2-Nitropropane

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2-Nitropropane
2-Nitropropane.svg
2-Nitropropane Ball and Stick.png
Names
IUPAC name
2-Nitropropane
Identifiers
3D model (JSmol)
Abbreviations 2-NP
ChEBI
ChemSpider
ECHA InfoCard 100.001.100
EC Number 201-209-1
Properties
C3H7NO2
Molar mass 89.09 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) 7.68
-45.73·10−6 cm3/mol
1.3944 (20 °C)
Viscosity 0.721 cP
Hazards
Main hazards Health hazard
GHS pictograms The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
H350
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
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]
US health exposure limits (NIOSH):
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 primarily as a solvent and chemical intermediate. It is used in inks, paints, adhesives, varnishes, polymers, resins, fuel, and coatings.[5]

2-Nitropropane is also used as a feedstock for other industrial chemicals.[5]

2-Nitropropane has uses in the synthesis of phentermine, chlorphentermine, as well as in the synthesis of teclozan, etc.

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 and 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: 14143–14148. doi:10.1039/c4ra00332b. 
  5. ^ a b c "Report on Carcinogens" (PDF) (Twelfth ed.). National Toxicology Program, Department of Health and Human Services. 2011. 
  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 3084482Freely accessible. PMID 21556207. 
  7. ^ Agents Classified by the IARC Monographs