2-Methylpyridine

Nitrogen Compounds -> Pyridines

Nitrogen Compounds -> Pyridines

Flammable agents - 2nd degree

Flammable agents - 3rd degree

log Kow = 1.11

1.1

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

0.9443 at 20 °C/4 °C

Relative density (water = 1): 0.95

0.950 @ 15°C

greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)

Miscible in water at 20 °C

Very sol in acetone

Miscible with alcohol, ether

Solubility in water: miscible

97 °F (NTP, 1992)

26 °C

102 °F (39 °C)(Open cup)

26 °C c.c.

262 to 264 °F at 760 mmHg (NTP, 1992)

129.4 °C

128-129 °C

129 °C @760 [mm Hg]

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P321, P330, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 2.7% (11 of 409) of reports.

Danger

H226 (97.3%): Flammable liquid and vapor [Warning Flammable liquids]

Chemical: Pyridine, 2-methyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Pyridine, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyridine, 2-methyl- 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: 17-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17685

2-Methylpyridine: Does not have an individual approval but may be used under an appropriate group standard

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: When heated to decompo- sition, emits toxic fumes of cyanide.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 26 °C explosive vapour/air mixtures may be formed.

Moderate fire risk

Flammable liquid when exposed to heat or flame.

May cause first degree burns after short exposure and second degree burns after longer contact; Liver and kidney injury after chronic exposure have been reported. [CHRIS] See Pyridine.

A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation of high concentrations can cause unconsciousness; The liquid defats the skin; [ICSC] An irritant; Harmful if swallowed, inhaled, or absorbed through skin; A strong respiratory tract irritant; May cause convulsions; Oral LD50 (rat) = 790 mg/kg; [MSDSonline] An irritant that can cause CNS depression; Liver changes occur in rats exposed to chronic high doses; [AIHA] See Pyridine.

U191; As stipulated in 40 CFR 261.33, when 2-methylpyridine, 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).

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-Methylpyridine is included on this list. Effective date: 09/10/84; Sunset date: 09/10/94.

Fire Extinguishing Agents Not to Be Used: 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.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

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

Rinse mouth. Do NOT induce vomiting. 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.

To fight fire, use carbon dioxide, dry chemical.

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

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U191, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

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. A potential 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 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.

Personal protection: chemical protection suit including self-contained breathing apparatus. 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.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to disperse vapors and dilute standing pools of liquid. /Picolines/

Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. Do not handle broken packages unless wearing appropriate personal protective equipment. ... Wash away any material which may have contacted the body with copious amounts of water or soap and water. ... If contact with material anticipated, wear appropriate chemical protective clothing. /Picolines/

LC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through bioassay with measured concentrations, 25.6 °C, dissolved oxygen 7.0 mg/L, hardness 46.0 mg/L CaCO3, alkalinity 309 mg/L CaCO3, and pH 7.88; Concentration: 897 mg/L for 96 hr (confidence limit not reliable)

EC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through bioassay with measured concentrations, 25.6 °C, dissolved oxygen 7.0 mg/L, hardness 46.0 mg/L CaCO3, alkalinity 309 mg/L CaCO3, and pH 7.88; Concentration: 772 mg/L for 96 hr (confidence limit: 704-846 mg/L); Effect: loss of equilibrium

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 4 to 215, determined from sorption studies using 5 Eurosoil reference soils(2), indicate that 2-methylpyridine is expected to have very high to moderate mobility in soil(SRC). The pKa of 2-methylpyridine is 5.96(3), indicating that this compound will exist partially in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). In the Eurosoil tests, lowest adsorption occurred when 2-methylpyridine was in non-ionized form(2). Volatilization of the neutral species of 2-methylpyridine from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 9.96X10-6 atm-cu m/mole(5). 2-Methylpyridine is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 11.2 mm Hg at 25 °C(6). Results of various biodegradation studies indicate that 2-methylpyridine generally biodegrades readily under aerobic conditions, but biodegradation occurs much slower under anaerobic ocnditions(7). In one aerobic soil study, 97.3% biodegradation of 2-methylpyridine occurred when incubated in a silt loam soil for 16 days(8). 2-Methylpyridine was completely biodegraded in 2 weeks in an aerobic surface soil while in anaerobic surface soil only 10% biodegradation was reported in 3 months(9).

AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 4 to 215, determined from sorption studies using 5 Eurosoil reference soils(2), indicate that 2-methylpyridine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 9.96X10-6 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 and 30 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 1.11(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Low bioconcentration was reported for BCF tests using carp (Cyprinus carpio)(8). Results of various biodegradation studies indicate that 2-methylpyridine generally biodegrades readily under aerobic conditions, but biodegradation occurs much slower under anaerobic ocnditions(9). 2-Methylpyridine was completely biodegraded in 4 days in aerobic groundwater(10). In sulfidogenic estuarine sediments, 2-methylpyridine was not biodegraded over a 100-day period(11). 2-Methylpyridine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). The UV absorption spectrum of 2-methylpyridine in aqueous solution shows no absorption >290 nm(12); therefore, 2-methylpyridine is not expected to be susceptible to direct photolysis by sunlight(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-methylpyridine, which has a vapor pressure of 11.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-methylpyridine 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 6 days(SRC), calculated from its rate constant of 2.79X10-12 cu cm/molecule-sec at 25 °C(3). The UV absorption spectrum of 2-methylpyridine in aqueous solution shows no absorption >290 nm(4); therefore, 2-methylpyridine is not expected to be susceptible to direct photolysis by sunlight(SRC).

2-Methylpyridine has been identified as a volatile flavor compound in fried bacon(1), boiled beef(2), fried chicken(3) and frankfurters(4). 2-Methylpyridine has also been detected in coffee aroma(5) and identified as an aroma compound in the earth almond(6). Concentrations of 2-methylpyridine in 3 commercial fermented soybean curds from Hong Kong were 25.8, 17.2, and 99.7 ug/kg(7).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Neurotoxin - Other CNS neurotoxin

IDENTIFICATION AND USE: 2-Methylpyridine is a colorless liquid with a strong unpleasant odor. It is used as organic intermediate for rubber and dye chemicals, solvent, laboratory reagent. 2-Methylpyridine is a chemical intermediate for the synthesis of: 2-amino-6-methylpyridine; betahistine; bis-acodyl; clopyralid; 2-methylpiperidine; perhexiline; picloram; picolinic acid; thioridazine; 2-vinylpyridine. HUMAN EXPOSURE AND TOXICITY: 2-Methylpyridine causes local irritation on contact with the skin, mucous membranes and cornea. Clinical signs of intoxication caused by the methylpyridines include weight loss, diarrhea, weakness, ataxia and unconsciousness as well as CNS depression, headache, giddiness and vomiting. Chronic exposure to methylpyridine results in anemia and ocular and facial paralysis in addition to the previously mentioned symptoms. It has been alleged that the workmen exposed to picoline vapors may develop diplopia as a result of disturbance of the eye muscles. ANIMAL STUDIES: Eye and skin irritant in rabbits. Chronic administration to rats decreased glycogen level and increased glucose and lactic acid levels in liver of rats throughout most of the study. In developmental study in rats structure and composition of the liver and the structure andgrowth pattern of the skin were disrupted in the offspring. 2-Methylpyridine affected electrophysiological parameters in rats. Ames test with and without metabolic activation in Salmonella typhimurium TA98, TA100, TA97, TA102, 10-5000 ug/plate was negative.

Cough. Dizziness. Drowsiness. Headache. Nausea. Sore throat. Unconsciousness. Weakness.

MAY BE ABSORBED! Dry skin. Redness. Burning sensation. Pain. Blisters. Further see Inhalation.

Redness. Pain. Blurred vision. Severe deep burns.

Abdominal pain. Burning sensation. Diarrhoea. Vomiting. Further see Inhalation.

2-Methylpyridine has been identified in effluents from the following industries: timber products, organic chemicals, pharmaceuticals, and public owned treatment works(3). 2-Methylpyridine is contained in shale oil wastewater (5 ppm) and would be released to the atmosphere if the wastewater were heated as it would be when used to cool hot, retorted oil shale(1,5). It was also found in the effluents from an advanced publically-owned water treatment facility in Pomona, CA(2). Wastewater from coal gasification contained an estimated 3.71 ppm of 2-methylpyridine(4). 2-Methylpyridine has been detected at a mean concentration of 5.0 mg/L from 10 samples of low temperature carbonization wastewater from waste ammonia liquor(6).

