155988-20-8

Basic information

• Product Name: 1-nitro-2-(2-nitroethyl)benzene
• Synonyms: 1-nitro-2-(2-nitroethyl)benzene
• CAS NO: 155988-20-8
• Molecular Weight: 196.163
• Mol File: 155988-20-8.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 1-nitro-2-(2-nitroethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-nitro-2-(2-nitroethyl)benzene(155988-20-8)
• EPA Substance Registry System: 1-nitro-2-(2-nitroethyl)benzene(155988-20-8)

Safety Data

• Hazardous Substances Data: 155988-20-8(Hazardous Substances Data)

Upstream product

• 3156-39-6 (E)-1-nitro-2-(2-nitrovinyl)benzene 
• 5670-66-6 1-nitro-2-(2-nitrovinyl)benzene 
• 552-89-6 2-nitro-benzaldehyde 
• 18731-43-6 2-nitro-1-(2-nitro-phenyl)-ethanol 

Relevant articles and documents

Reduction of α,β-unsaturated nitroolefins into nitroalkanes with Hantzsch ester promoted by isothiouronium salts

α,β-Unsaturated nitroolefins were reduced into nitroalkanes with a Hantzsch ester, promoted by S-benzyl isothiouronium iodide. The reactions proceeded successfully to afford the desired products in high yields and with excellent chemoselectivity.

Useful extensions of the henry reaction: Expeditious routes to nitroalkanes and nitroalkenes in aqueous media

The products of the Henry nitroaldol reaction from nitromethane and several aldehydes were reduced to the corresponding nitroalkanes with (n-Bu) 3SnH in water under microwave irradiation (80 °C/10 min), or dehydrated to the corresponding nitroalkenes with K2CO3 in water (generally 0-5 °C/20 min). Both "one-pot" reactions occur in excellent yields across a range of aliphatic and aromatic (including heteroaromatic) substrates. It seems likely that the deoxygenation of the nitroaldols occurs via coordination of an oxygen atom of the nitro group with a tin atom, which facilitates hydride delivery in the transition state. The elimination of water from the nitroaldols in mild base is likely driven by the stability of the conjugated nitroalkene products. The elimination required workup with 2 N HCl, which likely displaces a nitroalkane-nitroalkene equilibrium towards the latter. These extensions of the Henry reaction lead to products not easily obtained otherwise.

An intramolecular nitro-Mannich route to functionalised tetrahydroquinolines

A simple protocol for the diastereoselective synthesis of 3-nitrotetrahydroquinolines has been developed using an intramolecular nitro-Mannich reaction. In situ formation of an imine generated from treatment of 2-(2-nitroethyl)phenylamine with an aldehyde