| Identification | More | [Name]
2-Nitropropane | [CAS]
79-46-9 | [Synonyms]
2-NITROPROPANE
2-NP
BETA-NITROPROPANE
ISONITROPROPANE
NITROISOPROPANE
sec-Nitropropane
2-nitro-propan
b-nitropropane
Dimethylnitromethane
i-C3H7NO2
Nipar S-20
Nipar S-20 solvent
Nipar S-30 solvent
nipars-20
nipars-20solvent
nipars-30solvent
Propane,2-nitro-
Rcra waste number U171
rcrawastenumberu171
2-Nitropropane,97% | [EINECS(EC#)]
201-209-1 | [Molecular Formula]
C3H7NO2 | [MDL Number]
MFCD00007397 | [Molecular Weight]
89.09 | [MOL File]
79-46-9.mol |
| Chemical Properties | Back Directory | [Description]
2-Nitropropane (2-NP) is a clear colourless liquid with a pleasant odour. 2-NP is soluble in many organic solvents including chloroform. Its vapours may form an explosive mixture with air. 2-NP is primarily used as a solvent for organic compounds, coatings, inks, dyes, adhesives, and vinyl resins. Application of 2-NP improves drying time, insures more complete solvent release, provides better flow characteristics, and insures greater pigment dispersion (1,2,3,5). 2-NP has a minor use as an additive in explosives, propellants, and fuels (in racing cars). It also has limited use as a paint and varnish remover. 2-NP serves as an intermediate in the synthesis of some pharmaceuticals, dyes, insecticides, and textile chemicals. It is used for coatings as with vinyl, epoxy paints, nitrocellulose, and chlorinated rubber, in printing inks, adhesives, printing as flexographic inks, maintenance with traffic markings on roads and highways, shipbuilding and maintenance, in furniture, and plastic industries. 2-NP is also used as a solvent in food processing industries for fractionation of a partially saturated vegetable oil. Because of its large-scale use pattern, human exposure to 2-NP has become a health concern. | [Definition]
A solvent. | [Appearance]
2-Nitropropane is a colorless liquid. | [Melting point ]
-93 °C | [Boiling point ]
120 °C(lit.)
| [density ]
0.992 g/mL at 25 °C(lit.)
| [vapor density ]
~3 (vs air)
| [vapor pressure ]
~13 mm Hg ( 20 °C)
| [refractive index ]
n20/D 1.394(lit.)
| [Fp ]
99 °F
| [storage temp. ]
Flammables area | [solubility ]
H2O: slightly soluble | [form ]
Liquid | [pka]
pK1:7.675 (25°C) | [color ]
Colorless to Almost colorless | [Stability:]
Stable. Incompatible with strong oxidizing agents, strong bases, copper. | [Water Solubility ]
1.7 g/100 mL (20 ºC) | [Merck ]
6628 | [BRN ]
1740684 | [Henry's Law Constant]
8.92 at 20.00 °C, 15.3 at 30.00 °C, 24.4 at 40.00 °C, 36.9 at 50.00 °C (inert gas stripping, Bene?
and Dohnal, 1999) | [Dielectric constant]
25.5 | [Exposure limits]
Potential occupational carcinogen. NIOSH REL: IDLH 100 ppm; OSHA PEL:
TWA 25 ppm (90 mg/m3); ACGIH TLV: TWA 10 ppm (adopted). | [LogP]
1.35 at 20℃ | [Uses]
Solvent (especially for vinyl and epoxy coatings), chemical synthesis, rocket propellant, gasoline additive. | [CAS DataBase Reference]
79-46-9(CAS DataBase Reference) | [IARC]
2B (Vol. 29, Sup 7, 71) 1999 | [NIST Chemistry Reference]
Propane, 2-nitro-(79-46-9) | [EPA Substance Registry System]
79-46-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R45:May cause cancer.
R10:Flammable.
R20/22:Harmful by inhalation and if swallowed . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2608 3/PG 3
| [WGK Germany ]
3
| [RTECS ]
TZ5250000
| [Autoignition Temperature]
802 °F | [HazardClass ]
3.2 | [PackingGroup ]
III | [HS Code ]
29042000 | [Safety Profile]
Confirmed carcinogen
with experimental carcinogenic,
tumorigenic, and teratogenic data. Poison by
intraperitoneal route. Moderately toxic by
ingestion and inhalation. Human systemic
effects by inhalation: anorexia, hypermothty,
diarrhea, nausea or vomiting. An experimental
teratogen. Other experimental
reproductive effects. Mutation data reported.
