4-Methylpyridine
-
4-Methylpyridine
structure -
-
CAS No:
108-89-4
-
Formula:
C6H7N
-
Chemical Name:
4-Methylpyridine
-
Synonyms:
Pyridine,4-methyl-;4-Picoline;4-Methylpyridine;γ-Picoline;Ba 35846;p-Methylpyridine;p-Picoline;γ-Methylpyridine;NSC 18252;82005-09-2;92075-35-9
- Categories:
-
CAS No:
Description
Clear light yellow liquid Picolines are colorless liquids. Strong, unpleasant, pyridine-like odor.“Picoline” is often used as mixed isomers.ChEBI: A methylpyridine in which the methyl substituent is at position 4.Colorless moderately volatile liquid.
4-Methylpyridine is the organic compound with the formula CH3C5H4N. It is one of the three isomers of methylpyridine. This pungent liquid is a building block for the synthesis of other heterocyclic compounds. Its conjugate acid, the 4-methylpyridinium ion, has a pKa of 5.98, about 0.7 units above that of pyridine itself.
4-methyl pyridine is a colorless moderately volatile liquid. (NTP, 1992)|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.
4-methyl pyridine is a colorless moderately volatile liquid. (NTP, 1992)|4-methylpyridine is a methylpyridine in which the methyl substituent is at position 4.
4-Methylpyridine Basic Attributes
93.13
93.13
104586
203-626-4
TJD6V9SSO7
0803
18252
2313
DTXSID4021892
Colorless liquid
29333955
Characteristics
12.9
1.2
Clear light yellow Liquid
0.9548 g/cm3 @ Temp: 20 °C
3.66 °C
145 °C @ Press: 760 Torr
134 °F
n 20/D 1.504(lit.)
H2O: soluble ;alcohol: soluble (lit.)
Flammables area
4 mm Hg ( 20 °C)
3.2 (vs air)
Oral-Rat LD50: 1290 mg/kg; Intraperitoneal-Mouse LD50: 335 mg/kg
Combustible in case of fire, high temperature and strong oxidant; decomposes toxic nitrogen oxide gas upon heating
1.3-8.7%(V)
Obnoxious, sweetish odor
6.00e-06 atm-m3/mole|Henry's Law constant = 6.00X10-6 atm-cu m/mol @ 25 °C
Kb at 25 °C = 1.1X10-8|pKa = 5.98
Turns brown if not very pure|Hydroxyl radical reaction rate constant = 2.69X10-12 cu cm/molecule-sec at 25 °C
Highly flammable.
Amines, Phosphines, and Pyridines
Highly Flammable
4-METHYL PYRIDINE 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.
37.51 kJ/mol at 145.36 °C; 44.56 kJ/mol at 25 °C
Critical temperature: 645.8 K; critical pressure: 4.68 MPa
Safety Information
III
3
UN 1992 3/PG 3
1
10-20/22-24-36/37/38
26-36-45
UT5425000
T
Completely packed, lightly placed; storeroom ventilated, away from open flame, high temperature, and stored separately from oxidants and acids
Stable under recommended storage conditions.
P261-P280-P305 + P351 + P338-P312
H226-H302 + H332-H311-H315-H319-H335
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.
Incompatible materials: Oxidizing agents.
UN 2313
P261; P280; P305 + P351 + P338; P312
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 57 °C explosive vapour/air mixtures may be formed.
|Danger|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|H226 (99.79%): Flammable liquid and vapor [Warning Flammable liquids]|Aggregated GHS information provided by 521 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: If you should spill this chemical, 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 acetone followed by washing with a strong 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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. RECOMMENDED GLOVE MATERIALS: Permeation data indicate that polyvinyl chloride gloves may provide protection to contact with this compound. Polyvinyl chloride over latex gloves is recommended. However, if this chemical makes direct contact with your gloves remove them at once. (NTP, 1992)|Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. Flame retardant antistatic protective clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Personnel protection: ... Wear appropriate chemical protective gloves, boots, and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Picolines/
Moderate fire risk.
Explosive limits , vol% in air: 1.3-8.7
To fight fire, use alcohol foam.|Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.|Use water spray to cool unopened containers.|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/
Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx).
Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors 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.
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.|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 4-METHYLPYRIDINE (6 total), please visit the HSDB record page.
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Picolines/|/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Picolines/|/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Picolines/|/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Picolines/|For more DOT Emergency Guidelines (Complete) data for 4-METHYLPYRIDINE (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials. /Picolines/|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article. /Picolines/
A severe skin & eye irritant.
