2-ニトロプロパン

Hazardous Air Pollutants (HAPs)

Nitrogen Compounds -> Nitros, Aliphatic

Carcinogens

Volatile Organic Compound (VOC)

log Kow = 0.93

0.93

0.8

0.99 at 68 °F (USCG, 1999) - Less dense than water; will float

0.9821 g/cu cm at 25 °C

Relative density (water = 1): 0.99

0.99

0.9821 @25 °C

0.99

greater than or equal to 0.1 mg/mL at 66 °F (NTP, 1992)

Soluble in chloroform

Miscible with most aromatic hydrocarbons, ketones, esters, ethers, and the lower carboxylic acids

In water, 1.70X10+4 mg/L at 25 °C

Solubility in water, g/100ml at 25 °C: 1.7

2%

75 °F (NTP, 1992)

75 °F

24 °C (75 °F)(closed cup)

39 °C (closed cup), 24 °C (open cup)

38 °C (open cup) /from table/

24 °C c.c.

248.5 °F at 760 mmHg (NTP, 1992)

120.2 °C

120 °C

249 °F

120.2 °C @760 [mm Hg]

249 °F

When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

May decompose explosively under fire conditions. /nitropropanes/

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P318, P330, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P317, P303+P361+P353, P304+P340, P316, P317, P318, P321, P330, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Chemical: Propane, 2-nitro-

Hazard Traits - Carcinogenicity; Hepatotoxicity and Digestive System Toxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity

Propane, 2-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 2-nitro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 26-11-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/12799

Propane, 2-nitro-: HSNO Approval: HSR001207 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire. (USCG, 1999)

Flammable. Many reactions may cause fire or explosion. Gives off irritating or toxic fumes (or gases) in a fire. Above 24 °C explosive vapour/air mixtures may be formed.

2-Nitropropane is used primarily as a solvent. Severe liver damage, as well as some kidney damage, has been observed in workers poisoned from acute (short-term) inhalation exposure to 2-nitropropane. Chronic (long-term) inhalation exposure to 2-nitropropane has caused nausea, vomiting, diarrhea, severe headaches, and pulmonary irritation in workers. Liver effects have been observed in animals chronically exposed to 2-nitropropane by inhalation. No information is available on the reproductive, developmental, or carcinogenic effects of 2-nitropropane in humans. In one animal study, liver tumors were observed in rats. EPA has classified 2-nitropropane as a Group B2, probable human carcinogen.

Acute liver injury and/or death have been reported in workers 1) painting the interior of a tank, 2) working in confined spaces with paint and polyester-based resin products, and 3) painting epoxy resins on walls. NP-2 induces methemoglobinemia of 15-25% in cats exposed at 280 ppm for 7 hours. Listed in the table Examples of Industrial Chemicals for Which Methemoglobin Formation is NOT the Principal Cause of Toxicity; [ACGIH] A skin, eye, and respiratory tract irritant; Inhalation of high concentrations may cause CNS effects; Exposure above the OEL could cause liver injury and death; [ICSC]

Fire Extinguishing Agents Not to Be Used: "Alcohol" foam; water may be ineffective.

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.

Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

(General first aid procedures)

Use water spray, dry chemical, foam, or carbon dioxide. Use water spray to keep fire exposed containers cool. Fight fire from protected location or maximum possible distance. /nitropropanes/

Alcohol foam and water may be ineffective.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Nitropropanes/

Store in a cool, dry, well ventilated location. Separate from amines, alkalies, acids, oxidizing materials, metal oxides, and combustibles. Outside or detached storage is preferred /nitropropanes/

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen and date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

After covering the spills with soda ash, mix and spray with water. Scoop into a bucket of water and leave it stand for two hours. Neutralize with 6M-hydrochloric acid and pass into drain with sufficient water.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured and the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed and labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /nitropropanes/

Environmental consideration: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /nitropropanes/

Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /nitropropanes/

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste numbers U171 and F005, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Nitropropane is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. Large quantities of material may require nitrogen oxide removal by catalytic or scrubbing process. /Nitropropane/

A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

For more Disposal Methods (Complete) data for 2-NITROPROPANE (9 total), please visit the HSDB record page.

Evacuate danger area! Consult an expert! Personal protection: self-contained breathing apparatus. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

/Use/ barrier creams...to protect exposed skin. ...

Remove contaminated clothing and shoes.

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food and beverage containers or utensils, and the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, and rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes and wear protective suits (preferably disposable, one-piece and close-fitting at ankles and wrists), gloves, hair covering and overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves and gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, and disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/

For more Preventive Measures (Complete) data for 2-NITROPROPANE (17 total), please visit the HSDB record page.

