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2-Nitropropane
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2-Nitropropane.svg 150px skin-invert 2-Nitropropane Ball and Stick.png bg-transparent 200 2-Nitropropane 2-NPINPi-PrNO2iPrNO2iPrNO2 79-46-9 correct CAS correct FDA GKV234L2QH 398 387 201-209-1 16037 CC(C)[N+](=O)[O-] 1/C3H7NO2/c1-3(2)4(5)6/h3H,1-2H3 FGLBSLMDCBOPQK-UHFFFAOYAM 1S/C3H7NO2/c1-3(2)4(5)6/h3H,1-2H3 FGLBSLMDCBOPQK-UHFFFAOYSA-N
3 7 1 2 Colorless liquid22410 Pleasant, fruity0460 0.9821 g/cm3 -91.3 120.2 17 g/L soluble in chloroform 16.9 (in DMSO) 0.93 1.3944 (20 °C) 0.721 cP 13 mmHg (20°C) −45.73·10−6 cm3/mol
Health hazard 02 07 08 226 302 332 350 203 210 233 240 241 242 243 261 264 270 271 280 301+317 303+361+353 304+340 317 318 330 370+378 403+235 405 501 24 (open cup)39 °C (closed cup) 428 2.6–11.0% 3 2 3 W 720 mg/kg TWA 25 ppm (90 mg/m3) Ca Ca [100 ppm] 2703 ppm (mouse, 2 hr)400 ppm (rat, 6 hr)79469 2-Nitropropane 714 ppm (cat, 5 hr)2381 ppm (rabbit, 5 hr)4622 ppm (guinea pig, 5 hr)2353 ppm (cat, 1 hr)
2-Nitropropane (2-NP) is an organic compound with the formula (CH3)2CH(NO2). It is used as a solvent. Markofsky, S. B. Nitro Compounds, Aliphatic Ullmann's Encyclopedia of Industrial Chemistry 2000 Wiley-VCH Weinheim 10.1002/14356007.a17_401.pub2 978-3527306732 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. Alternative synthesis of the anti-baldness compound RU58841 M. J. Leonard A. R. Lingham J. O. Niere N. R. C. Jackson P. G. McKay H. M. Hϋgel 55586351 RSC Advances 6 Mar 2014 4 27 14143–14148 10.1039/c4ra00332b 2014RSCAd...414143L http://www.mjlphd.net/uploads/2/4/4/0/24404036/alternative_synthesis_of_the_anti-baldness_compound_ru58841.pdf
Uses
2-Nitropropane is used as a solvent or additive in inks, paints, adhesives, varnishes, polymers, resins, fuel, and coatings.http://ntp.niehs.nih.gov/ntp/roc/twelfth/profiles/Nitropropane.pdf 2-Nitropropane Report on Carcinogens Twelfth 2011 300 National Toxicology Program, Department of Health and Human Services 2012-06-13 https://web.archive.org/web/20120120103345/http://ntp.niehs.nih.gov/ntp/roc/twelfth/profiles/Nitropropane.pdf 2012-01-20 It is also used as a feedstock for other industrial chemicals, 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.Talhout Reinskje Schulz Thomas Florek Ewa Van Benthem Jan Wester Piet Opperhuizen Antoon Hazardous Compounds in Tobacco Smoke International Journal of Environmental Research and Public Health 8 12 2011 613–628 1660-4601 10.3390/ijerph8020613 21556207 3084482 free Based on studies in animals, it is reasonably anticipated to be a human carcinogen and it is listed as an IARC Group 2B carcinogen.http://monographs.iarc.fr/ENG/Classification/ClassificationsGroupOrder.pdf Agents Classified by the IARC Monographs 2012-06-13 https://web.archive.org/web/20111025122327/http://monographs.iarc.fr/ENG/Classification/ClassificationsGroupOrder.pdf 2011-10-25 dead
References
Category:Nitroalkanes
Category:Nitro solvents
Category:Isopropyl compounds