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2-Nitropropane

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This is an old revision of this page, as edited by Mjlphd (talk | contribs) at 09:00, 20 October 2016 (Added a sentence to the preparation section to describe an alternative way to make this compound. Added a peer-reviewed journal article reference that supports this claim.). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

2-Nitropropane
Names
IUPAC name
2-Nitropropane
Identifiers
3D model (JSmol)
Abbreviations 2-NP
ChEBI
ChemSpider
ECHA InfoCard 100.001.100 Edit this at Wikidata
EC Number
  • 201-209-1
  • 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
  • CC(C)[N+](=O)[O-]
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) 7.68
1.3944 (20 °C)
Viscosity 0.721 cP
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability (red): no hazard codeInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3
2
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]
NIOSH (US health exposure limits):
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).

2-Nitropropane (2-NP) is a solvent. It is a colorless liquid and is classified as a nitro compound.

Preparation

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

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

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

  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 or 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 and H. M. Hϋgel (6 Mar 2014). "Alternative synthesis of the anti-baldness compound RU58841". RSC Advances. 4: 14143–14148. doi:10.1039/c4ra00332b.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ a b c "Report on Carcinogens" (Document). National Toxicology Program, Department of Health and Human Services. 2011. {{cite document}}: Unknown parameter |edition= ignored (help); Unknown parameter |url= ignored (help)
  6. ^ Agents Classified by the IARC Monographs
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