of complex organic compounds. Its versatility in this field makes it a valuable asset for researchers and chemists working on the development of new materials and substances.
Precaution:
Due to its potential hazards and health risks, (Z)-N-(2-nitrovinyl)acetaMide should be handled and stored with care to ensure the safety of those working with it and to minimize any negative environmental impacts.

Upstream product

• 108-24-7 acetic anhydride 
• 29270-77-7 1-amino-2-nitroethylene 
• 86602-46-2 (Z)-2-nitroethylene-1-amine 

Downstream Products

• 1238305-30-0 N-(2-benzyl-1-nitromethyl-3-oxopropyl)acetamide 
• 1226768-14-4 N-((2R,3S)-1-nitro-4-oxo-3-(pentan-3-yloxy)butan-2-yl)acetamide 
• 1402431-73-5 N-(1-nitro-4-oxo-3-phenoxybutan-2-yl)acetamide 
• 1402431-74-6 N-(1-nitro-4-oxo-3-phenoxybutan-2-yl)acetamide 
• 1402431-71-3 N-(1-nitro-4-oxo-3-phenoxybutan-2-yl)acetamide 
• 1402431-72-4 N-(1-nitro-4-oxo-3-phenoxybutan-2-yl)acetamide 
• 1402431-90-6 N-{3-[(4-methoxybenzyl)oxy]-1-nitro-4-oxobutan-2-yl}acetamide 
• 1402431-89-3 N-{3-[(4-methoxybenzyl)oxy]-1-nitro-4-oxobutan-2-yl}acetamide 
• 1402431-87-1 N-{3-[(4-methoxybenzyl)oxy]-1-nitro-4-oxobutan-2-yl}acetamide 
• 1402431-88-2 N-{3-[(4-methoxybenzyl)oxy]-1-nitro-4-oxobutan-2-yl}acetamide 
• 1402431-77-9 N-[3-(benzyloxy)-1-nitro-4-oxobutan-2-yl]acetamide 
• 1402431-75-7 N-[3-(benzyloxy)-1-nitro-4-oxobutan-2-yl]acetamide 
• 1402431-78-0 N-[3-(benzyloxy)-1-nitro-4-oxobutan-2-yl]acetamide 
• 1402431-76-8 N-[(2R,3S)-1-nitro-4-oxo-3-benzyloxybutan-2-yl]acetamide 

Relevant articles and documents

Stereoisomers of oseltamivir-synthesis, in silico prediction and biological evaluation

Oseltamivir is an important antiviral drug, which possess three chirality centers in its structure. From eight possible stereoisomers, only two have been synthesized and evaluated so far. We describe herein the stereoselective synthesis, computational activity prediction and biological testing of another three diastereoisomers of oseltamivir. These isomers have been synthesized using stereoselective organocatalytic Michael addition, cyclization and reduction. Their binding to viral neuraminidase N1 of influenza A virus was evaluated by quantum-chemical calculations and their anti-influenza activities were tested by an in vitro virus-inhibition assay. All three isomers displayed antiviral activity lower than that of oseltamivir, however, one of the stereoisomers, (3S,4R,5S)-isomer, of oseltamivir showed in vitro potency towards the Tamiflu-sensitive influenza viral strain A/Perth/265/2009(H5N1) comparable to Tamiflu.

Thiol-free synthesis of oseltamivir and its analogues via organocatalytic michael additions of oxyacetaldehydes to 2-acylaminonitroalkenes

The organocatalytic addition of substituted oxyacetaldehydes to 2-acylaminonitroethenes proceeded with good to high diastereoselectivities and enantioselectivities. The resulting adducts reacted with ethyl 2-(diethoxyphosphoryl) acrylate to afford highly functionalized cyclohexenes. A thiol-free protocol for cyclization has been developed that leads to a separable mixture of two diastereoisomers. The unwanted diastereoisomer can be efficiently epimerized. The resulting cyclohexenes are precursors to oseltamivir and its analogues. The synthesis of the key reagent, 3-pentyloxyaldehyde, was also improved. Georg Thieme Verlag Stuttgart · New York.

Organocatalytic michael addition of aldehydes to protected 2-amino-1-nitroethenes: The practical syntheses of oseltamivir (tamiflu) and substituted 3-aminopyrrolidines

Figure Presented Hey Mickey, you're so fine! Organocatalytic Michael additions of aldehydes with protected 2-amino-1-nitroethene could go through three different transition-states to afford adducts with usual and unusual stereochemistry, thereby providing a facile entry to Tamiflu (see scheme) and substituted 3-aminopyrrolidines. TMS = trimethylsilyl, Ac = acetyl.