Can cause liver and kidney injury,
methemoglobinemia, and cyanosis. Very
dangerous fire hazard when exposed to heat,
open flame, or oxidizers. May explode on
heating. Violent reactions with chlorosulfonic
acid, oleum. May react with amines +
heavy metal oxides (e.g., mercury oxide or
silver oxide) to form explosive salts. May
ignite on contact with mixtures of carbon +
hopcalite, whch are used in some respirators.
Hopcalite is a catalyst consisting of
coprecipitated copper(Ⅱ) oxide and
manganese0 oxide. To fight fire, use
alcohol foam, CO2, dry chemical, water
spray. When heated to decomposition it
emits toxic fumes of NOx. | [Hazardous Substances Data]
79-46-9(Hazardous Substances Data) | [Toxicity]
Acute oral LD50 for rats 720 mg/kg (quoted, RTECS, 1985). | [IDLA]
100 ppm |
| Hazard Information | Back Directory | [General Description]
Colorless liquid with a mild fruity odor. May float on or sink in water. | [Reactivity Profile]
2-NITROPROPANE(79-46-9) is sensitive to heat. Can react with amines/heavy metal oxides, strong acids, strong alkalis, and chlorosulfonic acid. . The heat of adsorption of this compound on carbon, such as that found in cartridge respirators, is extremely high. Metal oxide catalysts, such as copper oxide or manganese oxide, can initiate ignition, therefore carbon respirators should not be used in environments that have a high vapor concentration of this material. | [Air & Water Reactions]
Highly flammable. | [Hazard]
Flammable, dangerous fire risk, moderate
explosion hazard when shocked or heated. Liver
damage and liver cancer. Possible carcinogen. | [Health Hazard]
Inhalation causes respiratory tract irritation, headache, dizziness, nausea, and diarrhea. Ingestion causes irritation of mouth and stomach. Contact with liquid irritates eyes and causes mild irritation of skin. | [Potential Exposure]
2-Nitropropane is used as a solvent
for polymers, organic compounds; cellulose, esters; gums,vinyl resins; waxes, epoxy resins, fats, dyes, and chlorinated
rubber; as a stabilizer. Its combustion properties have
made it useful as a rocket propellant and as a gasoline and
diesel fuel additive. 2-Nitropropane also has limited use as
a paint and varnish remover. It serves as an intermediate in
organic synthesis of some pharmaceuticals; dyes, insecticides,
and textile chemicals. | [Fire Hazard]
Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including
resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical
attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
| [Shipping]
UN2608 Nitropropanes, Hazard Class: 3; Labels:
3-Flammable liquid. | [Incompatibilities]
1-Nitropropane, a nitroparaffin compound,
forms explosive mixture with air. Contact with
heavy metal oxides may cause decomposition. Mixtures
with hydrocarbons are extremely flammable. Attacks
some plastics, rubber and coatings. May explode on heating.
Violent reaction with strong bases; strong acids and
metal oxides. Shock-sensitive compounds are formed
with acids, amines, inorganic bases and heavy metal
oxides. Incompatible with strong oxidizers, combustible
materials. 2-Nitropropane reacts with activated carbon
causing decomposition. This reaction may occur in
activated carbon respirator filters. | [Chemical Properties]
2-Nitropropane exists in equilibrium with 2-propane nitronic acid (HSDB 1988).
A 0.01 M aqueous solution has a pH of 6.2. 2-Nitropropane reacts with inorganic
bases and amines to form salts which are flammable when dry. 2-Nitropropane is
sensitive to detonation when mixed with oxidizers and a mixture of the chemical
with ammonium nitrate is a commercial explosive. | [Chemical Properties]
2-Nitropropane(2-NP) is an aliphatic nitro compound. It is a colorless, oily, and flammable liquid with a mild fruity odor. Soluble in water 1.7 mL/100 mL (20C); solubility of water in 2-nitropropane 0.6 cc/100 cc (20C); miscible with organic solvents.
As other nitroalkane, 2-NP exists in tautomeric equilibrium with its nitronic acid isomers (protonated and anionic aci forms).The aci form is amphoterically reactive, the protonated form being electrophilic and the anionic form being nucleophilic. | [Waste Disposal]
Incineration: large quantities
of material may require nitrogen oxide removal by catalytic
or scrubbing processes. Dilute with pure kerosene and
burn with care as it is potentially explosive. Consult with
environmental regulatory agencies for guidance on
acceptable disposal practices. Generators of waste containing
this contaminant (≥100 kg/mo) must conform with
EPA regulations governing storage, transportation, treatment,
and waste disposal. | [Physical properties]
Colorless, oily liquid with a mild, fruity odor. 2-Nitropropane was detected in two studies at
concentrations of 3.1 and 5.2 ppmv (Crawford et al., 1984). | [Preparation]
The synthesis of 2-nitropropane can be accomplished directly by nitration of 2-halopropanes with sodium nitrite. With 2-iodopropane, the reaction is carried out in dry DMF in the presence of urea. For the slower reacting 2-bromopropane, a longer reaction time and the presence of phloroglucinol as a nitrite ester scavenger is required.