Eleven percent of samples of expired air from a carefully selected urban population of 54 normal, healthy, non-smoking individuals (387 samples) contained 2-nitropropane with a geometric mean concn of 0.406 ng/L(1).

/After occupational expossure/ one of the survivors had a 2-NP serum concentration of 8.5 mg/L when hospitalized. ... his coworker hospitalized at the same time with a serum concentration of 13 mg/L subsequently died, ...

The effect of diphenyl diselenide, (PhSe)2, administration on 2-nitropropane (2-NP)-induced hepatic damage was examined in male rats. Rats were pre-treated with a single dose of diphenyl diselenide (10, 50 or 100 micromol/kg). Afterward, they received only one dose of 2-NP (100 mg/kg bw dissolved in olive oil). The parameters that indicate tissue damage such as plasma alanine aminotransferase (ALT), aspartate aminotransferase (AST), gamma-glutamyl transferase (GGT), alpha-fetoprotein (AFP), creatinine and urea were determined. Since toxicity induced by 2-NP is related to oxidative stress, lipid peroxidation was also evaluated. Diphenyl diselenide (100 micromol/kg) significantly reduced plasma ALT, gamma-GGT, AFP levels when compared to 2-NP group. Treatment with diphenyl diselenide, at all doses, effectively protects the increase of lipid peroxidation when compared to 2-NP group. Histological examination revealed that 2-NP treatment causes a moderate swelling and degenerative alterations on hepatocytes and diphenyl diselenide (100 micromol/kg) protects against these alterations. Diphenyl diselenide (50 and 100 micromol/kg) significantly decreased the urea level. This study evidences the protective effect of diphenyl diselenide by 2-NP-induced acute hepatic damage.

...Three groups of male rats (control, 2-NP-treated [4 mmol/kg] and 2-NP + melatonin [10 mg/kg]) were used in the current study. Cell proliferation was quantitated by incorporation of 3H-thymidine, detected by autoradiography, into newly synthesized DNA. Histopatholgical study was carried out to investigate the morphological changes. Twenty four hours after 2-NP administration, there was an increase in the labelling index (LI) and grain count per labelled nucleus (GC/N) in the hepatocytes of 2-NP-injected rats versus those of control animals. The increase was 69.5% in LI and 29.4% in GC/N. Melatonin treatment, 30 minutes preceding 2-NP, reduced the increase in LI (44.4%) and GC/N (20.7%) when compared with 2-NP-treated rats. Histopathology revealed multiple focal areas of necrosis in the liver following 2-NP injection. In the lung, there was a mucinous degeneration of the bronchial epithelium. Melatonin treatment restored the histopathological changes in both the liver and lung and they are more or less normal.

Hepatic

Eyes, skin, respiratory system, central nervous system, kidneys, liver

LC50 Pimephales promelas (fathead minnow) 4.71 mg/L/96 hr (confidence limit 4.46 - 4.98 mg/L), flow-through bioassay with measured concentrations, 26.0 °C, dissolved oxygen 6.9 mg/L, hardness 44.3 mg/l calcium carbonate, alkalinity 44.2 mg/L calcium carbonate, and pH 7.8.

LC50 Brachydanio rerio (Zebrafish) 620 mg/L/48 hr; closed system, static

EC50 Scenedesmus subspicatus (Algae; inhibition of growth rate) 1088 mg/L/72 hr; closed system with aeration

EC50 Daphnia magna (Water flea, 6-24 hr old; immobilization) 290 mg/L/24 hr; static