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.
Fireproof. Separated from strong oxidants. Well closed.
A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
The substance is corrosive to the eyes and skin. The vapour is irritating to the respiratory tract. Exposure at high levels could cause unconsciousness.
The substance defats the skin, which may cause dryness or cracking.
NO open flames, NO sparks and NO smoking. Above 57 °C use a closed system, ventilation and explosion-proof electrical equipment.
PREVENT GENERATION OF MISTS!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.
4-Methylpyridine was detected in 1 of 6 wastewater effluents from energy related processes(1). The process water at a coal gasification facility in Gillette, WY contained 4-methylpyridine in trace quantities(1). Wastewater from coal gasification at the Grand Fork's Energy Technology Center, ND was also reported to contain 4-methylpyridine(2). In addition, wastewater effluent from a shale oil facility in Queensland, Australia was shown to contain 4-methylpyridine(3). Oil shale condensate retort water contained 4-methylpyridine at 6.3 mg/L(4).
URBAN: 4-Methylpyridine was not detected in the air of downtown Boulder, CO in Nov 1982(1).|INDOOR: A mean concentration of 0.09 ug/cu m 4-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 0.69 ug/cu m); in smoking homes, a mean concentration of 0.16 ug/cu m 4-methylpyridine was reported (n=25; range=0.00 to 0.94 ug/cu m)(1).|RURAL: 4-Methylpyridine was not detected in the air from an undeveloped location in CO in Nov 1982(1).|SOURCE DOMINATED: In Nov 1982, 4-methylpyridine was detected in the air outside an oil shale wastewater facility of Occidental Oil Shale Inc. at Logan Wash, CO(1).
4-Methylpyridine is reported to occur in cigarette smoke(1). The mainstream smoke of a popular 85 mm USA cigarette without filter tip contained 24.2 ug gamma-picoline (4-methylpyridine)(2).
Toxicity
moderately toxic
IDENTIFICATION AND USE: 4-Methylpyridine is a colorless liquid with an obnoxious, sweetish odor. It is used as a solvent in synthesis of pharmaceuticals, resins, dyestuffs, rubber accelerators, and pesticides.It is also used in the production of antituberculosis agent, isoniazid; waterproofing agents fo fabrics; as a laboratory reagent, catalyst, and curing agent. HUMAN EXPOSURE AND TOXICITY: Symptoms include occasional diarrhea, weight loss, anemia, and ocular and facial paralysis. 4-Methylpyridine induced a dose-related increased frequency of sister chromatid exchange in human lymphocyte cultures from three individuals. Chromosomal aberrations induced by 4-methylpyridine included: chromatid breaks; centromeric, intermediate and terminal chromosome breaks; terminal and interstitial deletions; translocation; dicentric chromosomes; and isochromosomes. ANIMAL STUDIES: 4-Methylpyridine was severely irritating in rabbit skin tests. It is a potent inhibitor of red cell cholinesterase and an effective miotic inhibitor in mice and rabbits. Adrenal cortisol production also is inhibited by 4-methylpyridine treatment. In neurophysilogical tests in rats 3-methylpyridine and 2-methylpyridine affected electrophysiological parameters more than did 4-methylpyridine. 4-Methylpyridine was not mutagenic in Chinese hamster lung cells, and it was not mutagenic when tested with Salmonella typhimurium strains TA97, TA98, TA100 and TA102.
The relationship between the mutagenicity of cobalt (II) heteroaromatic base complex and the strength of their coordinate bonds was examined ... . The mutagenicity of cobalt(II) chloride was studied in Salmonella test strains (TA-1537), (TA-2637), (TA-97a), and (TA-100) in combination with 4-substituted pyridines. The mixtures were divided into three groups based on spectral evidence of lowest relative strength of coordinate bonding (first group), intermediate strength bonding (second group), and highest strength bonding (third group). The first group of pyridine compounds included pyridine ... 4-methylpyridine, 4-ethylpyridine, 4-chloropyridine, and 4-bromopyridine. With these compounds cobalt (II) chloride demonstrated weak to marginal mutagenicity in (TA-1537), and/or (TA-2637), but not in (TA-98) or (TA-100). ... The second group of compounds included 4-aminopyridine and 4-dimethylaminopyridine. Equimolar mixtures of cobalt (II) chloride with these compounds was not mutagenic. The third group included 4-cyanopyridine ... . Equimolar mixtures of cobalt (II) chloride and ... /this/ compound /was/ not mutagenic. The only mixtures of cobalt (II) chloride and pyridines which demonstrated muagenicity in strains (TA-1537) and/or (TA-2637) were those which showed spectral evidence of only a moderate interaction between the metal cation and the pyridine derivatives. The maximum mutagenicity was noted when the mixture was equimolar.
