2-Nitropropane

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2-Nitropropane
2-Nitropropane.svg
2-Nitropropane Ball and Stick.png
Names
Preferred IUPAC name
2-Nitropropane
Identifiers
3D model (JSmol)
Abbreviations 2-NP
ChEBI
ChemSpider
ECHA InfoCard 100.001.100 Edit this at Wikidata
EC Number
  • 201-209-1
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
Appearance Colorless 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 GHS08: Health hazard
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.

Preparation[edit]

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[edit]

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[edit]

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]

References[edit]

  1. ^ a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0460". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b "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". RSC Advances. 4 (27): 14143–14148. doi:10.1039/c4ra00332b. S2CID 55586351.
  5. ^ a b c "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.