Nitroethane

Nitroethane
IUPAC name nitroethane
Identifiers
CAS number	79-24-3 Y
PubChem	6587
ChemSpider	6338 Y
UN number	UN 2842
KEGG	C01837 Y
ChEBI	CHEBI:16268 N
ChEMBL	CHEMBL15625 Y
RTECS number	KI5600000
Jmol-3D images	Image 1
SMILES CC[N+](=O)[O-]
InChI InChI=1S/C2H5NO2/c1-2-3(4)5/h2H2,1H3 Y Key: MCSAJNNLRCFZED-UHFFFAOYSA-N Y InChI=1/C2H5NO2/c1-2-3(4)5/h2H2,1H3 Key: MCSAJNNLRCFZED-UHFFFAOYAB
Properties
Molecular formula	C2H5NO2
Molar mass	75.07 g/mol
Density	1.054 g/cm3, liquid
Melting point	-90 °C, 183 K, -130 °F
Boiling point	112.0–116.0 °C (385.2–389.2 K)
Solubility in water	slightly soluble (4.6 g/100 ml at 20°C)
Viscosity	0.677 Pa·s at 20 °C
Hazards
MSDS	MSDS at fishersci.com
R-phrases	R5 R10 R22
S-phrases	S41
Main hazards	Flammable, harmful
Flash point	28 °C
Related compounds
Related nitro compounds	nitromethane 1,1-dichloro-1-nitroethane
Related compounds	ethyl nitrite ethyl nitrate
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 colourless and has a fruity odor.

Preparation

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.^[1]

Uses

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.^[1]

Like some other nitrated organic compounds, nitroethane is also used as a fuel additive and a precursor to explosives.

Nitroethane is a useful solvent for polymers such as polystyrene and is particularly useful for dissolving cyanoacrylate adhesives.^{[citation needed]} In niche applications, it has been used as a component in artificial nail remover and in overhead ceiling sealant sprays.

Toxicity

Nitroethane is suspected to cause genetic damage and be harmful to the nervous system. Typical TLV/TWA is 100 ppm. Typical STEL is 150 ppm. Skin contact causes dermatitis in humans. In animal studies, nitroethane exposure was observed to cause lacrimation, dyspnea, pulmonary rales, edema, liver and kidney injury, and narcosis.^[2] Children have been poisoned by accidental ingestion of artificial nail remover.^[3]

The LD₅₀ for rats is reported as 1100 mg/kg.^[4]

References

1. ^ ^{a b} Sheldon B. Markofsky “Nitro Compounds, Aliphatic” Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a17_401.
2. ^ [http://www.osha.gov/dts/chemicalsampling/data/CH_257200.html "Chemical Sampling Information Nitroethane." Retrieved February 9, 2007, from the website of the US Occupational Safety & Health Administration.]
3. ^ Hornfeldt CS, Rabe WH (1994). "Nitroethane poisoning from an artificial fingernail remover". J. Toxicol. Clin. Toxicol. 32 (3): 321–4. PMID 8007041. 
4. ^ MSDS for nitroethane (revised October 3, 2005), as reported by Fisher Scientific.

External links

• WebBook page for C2H5NO2