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 0.11 and 3.8(2), indicate that 2-nitropropane is expected to have very high mobility in soil(SRC). Volatilization of 2-nitropropane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.19X10-4 atm-cu m/mole(SRC) derived from a vapor pressure of 17.2 mm Hg(3) and a water solubility of 1.70X10+4 mg/L(4). 2-Nitropropane is expected to volatilize from dry soil surfaces(SRC) based upon the estimated vapor pressure(3). Half-lives of 2-nitropropane measured during aerobic batch laboratory microcosm experiments were 0.66 days in an acid clay soil (0.94% OC, pH 4.8) and 0.5 days in a basic sandy loam soil (3.25% OC, pH 7.8)(5,6). However, experiments were not corrected for potential loss due to volatilization(5,6). Biodegradation in soil is expected to be slow based on 3.0 and 1.2% conversion to CO2 in aerobic and anaerobic soil, respectively, after 35 days(7,8).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 0.11 and 3.8(2), indicate that 2-nitropropane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.19X10-4 atm-cu m/mole(SRC) derived from a vapor pressure of 17.2 mm Hg(4) and a water solubility of 1.70X10+4 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6 hours and 6 days, respectively(SRC). The pKa of 2-nitropropane is 7.68(6), indicating that this compound will partially exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(7). According to a classification scheme(8), BCF values of <8.4(9,10), suggest bioconcentration in aquatic organisms is low(SRC). Biodegradation in water is expected to be slow based on 0.8% mineralization after 5 days using activated sludge and 0.1-14% degradation in 28 day closed-bottle test(9-11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-nitropropane, which has an estimated vapor pressure of 17.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-nitropropane is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 95 days(SRC), calculated from its rate constant of 2.60X10-13 cu cm/molecule-sec at 25 °C(3). 2-Nitropropane is expected to undergo direct photolysis in the atmosphere based on 95% degradation after 24 hours and a half-life of 9.8 days measured during tests for photodegradation(4,5).

The substance can be absorbed into the body by inhalation of its vapour and by ingestion.

inhalation, ingestion, skin and/or eye contact

/AQUATIC SPECIES/ At 22 °C the 96-hr LC50 for fathead minnows (Pimephales promelas) was >210 mg/L. Aeration of the holding tanks during the toxicity test produced flawed results because 2-NP was lost continuously by volatilization and a nominal highest concentration of 612.5 mg/L was reduced to 496 mg/L at the start of the test and to 210 mg/L by 96 hr. There was no significant mortality at concentrations of 2-NP below 210 mg/L although at lower concentrations it did produce severe (though undescribed) sublethal effects.

/AQUATIC SPECIES/ The lowest concentration of 2-NP in sea water inducing narcosis in barnacle larvae at 18-22 °C was approximately 0.7-0.8 g/L.

/OTHER TERRESTRIAL SPECIES/ Observations on non-mammalian terrestrial organisms are limited to two related species, the oriental fruit fly (Dacus dorsalis) and the Mediterranean fruit fly (Ceratitis capitata). ... The 2-hr LC50 values for eggs and larvae of the oriental fruit fly were >103 and 75 g/cu m (>28,300 and 20,600 ppm), respectively, and for the Mediterranean fruit fly, >103 and 35 g/cu m (>28,300 and 9600 ppm), respectively. These observations, in summary, suggest a fairly low acute toxicity to non-mammalian organisms.

Cough. Dizziness. Drowsiness. Headache. Nausea. Vomiting. Diarrhoea. Weakness. Shortness of breath.

Dry skin. Redness.

Redness. Pain.

Further see Inhalation.

irritation eyes, skin, nose, respiratory system; headache, anorexia, nausea, vomiting, diarrhea; kidney, liver damage; [potential occupational carcinogen]

2-Nitropropane

Hepatic

2 x 10 ^-2 mg/m^3

All employees with a potential exposure to 2-nitropropane should be placed under a medical monitoring program which includes: history and medical examinations with specific emphasis on liver function tests.

Preplacement and periodic examination should consider respiratory and central nervous system effects as well as kidney function. Heinz bodies and methemoglobin levels are of interest.

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

F005; When 2-nitropropane is a spent solvent, it is classified as a hazardous waste from a nonspecific source (F005), as stated in 40 CFR 261.31, and must be managed according to State and/or Federal hazardous waste regulations.

U171; As stipulated in 40 CFR 261.33, when 2-nitropropane, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-Nitropropane is included on this list.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Nitropropane is produced, as an intermediate or a final product, by process units covered under this subpart.. /Nitropropane/

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 2-Nitropropane is included on this list.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

...To clarify the mechanism of carcinogenesis by 2-NP, we investigated DNA damage by 2-NP metabolites, N-isopropylhydroxylamine (IPHA) and hydroxylamine-O-sulfonic acid (HAS), using 32P-5'-end-labelled DNA fragments obtained from genes that are relevant to human cancer. In the presence of Fe(III) EDTA, both IPHA and HAS caused DNA damage at every nucleotide position without marked site preference. The damage was inhibited by free hydroxyl radical (-*OH) scavengers, catalase and deferoxamine mesilate, an iron chelating agent. These results suggest that the DNA damage was caused by -*OH generated via H(2)O(2) by both IPHA and HAS. In contrast, in the presence of Cu(II), IPHA frequently caused DNA damage at thymine. The Cu(II)-mediated DNA damage caused by IPHA was inhibited by catalase, methional and bathocuproine, a Cu(I)-specific chelator, suggesting the involvement of H(2)O(2) and Cu(I). These results suggest that the DNA damage induced by IPHA in the presence of Cu(II) was caused by a reactive oxygen species like the Cu(I)-hydroperoxo complex. On the other hand, HAS most frequently induced DNA damage at 5'-TG-3', 5'-GG-3' and 5'-GGG-3' sequences. Catalase and methional only partly inhibited the Cu(II)-mediated DNA damage caused by HAS, suggesting that the reactive oxygen species and another reactive species participate in this process. Formation of 8-oxodG by IPHA or HAS increased in the presence of metal ions. This study suggests that metal-mediated DNA damage caused by 2-NP metabolites plays an important role in the mutagenicity and the carcinogenicity of 2-NP.

