2-Nitropropane

Last updated
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
Main hazards Health hazard
GHS pictograms GHS-pictogram-silhouette.svg
H350
NFPA 704 (fire diamond)
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).
Infobox references

2-Nitropropane (2-NP) is a solvent. 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. [4]

Uses

2-Nitropropane is used as a solvent or additive in inks, paints, adhesives, varnishes, polymers, resins, fuel, and coatings. [5] It is also used as a feedstock for other industrial chemicals, [5] and also in the synthesis of pharmaceuticals such as phentermine, chlorphentermine, and teclozan. It serves as an oxidant in the Hass–Bender oxidation process.

Safety

2-Nitropropane is a constituent of tobacco smoke. [6] Based on studies in animals, it is reasonably anticipated to be a human carcinogen [5] and it is listed as an IARC Group 2B carcinogen. [7]

Related Research Articles

Carcinogen Substance, radionuclide, or radiation directly involved in causing cancer

A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis, the formation of cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substances are considered carcinogens, but their carcinogenic activity is attributed to the radiation, for example gamma rays and alpha particles, which they emit. Common examples of non-radioactive carcinogens are inhaled asbestos, certain dioxins, and tobacco smoke. Although the public generally associates carcinogenicity with synthetic chemicals, it is equally likely to arise in both natural and synthetic substances. Carcinogens are not necessarily immediately toxic; thus, their effect can be insidious.

Formaldehyde Widely used toxic organic compound

Formaldehyde ( fer-mal-duh-hahyd, alsofor-) (systematic name methanal) is a naturally occurring organic compound with the formula CH2O (H−CHO). The pure compound is a pungent-smelling colorless gas that polymerises spontaneously into paraformaldehyde (refer to section Forms below), hence it is stored as an aqueous solution (formalin). It is the simplest of the aldehydes (R−CHO). The common name of this substance comes from its similarity and relation to formic acid.

Butanone Chemical compound

Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless 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.

1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDB or para) is an organic compound 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.

Chloroethane Chemical compound commonly known as ethyl chloride

Chloroethane, commonly known as ethyl chloride, is a chemical compound with chemical formula CH3CH2Cl, once widely used in producing tetraethyllead, a gasoline additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet odor.

Acrylonitrile is an organic compound with the formula CH2CHCN. It is a colorless volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecular structure, it 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. Acrylonitrile was first synthesized by the French chemist Charles Moureu (1863–1929) in 1893.

Nitrobenzene Chemical compound

Nitrobenzene is an organic compound 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.

Bromoform Chemical compound

Bromoform (CHBr3) is a brominated organic solvent, colorless liquid at room temperature, with a high refractive index, very high density, and sweet odor is similar to that of chloroform. It is one of the four haloforms, the others being fluoroform, chloroform, and iodoform. Bromoform can be prepared by the haloform reaction using acetone and sodium hypobromite, by the electrolysis of potassium bromide in ethanol, or by treating chloroform with aluminium bromide. Currently its main use is as a laboratory reagent.

1,4-Dioxane Chemical compound

1,4-Dioxane is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers are rarely encountered.

Ethylbenzene Chemical compound

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 an 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.

<i>beta</i>-Propiolactone Chemical compound

β-Propiolactone is an organic compound of the lactone family, with a four-membered ring. It is a colorless liquid with a slightly sweet odor, highly soluble in water and miscible with ethanol, acetone, diethyl ether and chloroform. The word propiolactone usually refers to this compound, although it may also refer to α-propiolactone.

Nitroethane 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.

Glycidol Chemical compound

Glycidol is an organic compound that contains both epoxide and alcohol functional groups. Being bifunctional, it has a variety of industrial uses. The compound is a slightly viscous liquid that is slightly unstable and is not often encountered in pure form.

Vinyl fluoride Chemical compound

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

Vinyl bromide Chemical compound

Vinyl bromide is a simple vinyl halide. It is a colorless liquid. It is produced from ethylene dibromide. It is mainly used as a comonomer to confer fire retardant properties to acrylate polymers.

Chloromethyl methyl ether Chemical compound

Chloromethyl methyl ether (CMME) is a compound with formula CH3OCH2Cl. It is a chloroalkyl ether. It is used as an alkylating agent and industrial solvent to manufacture the detergent dodecylbenzyl chloride, water repellents and ion-exchange resins. In organic synthesis, it is used for introducing the methoxymethyl (MOM) protecting group, and is thus often called MOM-Cl or MOM chloride. It also finds application as a chloromethylating agent in some variants of the Blanc chloromethylation.

Hexachlorobutadiene Chemical compound

Hexachlorobutadiene, Cl2C=C(Cl)C(Cl)=CCl2, is a colorless liquid at room temperature that has an odor similar to that of turpentine. It is a chlorinated aliphatic diene with niche applications but is most commonly used as a solvent for other chlorine-containing compounds.

1,2-Dichloropropane Chemical compound

1,2-Dichloropropane is an organic compound classified as a chlorocarbon. It is a colorless, flammable liquid with a sweet odor. it is obtained as a byproduct of the production of epichlorohydrin, which is produced on a large scale.

1-Nitropropane 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.

Occupational cancer is cancer caused by occupational hazards. Several cancers have been directly tied to occupational hazards, including chimney sweeps' carcinoma, mesothelioma, and others.

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. 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.
  5. 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.
  6. 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.
  7. "Agents Classified by the IARC Monographs" (PDF). Archived from the original (PDF) on 2011-10-25. Retrieved 2012-06-13.