Nitroethane

Last updated
Nitroethane
Nitroethane-2D-skeletal.png
Nitroethane-2D-flat.png
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Names
Preferred IUPAC name
Nitroethane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.081 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
RTECS number
  • KI5600000
UNII
UN number UN 2842
  • InChI=1S/C2H5NO2/c1-2-3(4)5/h2H2,1H3 Yes check.svgY
    Key: MCSAJNNLRCFZED-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H5NO2/c1-2-3(4)5/h2H2,1H3
    Key: MCSAJNNLRCFZED-UHFFFAOYAB
  • CC[N+](=O)[O-]
Properties
C2H5NO2
Molar mass 75.067 g·mol−1
AppearanceColorless liquid
Density 1.054 g/cm3
Melting point −51 °C (−60 °F; 222 K)
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 0.677 mPa·s at 20 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable, harmful
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg
Danger
H226, H302, H315, H331, H341, H412
P210, P261, P301, P304, P312, P330, P340, P370, P378, P403+P233
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
2
3
3
Flash point 28 °C (82 °F; 301 K)
Explosive limits 3.4%-? [1]
Lethal dose or concentration (LD, LC):
5000 ppm (rabbit, 2 hr) [4]
6250 ppm (mouse, 2 hr) [4]
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
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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. [5]

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. [6]

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, 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. [5]

Like some other nitrated organic compounds, nitroethane is also used as a fuel additive and a precursor to rocket propellants.[ citation needed ]

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 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 phenethylamines, including medications such as Pervitin and the racemic compound Benzedrine [7] (amphetamine), used as an anorectic medicine for obesity. [8]

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. [9] Children have been poisoned by accidental ingestion of artificial nail remover. [10]

The LD50 for rats is reported as 1100 mg/kg. [11]

Related Research Articles

<span class="mw-page-title-main">Xylene</span> Organic compounds with the formula (CH3)2C6H4

In organic chemistry, xylene or xylol are any of three organic compounds with the formula (CH3)2C6H4. They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are substituted determines which of three structural isomers results. It is a colorless, flammable, slightly greasy liquid of great industrial value.

<span class="mw-page-title-main">Dimethylaniline</span> Chemical compound

N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.

Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula CH
3NO
2. It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent. As an intermediate in organic synthesis, it is used widely in the manufacture of pesticides, explosives, fibers, and coatings. Nitromethane is used as a fuel additive in various motorsports and hobbies, e.g. Top Fuel drag racing and miniature internal combustion engines in radio control, control line and free flight model aircraft.

<span class="mw-page-title-main">Nitro compound</span> Organic compound containing an −NO₂ group

In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups. The nitro group is one of the most common explosophores used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.

<span class="mw-page-title-main">Methylamine</span> Organic chemical compound

Methylamine, also known as methanamine, is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This flammable, colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">Methyl acetate</span> Chemical compound

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<span class="mw-page-title-main">Henry reaction</span> Chemical reaction

The Henry reaction is a classic carbon–carbon bond formation reaction in organic chemistry. Discovered in 1895 by the Belgian chemist Louis Henry (1834–1913), it is the combination of a nitroalkane and an aldehyde or ketone in the presence of a base to form β-nitro alcohols. This type of reaction is also referred to as a nitroaldol reaction. It is nearly analogous to the aldol reaction that had been discovered 23 years prior that couples two carbonyl compounds to form β-hydroxy carbonyl compounds known as "aldols". The Henry reaction is a useful technique in the area of organic chemistry due to the synthetic utility of its corresponding products, as they can be easily converted to other useful synthetic intermediates. These conversions include subsequent dehydration to yield nitroalkenes, oxidation of the secondary alcohol to yield α-nitro ketones, or reduction of the nitro group to yield β-amino alcohols.

Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted in small amounts by rice plantations. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Ethylenediamine</span> Chemical compound

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

<span class="mw-page-title-main">Thiophenol</span> Chemical compound

Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol. The chemical structures of thiophenol and its derivatives are analogous to phenols, where the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring in phenol is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, in the case of 'thiol' that the alcohol oxygen atom is replaced by a sulfur atom.

<span class="mw-page-title-main">1-Propanol</span> Primary alcohol compound

1-Propanol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. 1-Propanol is used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

<span class="mw-page-title-main">Crotonaldehyde</span> Chemical compound

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

<span class="mw-page-title-main">Phenyl-2-nitropropene</span> Chemical compound

1-Phenyl-2-nitropropene, or simply phenyl-2-nitropropene, or P2NP, as it is commonly referred to, is a chemical compound from the aromatic group of compounds, with the formula C9H9NO2. It is a light-yellow crystalline solid with a distinct smell. Phenyl-2-nitropropene is used in the pharmaceutical industry to manufacture the drug Adderall, an amphetamine mixture used to treat ADHD and narcolepsy. P2NP and other similar nitrostyrenes are also employed in the clandestine manufacture of drugs of the amphetamine class, and are listed as drug precursors in many countries.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

<span class="mw-page-title-main">Diethylethanolamine</span> Chemical compound

Diethylethanolamine (DEAE) is the organic compound with the molecular formula (C2H5)2NCH2CH2OH. A colorless liquid, is used as a precursor in the production of a variety of chemical commodities such as the local anesthetic procaine.

<span class="mw-page-title-main">1-Nitropropane</span> Chemical compound

1-Nitropropane (1-NP) is a solvent. It is a colorless liquid, an isomer of 2-nitropropane (2-NP), and classified as a nitro compound.

References

  1. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0453". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ Reich, Hans. "Bordwell pKa table: "Nitroalkanes"". University of Wisconsin Chemistry Department. Retrieved 17 January 2016.
  3. ↑ Matthews, Walter; et al. (1975). "Equilibrium acidities of carbon acids. VI. Establishment of an absolute scale of acidities in dimethyl sulfoxide solution". Journal of the American Chemical Society. 97 (24): 7006. doi:10.1021/ja00857a010.
  4. 1 2 "Nitroethane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. 1 2 Sheldon B. Markofsky “Nitro Compounds, Aliphatic” in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi : 10.1002/14356007.a17_401.
  6. ↑ Agrawal, Jai (2007). Organic Chemistry of Explosives. Chichester, England: John Wiley & Sons. pp. 7–10. ISBN   9780470029671.
  7. ↑ "2016 National Drug Assessment Summary" (PDF). Drug Administration. November 2016.
  8. ↑ "2016 National Drug Assessment Summary" (PDF). Drug Administration. November 2016.
  9. ↑ "Chemical Sampling Information Nitroethane." Retrieved February 9, 2007, from the website of the US Occupational Safety & Health Administration.
  10. ↑ Hornfeldt CS, Rabe WH (1994). "Nitroethane poisoning from an artificial fingernail remover". J. Toxicol. Clin. Toxicol. 32 (3): 321–4. doi:10.3109/15563659409017967. PMID   8007041.
  11. ↑ MSDS for nitroethane (revised October 3, 2005), as reported by Fisher Scientific.
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