2-Nitropropane

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2-Nitropropane
2-Nitropropane.svg
2-Nitropropane Ball and Stick.png
Names
IUPAC name
2-Nitropropane
Identifiers
79-46-9
3D model (Jmol) Interactive image
Abbreviations 2-NP
ChEBI CHEBI:16037
ChemSpider 387
ECHA InfoCard 100.001.100
EC Number 201-209-1
PubChem 398
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
NFPA 704
Flammability (red): no hazard code 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-NP is produced by the high-temperature vapor-phase nitration of propane, usually with impurities of 1-nitropropane. 2-NP is also produced as a volatile by-product that can be captured during Leonard's ring-closure hydantoin preparation [4]


Uses[edit]

2-NP is used primarily as a solvent and chemical intermediate. It is used in inks, paints, adhesives, varnishes, polymers, resins, fuel, and coatings.[5]

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

2-NP has uses in the synthesis of phentermine, chlorphentermine, as well as in the synthesis of Teclozan, etc.

Safety[edit]

Based on studies in animals, 2-NP is reasonably anticipated to be a human carcinogen[5] and it is listed as an IARC Group 2B carcinogen.[6]

References[edit]

  1. ^ a b Record in the GESTIS Substance Database of the IFA
  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. 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. ^ Agents Classified by the IARC Monographs