3-Methylpyridin

log Kow = 1.20

1.20

0.957 (USCG, 1999) - Less dense than water; will float

0.9566 at 20 °C/4 °C

Relative density (water = 1): 0.96

0.9613 @ 20°C

Very soluble (NTP, 1992)

Miscible with water at 20 °C

Miscible with alcohol, ether

Very soluble in acetone; soluble in carbon tetrachloride

Solubility in water: miscible

97 °F (NTP, 1992)

38 °C

37 °C (99 °F) (Closed cup)

38 °C c.c.

290 to 291 °F at 760 mmHg (NTP, 1992)

144.1 °C

143-144 °C

144.1 °C @760 [mm Hg]

This chemical does not meet GHS hazard criteria for 2% (36 of 1774) of reports.

Danger

H226 (95.7%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P337+P317, P361+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1774 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Chemical: Pyridine, 3-methyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com.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

Pyridine, 3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyridine, 3-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: 11-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/2119

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

Special Hazards of Combustion Products: Vapors may travel considerable distance to a source of ignition and flashback. Forms explosive mixtures in air. Emits toxic fumes under fire conditions. (USCG, 1999)

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 38 °C explosive vapour/air mixtures may be formed.

Moderate fire risk.

Flammable when exposed to heat or flame.

HARMFUL if swallowed, inhaled or absorbed through skin. Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes and skin. Inhalation may be fatal as a result of spasm, inflammation of larynx and bronchi, chemical pneumonitis and pulmonary edema. Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea and vomiting. (USCG, 1999)

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] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; May be absorbed through skin; Causes CNS depression in high-dose animal studies; [MSDSonline] An irritant that can cause CNS depression; In one case, a worker exposed for 11 years had elevated liver enzymes; Liver changes occur in rats exposed to chronic high doses; [AIHA]

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

BETA-PICOLINE may react with oxidizing materials (NTP, 1992). Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

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. 3-Methylpyridine is produced, as an intermediate or a final product, by process units covered under this subpart.

Fires involving this material should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

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.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

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 flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical, or carbon dioxide. /Picolines/

Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Hygroscopic. Storage class (TRGS 510): Flammable liquids.

Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to form explosive concentrations. Vapours can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated 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.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Waste treatment methods. Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

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 in industry is conflicting. The benefit 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.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic charge.

Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

For more Preventive Measures (Complete) data for 3-METHYLPYRIDINE (6 total), please visit the HSDB record page.

The three IQ (2-amino-3-methylimidazo(4,5-f) quinoline) compounds IQ, MeIQx (2-amino-3,4-dimethyl (4,5-f) quinoxaline) and MeIQ (2-amino-3,4-dimethylimidazo(4,5-f)quinoline) have been found in boiled pork juice. To determine which Maillard reaction products are important in the formation of IQ-type mutagens in boiled pork juice, six Maillard reaction products were separately added to the porkjuice before reflux boiling and then the mutagenicity of each sample was examined with Salmonella typhimurium TA98 in the presence of S9 mix. The addition of four Maillard reaction products enhanced the mutagenicity of pork juice 1.2-2.9-fold after reflux boiling. The highest level of enhancement was observed with tetrahydrothiophene, followed by 2,3-dimethylpyrazine, 3-methylpyridine and 2-methylpyridine. However, the addition of 2-acetylpyrrole and imidazole greatly inhibited the mutagenicity of pork juice.

3-Methylpyridine partially relieved the ataxia induced by tri-o-cresyl phosphate in hens.

