2-Nitropropane
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| Names | |
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| Preferred IUPAC name
2-Nitropropane | |
| Identifiers | |
3D model (JSmol)
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| Abbreviations | 2-NP |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.001.100 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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 | |
Refractive index (nD)
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1.3944 (20 °C) |
| Viscosity | 0.721 cP |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Health hazard |
| GHS labelling: | |
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| H350 | |
| NFPA 704 (fire 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): | |
LD50 (median dose)
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720 mg/kg |
LC50 (median concentration)
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2703 ppm (mouse, 2 hr) 400 ppm (rat, 6 hr)[3] |
LCLo (lowest published)
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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)
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TWA 25 ppm (90 mg/m3)[2] |
REL (Recommended)
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Ca[2] |
IDLH (Immediate danger)
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Ca [100 ppm][2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Nitropropane (2-NP) is a solvent. It is a colorless liquid and is classified as a nitro compound.
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]
References
- ^ a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0460". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "2-Nitropropane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "Agents Classified by the IARC Monographs" (PDF). Archived from the original (PDF) on 2011-10-25. Retrieved 2012-06-13.