5-Ethyl-2-methylpyridine

Nitrogen Compounds -> Pyridines

Corrosives

Sharp, penetrating odor

Strong aromatic odor

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

Specific gravity: 0.9184 @ 23 °C/4 °C

Density (at 20 °C): 0.92 g/cm³

Relative density of the vapour/air-mixture at °C (air = 1): 1.01

0.917-0.923

Sol in alc, ether, benzene, dilute acids, concn sulfuric acid

Very soluble in acetone

In water, 1.2 g/100 ml @ 29 °C

12 mg/mL at 20 °C

Solubility in water, g/l at 20 °C: 12 (moderate)

Slightly soluble in water and fat

155 °F (USCG, 1999)

68 °C

155 °F, 68 °C (OPEN CUP)

68 °C o.c.

352 °F at 760 mmHg (USCG, 1999)

177.8 °C @ 747 mm Hg

172.00 to 175.00 °C. @ 760.00 mm Hg

178.3 °C

172-175 °C

Danger

H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1711 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H227: Combustible liquid [Warning Flammable liquids]

Chemical: Pyridine, 5-ethyl-2-methyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com.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

Pyridine, 5-ethyl-2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyridine, 5-ethyl-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: 18-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/10174

5-Ethyl-2-picoline: 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: Irritating vapors are generated when heated (USCG, 1999)

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 68 °C explosive vapour/air mixtures may be formed. Gas/air mixtures are explosive.

Breathing of vapors will cause vomiting and chest discomfort. Contact with liquid causes skin and eye burns. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Emergency treatment: Pyridine; Pyridine is an irritant that causes CNS depression after ingestion of 1/2 cup or inhalation of 6-12 ppm; It can cause liver and kidney injury; [HSDB] A severe irritant on rabbit skin; [RTECS] May cause burns to skin and eyes; [CAMEO] Corrosive to skin and eyes, based on animal studies; [CHEMINFO] Safe when used as a flavoring agent in food; [JECFA] Causes burns; Harmful by inhalation or ingestion; [Aldrich MSDS] See Pyridine.

2-METHYL-5-ETHYLPYRIDINE 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. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. A mixture of nitric acid and methyl ethyl pyridine was placed in an autoclave and heated and stirred for 40 minutes. The emergency vent opened due to a sudden pressure rise, then an explosion occurred after about 90 seconds [Chem. Eng. News 30:3348. 1952].

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use dry powder, foam, carbon dioxide, water spray. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air. Refer for medical attention.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. Refer immediately for medical attention.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

INHALATION: remove victim to fresh air; give oxygen if breathing is difficult; call a physician.

General First Aid:

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in covered 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.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

LC50 Pimephales promelas (fathead minnow) 81.1 mg/l/96 hr (confidence limit 77.6 - 84.8 mg/l), flow-through bioassay with measured concentrations, 26.2 °C, dissolved oxygen 5.9 mg/l, hardness 45.5 mg/l CaCO3, alkalinity 42.0 mg/l CaCO3, and pH 7.49.

EC50 Pimephales promelas (fathead minnow) 69.8 mg/l/96 hr (confidence limit 61.2 - 79.6 mg/l), flow-through bioassay with measured concentrations, 26.2 °C, dissolved oxygen 5.9 mg/l, hardness 45.5 mg/l CaCO3, alkalinity 42.0 mg/l CaCO3, and pH 7.49. Effect: loss of equilibrium.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a structure estimation method(2), indicates that 2-methyl-5-ethylpyridine is expected to have moderate mobility in soil(SRC). 2-Methyl-5-ethylpyridine has a pKa of 6.51(5), which indicates that this compound will exist mainly in the protonated form in moist acidic and neutral soils, and cations adsorb more strongly to soils than neutral molecules. Therefore, the mobility of 2-methyl-5-ethylpyridine is expected to be much lower in acidic and neutral soils than in alkaline soils(SRC). Volatilization of the neutral species of 2-methyl-5-ethylpyridine from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 1.43 mm Hg(3), and water solubility, 12,000 mg/l(6). However, the protonated form will not volatilize(SRC). The potential for volatilization of 2-methyl-5-ethylpyridine from dry soil surfaces may exist(SRC) based upon its vapor pressure(3). Based on an aerobic column study using aquifer sediment, 2-methyl-5-ethylpyridine is expected to biodegrade slowly in soil. After 35 days of operation, only 43.4% of the initially applied 2-methyl-5-ethylpyridine was removed(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a structure estimation method(2), indicates that 2-methyl-5-ethylpyridine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.9X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 1.43 mm Hg(4), and water solubility, 12,000 mg/l(9). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 20 days, respectively(SRC). However, the pKa of 2-methyl-5-ethylpyridine is 6.51(8), indicating this compound will exist in the ionized form in acidic and neutral waters and cations do not volatilize(SRC). According to a classification scheme(5), an estimated BCF of 14(SRC), from an estimated log Kow of 2.4(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Based on an aerobic column study using aquifer sediment, 2-methyl-5-ethylpyridine is expected to biodegrade slowly in water. After 35 days of operation, only 43.4% of the initially applied 2-methyl-5-ethylpyridine was removed(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-methyl-5-ethylpyridine, which has a vapor pressure of 1.43 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase 2-methyl-5-ethylpyridine 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 2.4X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

2-Methyl-5-ethylpyridine was qualitatively identified as a volatile component of fried chicken(1) and mutton(3). 2-Methyl-5-ethylpyridine was tentatively identified in salt-fermented shrimp paste from Korea at a concentration of 140 ng/g(2). 5-Ethyl-2-methyl-pyridine was found in peppermint oils at unreported concentrations(4).