LD50; Species: Wild bird oral 1 g/kg

LC50; Species: Pimephales promelas (Fathead Minnow) age 29 days, length 18.1 mm, weight 0.077 g; Conditions: freshwater, flow through, 24.1 °C, pH 7.8, hardness 43.5 mg/L CaCO3, alkalinity 44.0 mg/L CaCO3, dissolved oxygen 7.2 mg/L; Concentration: 144000 ug/L for 96 hr (95% confidence interval: 131000-160000 ug/L) /99% purity/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 115(SRC), determined from a structure estimation method(2), indicates that 3-methylpyridine is expected to have high mobility in soil(SRC). The pKa of 3-methylpyridine is 5.63(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). Soil studies with 2-methylpyridine(5), a compound expected to have similar sorption properties as 3-methylpryidine(SRC), demonstrated that Koc can vary with pH with lowest adsorption occurring in the non-ionized form(5). Volatilization of 3-methylpyridine from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 7.73X10-6 atm-cu m/mole(6). 2-Methylpyridine is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.05 mm Hg at 25 °C(7). 3-Methylpyridine is expected to biodegrade fairly rapidly in aerobic soil; however, under anaerobic conditions, this compound may be persistent(8,9). 3-Methylpyridine was added to aerobic Fincastle silt loam for a period of 32 days; 69.3% of the available nitrogen was released after this time(8). However, in an aerobic surface soil experiment, only 35% biodegradation was reported in 3 months while in anaerobic surface soil, under denitrifying and sulfidogenic conditions, 50 and 10 to 20% of the initially added 3-methylpyridine was biodegraded, respectively, in 3 months(9).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 115(SRC), determined from a structure estimation method(2), indicates that 3-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 7.73X10-6 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 5 and 37 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 1.20(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Low bioconcentration was reported for BCF tests using carp (Cyprinus carpio)(7). Rapid biodegradation under aerobic conditions is likely although 3-methylpyridine seems resistant to biodegradation under anaerobic conditions(8,9). 3-Methylpyridine was rapidly biodegraded in acclimated aerobic natural waters with complete removal within 2 to 4 days(8). However, in sulfidogenic estuarine sediments, 3-methylpyridine was not biodegraded over 200 days(9). 3-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 3-methylpyridine in aqueous solution shows no absorption >290 nm(10); therefore, 3-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 6.05 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-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 7 days(SRC), calculated from its rate constant of 2.30X10-12 cu cm/molecule-sec at 25 °C(3). The UV absorption spectrum of 3-methylpyridine in aqueous solution shows no absorption >290 nm(4); therefore, 3-methylpyridine is not expected to be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION AND USE: 3-Methylpyridine is a colorless liquid. It is used as a solvent; intermediate in dye and resins industries; in manufacture of insecticides, waterproofing agents, niacin and niacinamide. HUMAN EXPOSURE AND TOXICITY: 3-Methylpyridine caused eye irritation, gastro-intestinal disturbances and central nervous system (CNS) effects in one worker and may have produced liver abnormalities and facial skin eruptions in another. ANIMAL STUDIES: 3-Methylpyridine was a marked skin irritant in rabbits and guinea-pigs and has caused severe eye irritation in rabbits.. It has affected electrophysiological parameters in rats. Moderate acute oral, dermal and inhalation toxicity was demonstrated in laboratory animals, the principal site of toxic attack being the CNS. Repeated inhalation exposure resulted in increased liver weight in rats. 3-Methylpyridine was tested in three independent bacterial gene mutation studies; all studies gave negative results in S. typhimurium or E. coli tester strains, with and without exogenous metabolic activation. In vivo, no significant increases in the frequencies of micronucleated erythrocytes were observed in peripheral blood of male or female mice. In NTP cancerogenicity studies there was equivocal evidence of carcinogenic activity of 3-methylpyridine in male mice based on increased incidences of alveolar/ bronchiolar adenoma and alveolar/bronchiolar adenoma or carcinoma (combined). There was clear evidence of carcinogenic activity of 3-methylpyridine in female mice based on the increased incidences of alveolar/ bronchiolar adenoma or carcinoma (combined) in the lung and of hepatocellular carcinoma and hepatoblastoma in the liver. In the similar studies in rats there was no evidence of carcinogenic activity of 3-methylpyridine in male rats. There was some evidence of carcinogenic activity of 3-methylpyridine in female rats based on increased incidences of alveolar/bronchiolar adenoma and alveolar/bronchiolar adenoma or carcinoma (combined).

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

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

Redness. Pain. Severe deep burns.

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

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; See the data in Chemical Explorer/[USEPA; ICSS Dashboard Application; Available from, as of June 27, 2014: http://actor.epa.gov/dashboard/]

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of October 22, 2014: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=108-99-6]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 3-methylpyridine can be estimated to be 115(SRC). According to a classification scheme(2), this estimated Koc value suggests that 3-methylpyridine is expected to have high mobility in soil. The pKa of 3-methylpyridine is 5.63(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). Soil studies with 2-methylpyridine(5), a compound expected to have similar sorption properties as 3-methylpryidine(SRC), demonstrated that Koc can vary with pH with lowest adsorption occurring in the non-ionized form(5).

Subchronic inhalation toxicity was evaluated in groups of 10 male Crl:CD(SD)BR rats exposed to atmospheres containing 3-methylpyridine at an analytically measured (by gas chromatograph) level of 0 or 290q33 ppm for 6 h/d, 5 d/week for 2 weeks. The test atmosphere was generated by pumping liquid test material into a heated flask and diluting the resulting vapors with air introduced into the flask and chamber. There were no mortalities. Clinical observations included no compound-related signs of toxicity. Clinical chemistry and hematological studies revealed no treatment- related changes. Necropsy revealed elevated mean absolute and relative liver weights which was reversible after 13 days recovery. There were no other signs of toxicity.

3-Methylpyridine (CAS # 108-99-6, 98%) was evaluated for mutagenicity in Chinese hamster V79 lung cells exposed to concentrations of 0, 3.25, 3.5, and 3.75 uL/mL/plate in triplicate cultures, at 3 uL/mL/plate in solitary culture, and 4 uL/mL/plate in duplicate, without rat liver S9 metabolic activation (due to negative results in Ames microsome test), each for 4 hours. Exposure levels were chosen to span cloning efficiencies ranging from 3.6 to 74.6% L/mL/plate in preliminary cytotoxicity assay, and treated cells were subcultured in nonselective and selective medium, respectively, to determine survival and mutagenicity. By study protocol, a reproducible dose-related response with a 10-fold increase in the mutation rate of controls at 1 or more doses constituted a biologically significant indication of mutagenicity. With correction for cell survival, no treatment-related increased mutation frequency was observed.

