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Nitroethane

Nitroethane
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Names
IUPAC name
Nitroethane
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.081
KEGG
PubChem CID
RTECS number KI5600000
UN number UN 2842
Properties
C2H5NO2
Molar mass 75.07 g·mol−1
Density 1.054 g/cm3
Melting point −90 °C (−130 °F; 183 K)
Boiling point 112.0 to 116.0 °C (233.6 to 240.8 °F; 385.1 to 389.1 K)
Slightly soluble (4.6 g/100 ml at 20 °C)
Vapor pressure 21 mmHg (25 °C)
Acidity (pKa) 16.7
-35.4·10−6 cm3/mol
Viscosity 0.677 Pa·s at 20 °C
Hazards
Main hazards Flammable, harmful
Safety data sheet MSDS at fishersci.com
R-phrases R5 R10 R22
S-phrases S41
Flash point 28 °C (82 °F; 301 K)
Explosive limits 3.4%-?
Lethal dose or concentration (LD, LC):
5000 ppm (rabbit, 2 hr)
6250 ppm (mouse, 2 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 100 ppm (310 mg/m3)
REL (Recommended)
TWA 100 ppm (310 mg/m3)
IDLH (Immediate danger)
1000 ppm
Related compounds
2-Nitropropane
Nitromethane
Related compounds
Ethyl nitrite
Ethyl nitrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor.

Nitroethane is produced industrially by treating propane with nitric acid at 350–450 °C. This exothermic reaction produces four industrially significant nitroalkanes: nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane. The reaction involves free radicals, such as CH3CH2CH2O., which arise via homolysis of the corresponding nitrite ester. These alkoxy radicals are susceptible to C—C fragmentation reactions, which explains the formation of a mixture of products.

Alternatively, nitroethane can be produced by the Victor Meyer reaction with either bromoethane or iodoethane with silver nitrite in a diethyl ether solvent or with the Kornblum Modification which uses the prior mentioned alkyl halides with the less soluble sodium nitrite salt in either a dimethyl sulfoxide or dimethylformamide solvent.

Via condensations like the Henry reaction, nitroethane converts to several compounds of commercial interest. Condensation with 3,4-dimethoxybenzaldehyde affords the precursor to the antihypertensive drug methyldopa; condensation with unsubstituted benzaldehyde yields phenyl-2-nitropropene. Nitroethane condenses with two equivalents of formaldehyde to give, after hydrogenation, 2-amino-2-methyl-1,3-propanediol, which in turn condenses with oleic acid to give an oxazoline, which protonates to give a cationic surfactant.


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