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| Names | |||
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| Preferred IUPAC name Nitroethane | |||
| Identifiers | |||
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3D model (JSmol) | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.001.081 | ||
| KEGG |
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| RTECS number |
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| UNII | |||
| UN number | UN 2842 | ||
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| Properties | |||
| C2H5NO2 | |||
| Molar mass | 75.067 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Density | 1.054 g/cm3 | ||
| Melting point | −89.42 °C (−128.96 °F; 183.73 K)[4] | ||
| Boiling point | 114 °C (237 °F; 387 K) | ||
| Slightly soluble (4.6 g/100 ml at 20 °C) | |||
| Vapor pressure | 21 mmHg (25 °C)[1] | ||
| Acidity (pKa) | 16.7[2][3] | ||
| −35.4·10−6 cm3/mol | |||
| Viscosity | 0.677mPa·s at 20 °C | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | Flammable, harmful | ||
| GHS labelling: | |||
   | |||
| Danger | |||
| H226,H302,H315,H331,H341,H412 | |||
| P210,P261,P301,P304,P312,P330,P340,P370,P378,P403+P233 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 28 °C (82 °F; 301 K) | ||
| 414 °C (777 °F; 687 K) | |||
| Explosive limits | 3.4%-?[1] | ||
| Lethal dose or concentration (LD, LC): | |||
LC50 (median concentration) | 5000 ppm (rabbit, 2 hr)[5] | ||
LCLo (lowest published) | 6250 ppm (mouse, 2 hr)[5] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 100 ppm (310 mg/m3)[1] | ||
REL (Recommended) | TWA 100 ppm (310 mg/m3)[1] | ||
IDLH (Immediate danger) | 1000 ppm[1] | ||
| Safety data sheet (SDS) | MSDS at fishersci.com | ||
| Related compounds | |||
Relatednitro compounds | 2-Nitropropane Nitromethane | ||
Related compounds | Ethyl nitrite Ethyl nitrate | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Nitroethane is anorganic compound having the chemical formula C2H5NO2. Similar in many regards tonitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor.
Nitroethane is produced industrially by treatingpropane withnitric acid at 350–450 °C. Thisexothermic reaction produces four industrially significant nitroalkanes:nitromethane, nitroethane,1-nitropropane, and2-nitropropane. The reaction involves free radicals, such as CH3CH2CH2O., which arise via homolysis of the corresponding nitriteester. These alkoxy radicals are susceptible to C—C fragmentation reactions, which explains the formation of a mixture of products.[6]
Alternatively, nitroethane can be produced by theVictor Meyer reaction of haloethanes such aschloroethane,bromoethane, oriodoethane with silver nitrite indiethyl ether orTHF. The Kornblum modification of this reaction usessodium nitrite in either adimethyl sulfoxide ordimethylformamide solvent.[7]
Via condensations like theHenry reaction, nitroethane converts to several compounds of commercial interest. Condensation with3,4-dimethoxybenzaldehyde affords the precursor to theantihypertensive drugmethyldopa; condensation with unsubstituted benzaldehyde yieldsphenyl-2-nitropropene, a precursor for amphetamine drugs. Nitroethane condenses with two equivalents offormaldehyde to give, afterhydrogenation, 2-amino-2-methyl-1,3-propanediol, which in turn condenses with oleic acid to give an oxazoline, which protonates to give a cationicsurfactant.[6]
Like some other nitrated organic compounds, nitroethane is also used as afuel additive anda precursor torocket propellants.[citation needed]
Nitroethane is a useful solvent for polymers such aspolystyrene and is particularly useful for dissolvingcyanoacrylate adhesives. In cosmetics applications, it has been used as a component inartificial nail remover and in overhead ceiling sealant sprays.
Nitroethane was previously used successfully as a chemical feedstock (precursor ingredient) in laboratories for the synthesis of multitudes of substances and consumer goods. For example, the medicinePervitin (methamphetamine) was commonly used in the 19th and 20th century, and was especially popular during WWII by troops of both sides for mood elevation, appetite and sleep suppression and increasing focus and alertness). Nitroalkanes were one of many ingredients used in the synthesis of manyphenethylamines, including medications such as Pervitin and theracemic compoundBenzedrine[8] (amphetamine), used as ananorectic medicine for obesity.[9]
Nitroethane is suspected to cause genetic damage and be harmful to thenervous system. Typical TLV/TWA is 100 ppm. Typical STEL is 150 ppm. Skin contact causesdermatitis in humans. In animal studies, nitroethane exposure was observed to causelacrimation,dyspnea, pulmonary rales,edema, liver and kidney injury, and narcosis.[10] Children have been poisoned by accidental ingestion of artificial nail remover.[11]
TheLD50 for rats is reported as 1100 mg/kg.[12]
