2-Nitropropane

Last updated
2-Nitropropane
2-Nitropropane.svg
2-Nitropropane Ball and Stick.png
Names
Preferred IUPAC name
2-Nitropropane
Identifiers
3D model (JSmol)
Abbreviations2-NP
ChEBI
ChemSpider
ECHA InfoCard 100.001.100 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-209-1
PubChem CID
UNII
  • InChI=1S/C3H7NO2/c1-3(2)4(5)6/h3H,1-2H3
    Key: FGLBSLMDCBOPQK-UHFFFAOYSA-N
  • InChI=1/C3H7NO2/c1-3(2)4(5)6/h3H,1-2H3
    Key: FGLBSLMDCBOPQK-UHFFFAOYAM
  • CC(C)[N+](=O)[O-]
Properties
C3H7NO2
Molar mass 89.094 g·mol−1
AppearanceColorless liquid [1]
Odor Pleasant, fruity [2]
Density 0.9821 g/cm3
Melting point −91.3 °C (−132.3 °F; 181.8 K)
Boiling point 120.2 °C (248.4 °F; 393.3 K)
17 g/L [1]
Solubility soluble in chloroform
log P 0.93
Vapor pressure 13 mmHg (20°C) [2]
Acidity (pKa)16.9 (in DMSO)
-45.73·10−6 cm3/mol
1.3944 (20 °C)
Viscosity 0.721 cP
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Health hazard
GHS labelling:
GHS-pictogram-silhouette.svg
H350
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3
3
2
Flash point 24 °C (75 °F; 297 K) (open cup)
39 °C (closed cup)
428 °C (802 °F; 701 K)
Explosive limits 2.6-11.0% [2]
Lethal dose or concentration (LD, LC):
720 mg/kg
2703 ppm (mouse, 2 hr)
400 ppm (rat, 6 hr) [3]
714 ppm (cat, 5 hr)
2381 ppm (rabbit, 5 hr)
4622 ppm (guinea pig, 5 hr)
2353 ppm (cat, 1 hr) [3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 25 ppm (90 mg/m3) [2]
REL (Recommended)
Ca [2]
IDLH (Immediate danger)
Ca [100 ppm] [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Nitropropane (2-NP) is an organic compound with the formula (CH3)2CH(NO2). It is used as a solvent. [4] It is a colorless liquid and is classified as a nitro compound.

Contents

Preparation

2-Nitropropane is produced by the high-temperature vapor-phase nitration of propane, usually with impurities of 1-nitropropane. 2-Nitropropane is also produced as a volatile by-product that can be captured during Leonard's ring-closure hydantoin preparation. [5]

Uses

2-Nitropropane is used as a solvent or additive in inks, paints, adhesives, varnishes, polymers, resins, fuel, and coatings. [6] It is also used as a feedstock for other industrial chemicals, [6] It serves as an oxidant in the Hass–Bender oxidation process.

Drugs List

Also used in the synthesis of pharmaceuticals such as:

  1. Bucindolol
  2. Chlorphentermine
  3. Clortermine
  4. D-380 [1081-78-3]
  5. Mephentermine & thus Oxetacaine.
  6. Phentermine
  7. Teclozan

Safety

2-Nitropropane is a constituent of tobacco smoke. [7] Based on studies in animals, it is reasonably anticipated to be a human carcinogen [6] and it is listed as an IARC Group 2B carcinogen. [8]

Related Research Articles

<span class="mw-page-title-main">Carcinogen</span> Substance, radionuclide, or radiation directly involved in causing cancer

A carcinogen is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruses and bacteria. Most carcinogens act by creating mutations in DNA that disrupt a cell's normal processes for regulating growth, leading to uncontrolled cellular proliferation. This occurs when the cell's DNA repair processes fail to identify DNA damage allowing the defect to be passed down to daughter cells. The damage accumulates over time. This is typically a multi-step process during which the regulatory mechanisms within the cell are gradually dismantled allowing for unchecked cellular division.

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

Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

<span class="mw-page-title-main">1,4-Dichlorobenzene</span> Chemical compound

1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDCB or para) is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring.

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.

Acrylonitrile is an organic compound with the formula CH2CHCN and the structure H2C=CH−C≡N. It is a colorless, volatile liquid. It has a pungent odor of garlic or onions. Its molecular structure consists of a vinyl group linked to a nitrile. It is an important monomer for the manufacture of useful plastics such as polyacrylonitrile. It is reactive and toxic at low doses.