The sorption behavior of 2-methylpyridine was studied in soil column tests using 5 Eurosoil reference soils having organic carbon content ranging from 0.33-1.85% and pH ranging from 5.2-8.6(1); measured Kd values ranging from 0.08 to 6.52(1) correspond to calculated Koc values of 4, 38, 70, 100 and 215(SRC); the lowest Koc value of 4 corresponds to Eurosoil 2 which had the highest pH value(8.6). The pKa of 2-methylpyridine is 5.96(2), indicating that this compound will exist partially in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(3). In the Eurosoil column tests(1), lowest adsorption occurred when 2-methylpyridine was in non-ionized form(1). Sorption of 2-methylpyridine to soil is primarily controlled by cation exchange and surface complex formation(1,4). According to a classification scheme(5), the Koc values suggest that 2-methylpyridine is expected to have very high to moderate mobility in soil.

Spectral studies of 2-methylpyridine adsorbed to hydrated and dehydrated silica indicate that hydrogen bonding occurs with silica surface silanols via the nitrogen atom on the pyridine ring and that this interaction is stronger than that between this compound and water(1). 2-Methylpyridine emerged under 2 soil column void volumes; soil columns were packed with soil cores from Rock Springs, WY to the original 1016 mm depth and shale-oil process water was used as the mobile phase(2); the pH and clay content of the soil were not specified(2); this indicates that soil is an effective adsorbent when less than this void volume of retort water is applied (as in small spills)(2); rainfall leaching after a spill will also probably enhance solute migration(2). When 2-methylpyridine was incubated at 28 °C in a soil inoculum, 4.8% was sorbed by soil(3).

Acute toxicity was evaluated in groups of male Sprague-Dawley rats (4 groups of 10 animals each) ingesting a single dose of A-picoline via gavage at doses of 950, 790, 550 and 0 mg/kg. In the group given 950 mg/kg there was significantly increased mortality, (4 of 10 rats died), the remaining 6 rats showed decreased body weight gain, and 2 of the 6 also showed signs of encephalomalacia. Doses of 0 to 750 mg/kg had no significant toxic effects on test animals.

Subchronic toxicity was evaluated in groups of male and female Sprague- Dawley rats (10/sex/concn level) exposed to A-picoline via inhalation in glass exposure chambers at nominal concentrations of 0, 5, 35 or 100 ppm, 5 days/week for 6 months, beginning at age 8 weeks. In male rats given 5 and 100 ppm there was significantly increased relative heart and liver weights. A statistically significant decrease in the red blood cell count was observed in both male and female rats exposed to the higher concentration of A-picoline (but this effect was not reproducible). Other parameters of clinical chemistry, urinalysis, and organ weights and histopathology were not consistently affected by the treatment.

INDOOR: A mean concentration of 0.07 ug/cu m 2-methylpyridine was reported in samples of air taken from non-smoking homes in Columbus, OH over one week in February 1991 (n=24; range=0.00 to 0.67 ug/cu m); in smoking homes, a mean concentration of 0.45 ug/cu 2-methylpyridine was reported (n=25; range=0.00 to 1.55 ug/cu m)(1).

SOURCE DOMINATED: Indoor and outdoor air in and near the shale oil wastewater treatment facility of Occidental Oil Shale Inc at the Logan Wash site, CO contained 7 and 28 ug/cu m of 2-methylpyridine, respectively(1). Rural air in an undeveloped area of the oil shale region as well as urban air (Boulder, CO) contained no 2-methylpyridine(1). The average daily ambient concentration for 2-methylpyridine based on 3 data points is 0.613 ppbv(2).

/SIGNS AND SYMPTOMS/ 2-Methylpyridine causes local irritation on contact with the skin, mucous membranes & cornea. Clinical signs of intoxication caused by the methylpyridines include weight loss, diarrhea, weakness, ataxia and unconsciousness as well as /CNS depression/, headache, nausea, giddines and vomiting. Chronic exposure to methylpyridine results in anemia and ocular and facial paralysis in addition to the previously mentioned symptoms.

/CASE REPORTS/ ... It has been alleged that the workmen exposed to picoline vapors may develop diplopia as a result of disturbance of the eye muscles. /Picolines/

/OTHER TOXICITY INFORMATION/ Reilly Industries Belgium In-House data: Workplace typical concentrations: 0.01 - 1.85 ppm (personal sampling workers 8hrs values). Fenceline typical concentrations: 0.4 - 4 ppb (fenceline monitoring data).

U191; As stipulated in 40 CFR 261.33, when 2-methylpyridine, 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).

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-Methylpyridine is included on this list. Effective date: 09/10/84; Sunset date: 09/10/94.

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 5000 lb or 2270 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).