3-Methylpyridine (CAS # 108-99-6, 98%) was evaluated for DNA single-strand breaks in Chinese hamster V79 lung cells exposed to concentrations of 0, 2, 3, 4, and 5 uL/mL/plate for 4 hours without metabolic activation (due to a negative results in Ames microsome assay). Concentrations were chosen to span cloning efficiences from 0 to 90.4% in preliminary cytotoxicity testing, and a survival index (cloning efficiency) was determined by Coulter count of trypsinized control and treated cells following genotoxicity assay. By study protocol, a 3-fold increase in elution rate relative to concurrent control in 2 consecutive doses constituted a biologically significant indication of genotoxicity. With correction for cell survival, alkaline filter elution of lysed treated and control cells with fluorimetric quantification of the residual DNA/dye complex disclosed no significant increase in DNA single-strand breaks relative to controls.

3-Methylpyridine (CAS # 108-99-6) was evaluated for mutagenicity in cultured TA1535, TA1537, TA98, and TA100 strains of Salmonella typhimurium, both in the presence and absence of rat liver S-9 metabolic activation. In two independent assays, bacterial cultures in triplicate with and without metabolic activation were exposed to 0 (unspecified solvent control), 0.51, 1.63, 5.10, 16.30, and 51.0 uM/plate for 36-72 hours. Relative to vehicle and historical controls, exposures did not increase mean frequency of base-pair or frame-shift histidine revertants in any strain regardless of metabolic activation.

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

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. 3-Methylpyridine is produced, as an intermediate or a final product, by process units covered under this subpart.

Intraperitoneal admin to guinea pigs, rabbits, mice, & ferrets resulted in urinary excretioN of the N-oxide (approx 10% in rats, 40% in mice & guinea pigs).

Urinary excretioN of pyridine n-oxide was incr iN mice pretreated with phenobarbitone, compared to controls. 3-Methylcholanthrene had no appreciable effect.

N-Oxidation is a minor route for 3-methylpyridine biotransformation with 6.6, 4.2, & 0.7% biotransformation of the dose, respectively, being excreted in the urine of mice, rats & guinea pigs receiving ip doses of the chemical.

The % uptake of 3-methylpyridine by rats increased with dosage; elimination occurred in 2 phases, the duration of which also was dose dependent. Addition of a methyl group to pyridine greatly increased the rate of uptake into liver, kidney & brain or rats.

Used as a solvent (pharmaceuticals, resins, and dyestuffs), rubber accelerator, laboratory reagent, and chemical intermediate; [HSDB] Picolines are constituents in cigarette smoke, bone oil, coal tar, and coke oven emissions. [AIHA] Used as a flavoring agent in foods and beverages; [IARC Monographs - 122]

Solvent; intermediate in dye and resins industries; in the manufacture of insecticides, waterproofing agents, niacin and niacinamide.

Solvent in synthesis of pharmaceuticals, resins, dyestuffs, rubber accelerators, insecticides. preparation of nicotinic acid and nicotinic acid amide, waterproofing agents, laboratory reagent.

Used as a chemical intermediate for the synthesis of: 3-chloro-2-hydroxy-5-trifluoromethylpyridine; 2-hydroxy-5-(trifluoromethyl)pyridine; nicotinonitrile

The predominant use of 3-methylpyridine is as a starting material for agrochemicals and pharmaceuticals. For example, it is used to make insecticides such as chlorpyrifos, food additives, eg, niacin and its amide, and herbicides, eg, fluazifop-butyl.

3-Methylpyridine may serve as an important source of nicotinic acid for dietary supplements.

2023: 7,000,000 - <8,500,000 lb

(1989) ca. 9000 metric ton/year

3-Methylpyridine 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).

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Pyridine, 3-methyl-. Aggregated National Production Volume: 10 to < 50 million pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Pyridine, 3-methyl-. National Production Volume: Withheld.

In a vapor-phase reaction over a nickel- containing catalyst in the presence of hydrogen, 2-methylglutaronitrile gives 3-methylpiperidine, which then undergoes dehydrogenation over palladium - alumina to give 3-methylpyridine.

From cyclohexylamine plus ammonia and zinc chloride, also from coal tar and bone oil.

Acetaldehyde + formaldehyde + ammonia (Reilly synthesis; coproduced with pyridine/alpha-picoline/gamma-picoline)

Acrolein + ammonia (Daicel process; coproduced with pyridine)

All Other Basic Organic Chemical Manufacturing

Pyridine, 3-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/