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

Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents.

<span class="mw-page-title-main">Chemical hazard</span> Non-biological hazards of hazardous materials

Chemical hazards are hazards present in hazardous chemicals and hazardous materials. Exposure to certain chemicals can cause acute or long-term adverse health effects. Chemical hazards are usually classified separately from biological hazards (biohazards). Chemical hazards are classified into groups that include asphyxiants, corrosives, irritants, sensitizers, carcinogens, mutagens, teratogens, reactants, and flammables. In the workplace, exposure to chemical hazards is a type of occupational hazard. The use of personal protective equipment may substantially reduce the risk of adverse health effects from contact with hazardous materials.

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

Bromoform is an organic compound with the chemical formula CHBr3. It is a colorless liquid at room temperature, with a high refractive index and a very high density. Its sweet odor is similar to that of chloroform. It is one of the four haloforms, the others being fluoroform, chloroform, and iodoform. It is a brominated organic solvent. Currently its main use is as a laboratory reagent. It is very slightly soluble in water and is miscible with alcohol, benzene, chloroform, ether, petroleum ether, acetone and oils.

<span class="mw-page-title-main">Ethylbenzene</span> Hydrocarbon compound; precursor to styrene and polystyrene

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

β-Propiolactone Chemical compound

β-Propiolactone, often simply called propiolactone, is an organic compound with the formula CH2CH2CO2. It is a lactone family, with a four-membered ring. It is a colorless liquid with a slightly sweet odor, highly soluble in water and organic solvents. The carcinogenicity of this compound has limited its commercial applications.

<span class="mw-page-title-main">1,2-Dichlorobenzene</span> Chemical compound

1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.

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

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.

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

Glycidol is an organic compound with the formula HOCH2CHOCH2. The molecule contains both epoxide and alcohol functional groups. Being simple to make and bifunctional, it has a variety of industrial uses. The compound is a colorless, slightly viscous liquid that is slightly unstable and is not often encountered in pure form.

<span class="mw-page-title-main">1,3-Dichloropropene</span> Chemical compound

1,3-Dichloropropene, sold under diverse trade names, is an organochlorine compound with the formula C3H4Cl2. It is a colorless liquid with a sweet smell. It is feebly soluble in water and evaporates easily. It is used mainly in farming as a pesticide, specifically as a preplant fumigant and nematicide. It is widely used in the US and other countries, but is banned in 34 countries.

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

Vinyl fluoride is an organic halide with the chemical formula C2H3F. It is a colorless gas with a faint ether-like odor. It is used as the monomeric precursor to the fluoropolymer polyvinylfluoride.

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

Vinyl bromide is the organobromine compound with the formula CH2=CHBr. Classified as a vinyl halide, it is a colorless gas at room temperature. It is used as a reagent and a comonomer.

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

1-Bromopropane (n-propylbromide or nPB) is an organobromine compound with the chemical formula CH3CH2CH2Br. It is a colorless liquid that is used as a solvent. It has a characteristic hydrocarbon odor. Its industrial applications increased dramatically in the 21st century due to the phasing out of chloro­fluoro­carbons and chloro­alkanes such as 1,1,1-Trichloro­ethane under the Montreal Protocol.

<i>o</i>-Anisidine Chemical compound

o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

<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 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0460". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 "2-Nitropropane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ Markofsky, S. B. (2000). "Nitro Compounds, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_401.pub2. ISBN   978-3527306732.
  5. ↑ M. J. Leonard; A. R. Lingham; J. O. Niere; N. R. C. Jackson; P. G. McKay; H. M. Hϋgel (6 Mar 2014). "Alternative synthesis of the anti-baldness compound RU58841" (PDF). RSC Advances. 4 (27): 14143–14148. Bibcode:2014RSCAd...414143L. doi:10.1039/c4ra00332b. S2CID   55586351.
  6. 1 2 3 "2-Nitropropane". Report on Carcinogens (PDF) (Report) (Twelfth ed.). National Toxicology Program, Department of Health and Human Services. 2011. p. 300. Archived from the original (PDF) on 2012-01-20. Retrieved 2012-06-13.
  7. ↑ Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". International Journal of Environmental Research and Public Health. 8 (12): 613–628. doi: 10.3390/ijerph8020613 . ISSN   1660-4601. PMC   3084482 . PMID   21556207.
  8. ↑ "Agents Classified by the IARC Monographs" (PDF). Archived from the original (PDF) on 2011-10-25. Retrieved 2012-06-13.
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