Nitroethane: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 415867396

| Name = Nitroethane

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageFile =

| ImageFileL1 = Nitroethane-2D-skeletal.png

| ImageFileR1_Ref = {{chemboximage|correct|??}}

| ImageFileR1 = Nitroethane-2D-flat.png

| ImageFile2 = Nitroethane-3D-balls.png

| ImageSize2 = 150px

| ImageName1 = Nitroethane

| PIN = Nitroethane

| OtherNames =

| SystematicName =

| Section1 = {{Chembox Identifiers

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 16268

| SMILES = CC[N+](=O)[O-]

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 6338

| PubChem = 6587

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C01837

| InChI = 1/C2H5NO2/c1-2-3(4)5/h2H2,1H3

| InChIKey = MCSAJNNLRCFZED-UHFFFAOYAB

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 15625

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C2H5NO2/c1-2-3(4)5/h2H2,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = MCSAJNNLRCFZED-UHFFFAOYSA-N

| CASNo = 79-24-3

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6KEL3ZAU0V

| RTECS = KI5600000

| UNNumber = UN 2842

| Section2 = {{Chembox Properties

| C = 2 | H = 5 | N = 1 | O = 2

| Appearance = Colorless liquid

| Density = 1.054 g/cm³

| Solubility = Slightly soluble (4.6 g/100 ml at 20 °C)

<!-- | Freezing Point = -89.42°C (-130°F or 183.7 K) this parameter does not exist-->

| MeltingPtC = -51

| BoilingPtC = 114

| BoilingPt_notes =

<!-- | Flash Point = 41°C ( 106°F or 314.15 K) this parameter does not exist-->

<!-- | Autoignition = 415°C( 779°F or 688.15K) this parameter does not exist-->

| Viscosity = 0.677 [[milliPascal second|mPa·s]] at 20 °C

| VaporPressure = 21 mmHg (25 °C)<ref name=PGCH/>

| pKa = 16.7<ref name=uwisconsin>{{cite web|last1=Reich|first1=Hans|title=Bordwell pKa table: "Nitroalkanes"|url=http://www.chem.wisc.edu/areas/reich/pkatable/|website=University of Wisconsin Chemistry Department|accessdate=17 January 2016}}</ref><ref name=walterjacs>{{cite journal|last1=Matthews|first1=Walter|title=Equilibrium acidities of carbon acids. VI. Establishment of an absolute scale of acidities in dimethyl sulfoxide solution|journal=Journal of the American Chemical Society|date=1975|volume=97|issue=24|page=7006|doi=10.1021/ja00857a010|display-authors=etal}}</ref>

| MagSus = -35.4·10⁻⁶ cm³/mol

| Section3 =

| Section4 =

| Section5 =

| Section6 =

| Section7 = {{Chembox Hazards

| ExternalSDS = [https://fscimage.fishersci.com/msds/65832.htm MSDS at fishersci.com]

| MainHazards = Flammable, harmful

| FlashPtC = 28

| GHSPictograms = {{GHS02}} {{GHS06}} {{GHS08}}

| GHSSignalWord = '''DANGER'''

| HPhrases = {{H-phrases|226|302|315|331|341|412}}

| PPhrases = {{P-phrases|210|261|301|330|304|340|312|370|378|403+233}}

| NFPA-F = 3

| NFPA-H = 2

| NFPA-R = 3

| IDLH = 1000 ppm<ref name=PGCH>{{PGCH|0453}}</ref>

| LC50 = 5000 ppm (rabbit, 2 hr)<ref name=IDLH>{{IDLH|79243|Nitroethane}}</ref>

| REL = TWA 100 ppm (310 mg/m³)<ref name=PGCH/>

| PEL = TWA 100 ppm (310 mg/m³)<ref name=PGCH/>

| ExploLimits = 3.4%-?<ref name=PGCH/>

| LCLo = 6250 ppm (mouse, 2 hr)<ref name=IDLH/>

| Section8 = {{Chembox Related

| OtherFunction_label = [[nitro compounds]]

| OtherFunction = [[2-Nitropropane]]<br />[[Nitromethane]]

| OtherCompounds = [[Ethyl nitrite]]<br />[[Ethyl nitrate]]

'''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&nbsp;°C. This [[exothermic]] reaction produces four industrially significant nitroalkanes: [[nitromethane]], nitroethane, [[1-nitropropane]], and [[2-Nitropropane|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.<ref name=Markofsky>Sheldon B. Markofsky “Nitro Compounds, Aliphatic” in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2002. {{doi|10.1002/14356007.a17_401}}.</ref>

Alternatively, nitroethane can be produced by the [[Victor Meyer]] reaction of haloethanes such as [[chloroethane]], [[bromoethane]], or [[iodoethane]] with silver nitrite in [[diethyl ether]] or [[THF]]. The Kornblum modification of this reaction uses [[sodium nitrite]] in either a [[dimethyl sulfoxide]] or [[dimethylformamide]] solvent.<ref name="Victor Meyer Reaction">{{cite book|last=Agrawal|first=Jai|title=Organic Chemistry of Explosives|year=2007|publisher=John Wiley & Sons|location=Chichester, England|isbn=9780470029671|pages=7–10|url=https://www.scribd.com/doc/77304293/12/Modi%EF%AC%81ed-Victor-Meyer-Reaction}}</ref>

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]], a precursor for amphetamine drugs. 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]].<ref name=Markofsky/>

Like some other nitrated organic compounds, nitroethane is also used as a [[fuel additive]] and a precursor to [[Rocket propellant]]s.

Nitroethane is a useful solvent for polymers such as [[polystyrene]] and is particularly useful for dissolving [[cyanoacrylate]] adhesives. In cosmetics applications, it has been used as a component in [[manicure|artificial 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 medicine [[Pervitin]] (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 many [[phenethylamine]]s, including medications such as Pervitin and the [[racemic]] compound [[Benzedrine]]<ref>{{Cite web | url = https://www.da.gov/resource-center/2016%20NDTA%20Summary.pdf | title = 2016 National Drug Assessment Summary | date = November 2016 | publisher = [[Drug Administration]]}}</ref> (amphetamine), used as an [[anorectic]] medicine for obesity.<ref>{{Cite web | url = https://www.da.gov/resource-center/2016%20NDTA%20Summary.pdf | title = 2016 National Drug Assessment Summary | date = November 2016 | publisher = [[Drug Administration]]}}</ref>

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.<ref>[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.]</ref> Children have been poisoned by accidental ingestion of artificial nail remover.<ref>{{cite journal |author=Hornfeldt CS, Rabe WH |title=Nitroethane poisoning from an artificial fingernail remover |journal=J. Toxicol. Clin. Toxicol. |volume=32 |issue=3 |pages=321–4 |year=1994 |pmid=8007041 |doi=10.3109/15563659409017967}}</ref>

* [https://www.cdc.gov/niosh/npg/npgd0453.html CDC - NIOSH Pocket Guide to Chemical Hazards]

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[[Category:Nitroalkanes]]