Like 1-nitropropane, 2-nitropropane is also produced by vapor-phase nitration of propane with nitric acid at elevated temperature and pressure (Baker and Bollmeier 1978). | [Production Methods]
Like 1-nitropropane, 2-nitropropane is produced by vapor-phase nitration of
propane with nitric acid at elevated temperature and pressure (Baker and Bollmeier
1978). U.S. production in 1977 was put at 30 million pounds (Finklea 1977).
Amounts in use have been greatly reduced in recent times because of concern
about its carcinogenic potential. | [Industrial uses]
Solvent systems containing 2-nitropropane are used in various coatings, including
vinyl, epoxy paints, nitrocellulose and chlorinated rubber, printing inks and
adhesives. When mixed with oxidizers, it is used in explosives (HSDB 1988). | [Carcinogenicity]
2-Nitropropane is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals. | [Environmental Fate]
Photolytic. Anticipated products from the reaction of 2-nitropropane with ozone or OH radicals
in the atmosphere are formaldehyde and acetaldehyde (Cupitt, 1980). | [Metabolism]
After exposure of male Sprague-Dawley rats to 2-nitropropane (200 p.p.m. by
inhalation, or 50 mg/kg intraperitoneally) the major pathway of elimination was by
exhalation. Carbon dioxide, acetone and isopropanol were the major metabolites.
Exhalation was also the major route of elimination after a dose of 10 mg/kg to
chimpanzees (Muller et al 1983). Nonlinear elimination of 2-nitropropane was
suggested by studies in which male Sprague-Dawley rats were exposed by
inhalation to doses of 20 or 154 p.p.m. radiolabeled 2-nitropropane for 6 h (Nolan
et al 1982). Average blood 2-nitropropane concentrations immediately following
the 20 and 154 p.p.m. exposures were 0.6 and 7.1 μg/ml, respectively. Furthermore,
raising the dose from 20 to 154 p.p.m. caused a greater fraction of the
radioactivity to be excreted as unchanged 2-nitropropane. The dose-dependent
changes in the elimination of 2-nitropropane may account, at least in part, for the
increase in toxicity observed in rats exposed to large concentrations of 2-nitropropane
(Lewis et al 1979).
Analysis of incubations of 2-nitropropane with liver microsomes of phenobarbital
or 3-methylcholanthrene pretreated male Sprague-Dawley rats indicated that
oxidative denitrification of 2-nitropropane produced acetone and nitrite (Ullrich et
al 1978). This effect seems not to be dependent on pretreatment with a cytochrome
P-450 inducer in other species or strains, since the hepatic microsomes from 5
strains of untreated mice all showed significant, but variable, NADPH-dependent
ability to release nitrite from 2-nitropropane (Marker and Kulkarni 1985). Ullrich
and coworkers (1978) considered that the reduction of the nitro group of 2-nitropropane
to form 2-aminopropane was unlikely, at least in vitro, since the rate of
oxidative denitrification of 2-nitropropane was unaltered in microsomal incubations
under reduced oxygen tension. Whether any significant nitro group reduction
of 2-nitropropane occurs in vivo to produce potentially reactive metabolites is
unknown. Speck et al (1982), however, have shown that 2-aminopropane is not
mutagenic in Salmonella tester strains. | [Purification Methods]
Purify it as for nitromethane. [Beilstein 1 IV 230.] | [Toxicity evaluation]
DNA damage can cause 2-NP metabolites such as N-isopropyl
hydroxylamine (IPHA) and hydroxylamine-O-sulfonic (HAS)
acid by a reactive oxygen generating process that can be inhibited
by free hydroxyl radical scavengers, catalase, and deferoxamine
mesylate, an iron chelating agent. IPHA causes DNA damage at
thymine and HAS most frequently induces DNA damage at
5'-TG-3', 5'-GG-3', and 5'
-GGG-3' sequences. Formation of
8-oxodesoxyguanine by IPHA or HAS increased in the presence
of metal ions.DNA damage caused by 2-NP metabolites plays an
important role in mutagenicity and carcinogenicity of 2-NP. The
liver damage induced by 2-NP is related to oxidative damage and
reduction in catalase (CAT) activity. |
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