2-Nitropropane

2-Nitropropane
Names
	Preferred IUPAC name 2-Nitropropane
Identifiers
CAS Number	79-46-9 ;
3D model (JSmol)	Interactive image;
Abbreviations	2-NP
ChEBI	CHEBI:16037;
ChemSpider	387;
ECHA InfoCard	100.001.100
EC Number	201-209-1;
PubChem CID	398;
UNII	GKV234L2QH ;
CompTox Dashboard (EPA)	DTXSID6020981 ;
	InChI 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;
	SMILES CC(C)[N+](=O)[O-];
Properties
Chemical formula	C3H7NO2
Molar mass	89.094 g·mol−1
Appearance	Colorless liquid
Odor	Pleasant, fruity
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)
Solubility in water	17 g/L
Solubility	soluble in chloroform
log P	0.93
Vapor pressure	13 mmHg (20°C)
Acidity (pKa)	16.9 (in DMSO)
Magnetic susceptibility (χ)	-45.73·10−6 cm3/mol
Refractive index (nD)	1.3944 (20 °C)
Viscosity	0.721 cP
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Health hazard
	GHS labelling:
Pictograms
Hazard statements	H350
NFPA 704 (fire diamond)	3 3 2
Flash point	24 °C (75 °F; 297 K) (open cup); 39 °C (closed cup)
Autoignition; temperature	428 °C (802 °F; 701 K)
Explosive limits	2.6-11.0%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	720 mg/kg
LC50 (median concentration)	2703 ppm (mouse, 2 hr); 400 ppm (rat, 6 hr)
LCLo (lowest published)	714 ppm (cat, 5 hr); 2381 ppm (rabbit, 5 hr); 4622 ppm (guinea pig, 5 hr); 2353 ppm (cat, 1 hr)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 25 ppm (90 mg/m3)
REL (Recommended)	Ca
IDLH (Immediate danger)	Ca [100 ppm]
	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 an organic compound with the formula (CH₃)₂CH(NO₂). It is used as a solvent.^[4] 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.^[5]

Uses

2-Nitropropane is used as a solvent or additive in inks, paints, adhesives, varnishes, polymers, resins, fuel, and coatings.^[6] It is also used as a feedstock for other industrial chemicals,^[6] 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.^[7] Based on studies in animals, it is reasonably anticipated to be a human carcinogen^[6] and it is listed as an IARC Group 2B carcinogen.^[8]

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).
^ Markofsky, S. B. (2000). "Nitro Compounds, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_401.pub2. ISBN 978-3527306732.
^ 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.

[GESTIS-1] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[PGCH-2] ^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0460". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-3] "2-Nitropropane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Markofsky-4] Markofsky, S. B. (2000). "Nitro Compounds, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_401.pub2. ISBN 978-3527306732.

[Leonard-5] 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.

[NIH-6] "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.

[TalhoutSchulz2011-7] 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.

[8] "Agents Classified by the IARC Monographs" (PDF). Archived from the original (PDF) on 2011-10-25. Retrieved 2012-06-13.

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