Limited data... yielded a half-life for rats of approximately 80 min for 2-NP in plasma following a 3-hr exposure to a concentration of 728 mg/cu m (200 ppm). ...However, /a seperate study/ found that disappearance of the 14C label of the2-NP from the plasma was markedly slower and biphasic. During the first 12 hr following exposure to 560.6 mg/cu m (154 ppm), the half-life for plasma radioactivity was 172 min and, following exposure to 73 mg/cu m (20 ppm), 354 min. After 12 hr, loss of radioactivity from plasma was much slower, the half-life being approximtely 35-36 hr for both doses /(73 mg/cu m (20 ppm) and to 560.6 mg/cu m (154 ppm))/.

...The plasma half-life of intravenous doses of 0.01-0.05 g/kg in rats was 45 min during the first 4 hr. Loss was linear over this dose range and could be described by an open single-compartment model. They suggested that the measured loss from plasma may be due in part to spontaneous conversion of 2-NP to its anionic form, 2-NP nitronate.

2-Nitropropane has been shown to be metabolized to nitrous acid and acetone in rats.

Liver microsomes from phenobarbital pretreated rats can convert 2-nitropropane to acetone and nitrate in the presence of NADPH and oxygen.

14C-labeled 2-nitropropane was administered to chimpanzees and rats, the 14C-labeled biotransformation metabolites were principally carbon dioxide, acetone and isopropanol. ... It has been postulated that N-nitro compounds and oxygen radicals are reactive intermediates in the denitrification of 2-nitropropane.

The enzymatic system oxidizing 2-nitropropane (2-NP) to acetone and nitrite was identified through in vitro experiments using microsomes isolated from mammalian liver. /It was/ determined that cytochrome P-450, in liver microsomes from phenobarbital-pretreated rats, bound 2-NP. /It was/ subsequently reported that liver microsomes from rats pretreated with phenobarbital or 3-methylcholanthrene rapidly catalysed the oxidation of 2-NP to acetone and nitrite. The latter were produced in roughly equal quantities. Surprisingly, however, the rate of this reaction was not diminished under conditions of reduced oxygen pressure. The activity of preparations from untreated control rats was generally very low. /It was/ demonstrated that this enzyme system in rats was active in metabolizing other aliphatic nitro compounds. ...Working with mice, /researchers/ obtained somewhat different results. They reported rapid denitrification of 2-NP to nitrite and acetone by liver microsomes from untreated mice,and an acetone production at least twice the nitrite release. These authors suggested that multiple forms of cytochrome P-450 are involved, and claimed that nitrite is sequestered in the reaction mixture and that denitrification of 2-NP may involve a reductive or at least non-oxidative pathway as well as an oxidative pathway. They also noted large differences in the rates of hepatic microsomal enzymatic nitrite release among the five strains of mice tested. ...Hepatic microsomes from uninduced rabbits could denitrify a compound related to 2-NP, 2-nitro-1-phenylpropane. In addition to oxidative denitrification, a reductive pathway has been shown to occur in cultured hepatocytes from Wistar rats and in V79 Chinese hamster cells. Nitroreduction was indicated by the fact that the cells formed acetone oxime, the tautomeric form of nitrosopropane.

For more Metabolism/Metabolites (Complete) data for 2-NITROPROPANE (8 total), please visit the HSDB record page.

Following absorption by the gastro-intestinal tract and the lungs, part is eliminated unchanged in the expired air, part excreted in the urine as nitrite and nitrate. There is no evidence of absorption by the skin sufficient to cause systemic injury.