... In rabbits and dogs /2-methylpyridine/ is oxidized to alpha-picolinic acid which is excreted in the urine. alpha-Picolinuric acid is also excreted by frogs administered alpha-picoline, but only in amounts less than 1% of the dose. In hens it is excreted partly as alpha-pyridinornithuric acid.

/It was observed that/ 96% of a 100 mg/kg oral dose of 2-methylpyridine administered to rats was excreted in the urine as picolinuric acid.

There also is evidence that 2-methylpyridine forms an N-methylated derivative in dogs.

Alpha-picoline was rapidly absorbed by blood & penetrated into liver, heart, spleen, lungs, & muscles during 1St 10-20 min following oral admin of 0.5 g/kg to rats. It was excreted in urine during 1St 48 hr.

Addition of a methyl group onto the pyridine molecule increases the rate of absorption of the resultant picolines into the liver, kidney, & brain of rats. After ip injection of the picolines, pharmacokinetic parameters were greatly dependent upon the position of the methyl group. For example, the residence time for beta-picoline in liver, brain, & kidney was > that of alpha- or gamma-picoline. Elimination of all four pyridines was biphasic in nature, the first phase being more prolonged for pyridine & beta-picoline than for alpha- or gamma-picoline.

The substance is rapidly absorbed by the blood and penetrated into liver, heart, spleen, lungs, brain and muscles during the first 10 - 20 minutes after oral administration of 500 mg/kg to rats. It is excreted in urine mainly during the first 48 hrs after administration. Prevalent accumulation in the liver within 1 hr. Within 2 days however, the levels of the substance in the organs was decreased to traces.

Used as a solvent and chemical intermediate for dyes and resins; [HSDB]

Used as an intermediate (dyes, resins, agrochemicals, and pharmaceuticals), solvent, and laboratory reagent; [HSDB] Found naturally in coal tar; Used as a solvent and to make dyes and resins; [MSDSonline] Picolines are constituents in cigarette smoke, bone oil, coal tar, and coke oven emissions. [AIHA]

Intermediate in dye and resins industries; solvent.

Organic intermediate for ... rubber chemicals, solvent, ... laboratory reagent.

Used as a chemical intermediate for the synthesis of: 2-amino-6-methylpyridine; betahistine; bis-acodyl; clopyralid; 2-methylpiperidine; perhexiline; ... picolinic acid; /and/ thioridazine.

The primary use of 2-methylpyridine is as a precursor of 2-vinylpyridine. It is also used in a variety of agrochemicals and pharmaceuticals, e.g., nitrapyrin to prevent loss of ammonia from fertilizers; picloram, a herbicide; and amprolium, a coccidiostat.

2023: 1,000,000 - <8,500,000 lb

(1972) PROBABLY GREATER THAN 1.82X10+6 GRAMS

(1975) 1.73X10+8 GRAMS

1.89X10+5 kg (1976)

(1989) ca. 8000 t/a

For more U.S. Production (Complete) data for 2-METHYLPYRIDINE (7 total), please visit the HSDB record page.

... The reaction of acrylonitrile and acetone, catalyzed by a primary aliphatic amine such as isopropylamine and a weak acid such as benzoic acid, occurs in the liquid phase at 180 °C and 2.2 MPa to give 5-oxohexanenitrile, with 91% selectivity. The acrylonitrile conversion is 86%. Then cyclization and dehydration of the initial product are carried out in the gas phase in the presence of hydrogen over a palladium, nickel, or cobalt- containing catalyst at ca. 240 °C to give 2-methylpyridine in 84% yield.

... Acetonitrile and acetylene react in the presence of cobaltocene as catalyst to give 2-methylpyridine in 76% yield.

Synthesis (40-50% yield) from cyclohexylamine with excess ammonia and zinc chloride at 350 °C.

Prepared from ethylene-mercuric acetate adduct and ammonia water (70% yield).

For more Methods of Manufacturing (Complete) data for 2-METHYLPYRIDINE (8 total), please visit the HSDB record page.

All Other Basic Organic Chemical Manufacturing

Pyridine, 2-methyl-: ACTIVE

Pyridine, methyl-: ACTIVE

Pyridine bases are a constituent of tars. They were isolated from coal tar or coal gas before synthetic manufacturing processes became established. The amounts contained in coal tar and coal gas are small, and the pyridine bases isolated from them are a mixture of many components. Thus, with a few exceptions, isolation of pure pyridine bases was expensive. Today, almost all pyridine bases are produced by synthesis. /Pridine bases/