Nitroethylene

Base Information

• Chemical Name: Nitroethylene
• CAS No.: 3638-64-0
• Molecular Formula: C2H3NO2
• Molecular Weight: 73.0513
• Hs Code.: 2904209090
• European Community (EC) Number: 687-643-6
• DSSTox Substance ID: DTXSID0075235
• Nikkaji Number: J149.597F
• Wikipedia: Nitroethylene
• Wikidata: Q5273015
• Metabolomics Workbench ID: 57637
• Mol file: 3638-64-0.mol

Synonyms:Nitroethylene;Nitroethene;3638-64-0;Ethene, nitro-;1-nitroethene;1-nitroethylene;CH2=CHNO2;C2H3NO2;26618-70-2;1-Nitroethene (~ 1 mole/L in Toluene);aci-nitroethylene;Ethylene, nitro-;DTXSID0075235;nitroethene (2.5M in toluene);CHEBI:51131;AMY36706;AKOS005146539;AT20025;LS-67657;NITROETHENE SOLUTION (1M IN XYLENE);A6293;FT-0652362;EN300-86457;Q5273015

Chemical Property of Nitroethylene

Chemical Property:

• Vapor Pressure: 45.8mmHg at 25°C
• Melting Point: -55.5°C
• Refractive Index: 1.406
• Boiling Point: 98.5 °C at 760 mmHg
• Flash Point: 23.2 °C
• PSA: 45.82000
• Density: 1.052 g/cm³
• LogP: 0.92980
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 73.016378338
• Heavy Atom Count: 5
• Complexity: 53.2

Purity/Quality:

97% ^*data from raw suppliers

1-Nitroethene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C[N+](=O)[O-]
• General Description: Nitroethylene is a stable and versatile reagent in organic synthesis, capable of participating in (4 + 2) cycloadditions, Michael additions, and ene reactions to yield functionalized products such as nitronorbornenes and nitroethyl-substituted compounds. Its stability as a benzene solution under refrigeration and its reactivity with diverse substrates, including cyclopentadienes, enamines, and terpenes, make it a valuable synthon for constructing complex molecular frameworks with potential for further derivatization.

Technology Process of Nitroethylene

There total 36 articles about 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: 89.0%

2-nitro-1-ethanol (625-48-9) → 1-nitroethylene (3638-64-0,26618-70-2)

Guidance literature:

With phthalic anhydride; at 150 - 180 ℃; under 80 Torr;

DOI:10.1021/jo026187p

Reference yield: 80.0%

acrylic acid (79-10-7) → 1-nitroethylene (3638-64-0,26618-70-2)

Guidance literature:

With tert.-butylnitrite; silica gel; In acetonitrile; at 100 ℃; under 2250.23 Torr; Time; Temperature; Pressure; Microwave irradiation;

DOI:10.1080/00397911.2012.735331

Reference yield: 80.0%

phthalic anhydride (85-44-9) + 2-nitro-1-ethanol (625-48-9) → 1-nitroethylene (3638-64-0,26618-70-2)

Guidance literature:

at 140 - 180 ℃; under 80 Torr; Heating;

DOI:10.1021/jo01295a003

upstream raw materials:

phthalic anhydride

2-nitro-1-ethanol

formaldehyd

nitromethane

Downstream raw materials:

3-(2-nitroethyl)indole

decan-5-one oxime

1-nitrohexane

N,N-bis-(2-nitro-ethyl)-aniline

Refernces

Nitroethylene: A Stable, Clean, and Reactive Agent for Organic Synthesis

10.1021/jo01295a003

The study investigates the stability and reactivity of nitroethylene as a useful synthon in organic synthesis. The researchers found that nitroethylene is stable as a standard solution in benzene when stored in a refrigerator for at least six months. They prepared nitroethylene through the phthalic anhydride-mediated dehydration of 2-nitroethanol. The study explores nitroethylene's involvement in various reactions, including (4 + 2) cycloadditions with cyclopentadienes and their derivatives, Michael additions with enamines like indole and 1-morpholinocyclohexene, and ene reactions with substrates such as α-pinene. The products formed, such as 2-endo-nitronorbornene, 7-syn-(methoxymethyl)-2-endo-nitrobicyclo[2.2.1]heptene, and 3-(nitroethyl)indole, demonstrate nitroethylene's potential as a versatile reagent for synthesizing functionalized systems with further elaboration possibilities. The study highlights nitroethylene's stability and its ability to participate in diverse organic reactions, suggesting its potential for broader application in synthetic chemistry.

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