The pharmacokinetics of [14C]-2-nitropropane (2-NP) were studied in male rats exposed for 6 hr to 20 or 154 ppm. At least 40% of the inhaled compound was absorbed. Blood concentrations of 2-NP measured by gas chromatographic analysis decreased in an apparent first order manner (half life = 48 min). Half lives for the biphasic elimination of radioactivity from blood were two to four times longer, indicating that metabolites have a greater potential to accumulate. The major route of excretion was the expired air. About half of the administered radioactivity was recovered as 14CO2. Numerous differences in kinetic parameters observed at the two exposure concentrations indicated nonlinear kinetics at 154 ppm and higher.There were no differences in uptake or exhalation processes between males and females, but metabolic processes differed. A first-order, low-affinity but high capacity metabolic pathway was more than twice as active in females. The saturable pathway was predominant in females at exposure concentrations up to 180 ppm but only up to 60 ppm in males. Because males are more sensitive to hepatoxicity, genotoxicity, and carcinogenicity produced by inhalation of 2-NP, /it was/ concluded that these effects are produced by the metabolite resulting from the first-order pathway.

...Immediately following exposure to 728 mg/cu m (200 ppm) for 3 hr, plasma contained approximately 0.4% as 2-nitropropane (2-NP) and 7.2% as metabolitesof the 2-NP inhaled. The metabolites were mainly acetone but also included a small amount of isopropanol. These percentages were estimated from the results ... and normative data for the laboratory rat, and support rapid pulmonary uptake of 2-NP since 2-NP and its metabolites sequestered elsewhere in the body and loss of metabolized 2-NP during exposure were not considered.

The rate of 2-nitropropane (2-NP) uptake by rats from intraperitoneal injection was examined. Ten minutes after an injection of 25 mg/kg, the blood plasma contained 3.3% of the dose as 2-NP and 1.9% as metabolites, acetone, and isopropanol, indicating an uptake of >5.2% since presumably some of the dose was already lost from the body and to other tissues in the body during this initial period. These percentages were estimated from the data ... and normative data for the laboratory rat. A dose of 50 mg/kg yielded partially dissimilar results. The 10-min average value was low and also had a very large standard deviation. This may have reflected large differences among the rats in their initial uptake rates for 2-NP or an experimental problem such as injection into the gastrointestinal tract rather than the peritoneal cavity. Blood plasma contained, 10 min after injection, only 1.4% of the dose as 2-NP and 1.3% as acetone and isopropanol. These data indicate that uptake from the peritoneal cavity is fairly rapid, and suggest that the relatively slower uptake of the 50-mg/kg dose may have reflected saturation of the uptake mechanisms, since initial concentrations in the plasma did not exceed those following the 25-mg/kg dose.

For more Absorption, Distribution and Excretion (Complete) data for 2-NITROPROPANE (12 total), please visit the HSDB record page.

2-Nitropropane is primarily used as a solvent for organic compounds, coatings, inks, dyes, adhesives, and vinyl resins. It improves drying time, insures more complete solvent release, provides better flow characteristics, and insures greater pigment dispersion. 2-Nitropropane 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.

Used as additive to solvents in concentrations from 5% to 25% to improve drying or flowing characteristics; these solvents are used for coatings, chlorinated rubbers, inks, and adhesives; [ACGIH] Occupational exposure to 2-NP may occur in many industries including industrial construction and maintenance, printing (rotogravure and flexographic inks), highway maintenance (traffic markings), shipbuilding and maintenance (marine coatings), furniture, and plastic products. [http:www.cdc.gov/niosh/80-142.html]

Painting (Solvents) [Category: Paint]

Lithography printing [Category: Hobbies]

For 2-nitropropane (USEPA/OPP Pesticide Code: 600029) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Solvent in inks, paints, adhesives, varnishes, polymers, synthetic material; as chemical intermediate.

2023: 47,860,367 lb

Propane, 2-nitro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1977) 1.36X10+10 G (ESTIMATE)

(1982) PROBABLY GREATER THAN 2.27X10+6 G

(1986) >10 million - 50 million pounds

For more U.S. Production (Complete) data for 2-NITROPROPANE (8 total), please visit the HSDB record page.

... Produced by high-temperature vapor-phase nitration of propane. This process which employs nitric acid as the nitrating agent, is based on free radical reaction, in which the active species is the NO2 radical. ... Individual nitroalkanes are then obtained as pure products by fractional column distillation.

Preparation: ... Hass et al, US 1967667 (1934 to Purdue Research Foundation)

Technical: 94+ % pure.

/2-NITROPROPANE/...HAS FOLLOWING TRADE NAMES: NIPAR S-20 (COMMERCIAL GRADE 2-NITROPROPANE) & NIPAR S-30 (MIXT OF 1- & 2-NITROPROPANE).

All Other Basic Organic Chemical Manufacturing

Propane, 2-nitro-: ACTIVE