Cough. Sore throat.

Redness. Pain. Skin burns.

Redness. Pain.

Sore throat. Burning sensation behind the breastbone. Abdominal pain.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-methyl-5-ethylpyridine can be estimated to be 170(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-methyl-5-ethylpyridine is expected to have moderate mobility in soil. The pKa of 2-methyl-5-ethylpyridine is 6.51(3), which indicates that this compound will exist in the protonated form under acidic and neutral conditions. Cations adsorb more strongly to soil surfaces than neutral molecules thus adsorption of 2-methyl-5-ethylpyridine may be greater in acidic and neutral soils(SRC).

2-Methyl-5-ethyl pyridine (CAS # 104-90-5) was evaluated for subacute oral toxicity in Harlan-Wistar albino rats (5/sex/dose group) fed nominal doses of 0 (negative control Group A), 0 (negative control Group B), 0.16, 0.40, and 1.0 g/kg/day by dietary inclusion for 7 days. Based on daily consumption, the attained dosages did not deviate significantly from targets. All treated and control animals survived to terminal necropsy and no overt toxicity was reported in 7-day study. Clinical signs of toxicity included dramatically and statistically significant (p < 0.001) depression of bodyweight gains on Days 1, 4, and 7 in both high dose males and females. Relative to control Group B, growth rates were also significantly (p < 0.05) reduced on Day 7 in 0.40 g/kg/day females. Relative liver weights (as percentage of bodyweight) in 1.0 g/kg/day females were significantly (p < 0.01) elevated relative to those of control Group 2 after 7 days, but not as compared to control Group 1. Microscopic examination of high dose animals failed to identify treatment-related lesions in excess of historical and study controls. Based on bodyweight, liver and kidney weights, and histopathology, the authors reported a maximum no significant ill-effect level (MiE) as 0.40 g/kg/day and calculated a ratio of LD50 (0.566 g/kg) and MiE as 1.44, probably indicating a low degree of chronicity.

4-Methylpyridine (CAS # 108- 89-4) was evaluated for mutagenicity in Chinese hamster V79 lung cells exposed to concentrations of 0, 3.75, 4, 4.25, and 4.5 uL/mL/plate in triplicate cultures for 4 hours without rat liver S9 metabolic activation (due to negative results in Ames microsome test). Exposure levels were chosen to span cloning efficiencies ranging from 1.3 to 82.8% 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 significant treatment-related increased mutation frequency was observed.

4-Methylpyridine (CAS # 108-89-4) was evaluated for DNA single-strand breaks in Chinese hamster V79 lung cells exposed to concentrations of 0, 1, 2, 3, 3.5, 4, and 4.5 uL/mL/plate for 4 hours without metabolic activation (due to negative result in Ames microsome test). Concentrations were chosen to span cloning efficiences from 1.5 to 98.9% 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.

4-Methylpyridine (CAS # 108-89-4) 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.

2-Methyl-5-ethylpyridine's production and use in the manufacture of nicotinic acid and nicotinamide, and vinyl pyridines for copolymers, as an intermediate for germicides and textile finishes and as a corrosion inhibitor for chlorinated solvents(1) may result in its release to the environment through various waste streams(SRC). 2-Methyl-5-ethylpyridine is also released to the environment via effluents from oil processing facilities(2,3).

PYRIDINE & ITS ALKYL DERIVATIVES ARE ABSORBED FROM GI TRACT, INTRAPERITONEAL CAVITY & LUNGS. PERITONEAL ABSORPTION IS APPARENTLY ONLY SLIGHTLY MORE RAPID & COMPLETE THAN GI ABSORPTION ... IN GENERAL THE BASES ARE RAPIDLY ABSORBED THROUGH INTACT SKIN. /ALKYL DERIVATIVES OF PYRIDINE/

MAJORITY OF /PYRIDINE/ DERIVATIVES TESTED ... PENETRATE INTACT GUINEA PIG SKIN READILY. AMINOPYRIDINES, VINYLPYRIDINES & 4-PICOLINE PENETRATE SKIN MOST RAPIDLY & AMYL DERIV & 5-ETHYL-2-METHYLPYRIDINE ARE LEAST READILY ABSORBED. /VINYLPYRIDINES/

Used as a corrosion inhibitor for chlorinated solvents and in the manufacturing of other chemicals (nicotinic acid, nicotinamide, vinyl pyridines for copolymers, germicides, insecticides, and textile finishes); [HSDB] Used as a solvent in organic synthesis; [eChemPortal: SIDSUNEP]

Metal Extraction and Refining [Category: Industry]

Mfr nicotinic acid and nicotinamide; vinyl pyridines for copolymers; int for germicides and textile finishes; corrosion inhibitor for chlorinated solvents

Intermediate for insecticides

... by heating acetaldehyde ammonia in a double vol of abs alc

2-Methyl-5-ethylpyridine is made by a liquid-phase process in a 70% yield from acetaldehyde or ethylene (80% yield).

Reaction of paraldehyde with aqueous ammonia in the liquid phase is carried out at 200-300 °C and 12-13 MPa in the presence of an ammonium salt...to give 2-methyl-5-ethylpyridine in about 70% yield.

2-Methyl-5-ethylpyridine is obtained in the presence of fluoride ions by the reaction of aqueous ammonia with acetaldehyde (or with paraldehyde, which slowly releases the monomer).

Grade: Technical

Grades or Purity: 99.9%

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Fabricated Metal Product Manufacturing

Pyridine, 5-ethyl-2-methyl-: ACTIVE

Picolines and other substituted pyridines are byproducts.