LC50 Rat inhalation <17.5 mg/kg 2.5 hr|LD50 Rabbit dermal 270 mg/kg|LD50 Rat oral 1.29 g/kg|LD50 Long-Evans hooded rat ip 162 mg/kg|For more Non-Human Toxicity Values (Complete) data for 4-METHYLPYRIDINE (11 total), please visit the HSDB record page.
4-Methylpyridine's production and use in the manufacture of isonicotinic acid and derivatives (such as isoniazid), in water-proofing agents for fabrics, and as a solvent for resins, pharmaceuticals, dyestuffs, rubber accelerators, and other applications(1,2) may result in its release to the environment from various waste streams(SRC). 4-Methylpyridine is also found in coal tar and in bone oil(1) as well as in cigarette smoke(3,4).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 115(SRC), determined from a structure estimation method(2), indicates that 4-methylpyridine is expected to have high mobility in soil(SRC). The pKa of 4-methylpyridine is 5.98(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 4-methylpryidine(SRC), demonstrated that Koc can vary with pH with lowest adsorption occurring in the non-ionized form(5). Volatilization of 4-methylpyridine from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 6.0X10-6 atm-cu m/mole(6). 4-Methylpyridine is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.77 mm Hg at 25 °C(7). 4-Methylpyridine may biodegrade fairly rapidly in aerobic soil; however, under anaerobic conditions, this compound is expected to be persistent(8,9). 71.7 and 100% of the available nitrogen was released as inorganic nitrogen within 16 and 32 days following the incubation of 4-methylpyridine in aerobic Fincastle silt loam(7). 4-Methylpyridine added to an unpolluted surface soil under denitrifying or sulfidogenic conditions was 40 to 50% degraded in 3 months(8). Acclimation of microbes may be important as demonstrated by complete degradation of 4-methylpyridine in 2 weeks in polluted soil versus 3 months in unpolluted soil(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 6.0X10-6 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 6 and 47 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 1.22(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 4-Methylpyridine may biodegrade fairly rapidly in aerobic waters; however, under anaerobic conditions, this compound is expected to be persistent. Complete biodegradation of 4-methylpyridine was reported in 2 to 4 days following incubation in acclimated natural waters(7). No biodegradation was reported over 200 days when 4-methylpyridine was incubated in sulfidogenic estuarine sediment(8). 4-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 4-methylpyridine in aqueous solution shows no absorption >290 nm(9); therefore, 4-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), 4-methylpyridine, which has a vapor pressure of 5.77 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-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 2.69X10-12 cu cm/molecule-sec at 25 °C(3). The UV absorption spectrum of 4-methylpyridine in aqueous solution shows no absorption >290 nm(4); therefore, 4-methylpyridine is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of 4-methylpyridine with photochemically-produced hydroxyl radicals has been measured as 2.69X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Methylpyridine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). The UV absorption spectrum of 4-methylpyridine in aqueous solution shows a UV maximum at 253 nm, but no absorption >290 nm(3); therefore, 4-methylpyridine is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated for 4-methylpyridine(SRC), using a log Kow of 1.22(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of 4-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 4-methylpyridine is 5.98(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 4-methylpryidine(SRC), demonstrated that Koc can vary with pH with lowest adsorption occurring in the non-ionized form(5). Spectral studies of 4-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(6).
The Henry's Law constant for 4-methylpyridine is 6.0X10-6 atm-cu m/mole(1). This Henry's Law constant indicates that 4-methylpyridine is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 6 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 47 days(SRC). 4-Methylpyridine's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 4-Methylpyridine is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.77 mm Hg at 25 °C(3). 4-Methylpyridine is a weak base with a pKa of 5.98(4), which indicates this compound will partially exist in the protonated form in acidic conditions, and no volatilization from water or moist soil will occur for the cation(SRC).
GROUNDWATER: 4-Methylpyridine was detected in groundwater samples near a coal gasification site near Hoe Creek in northeastern WY(1). 4-Methylpyridine was found in groundwater contaminated by wood-preserving chemicals in Pensacola, FL at the following concentrations and depths: 1.34 mg/L at 6.1 m, 0.43 mg/L at 3.3 m, 0.25 mg/L at 5.8 m, and 0 at 11.0 m(2). 4-Methylpyridine was detected in contaminated groundwater near a wood-preserving facility in Pensacola Bay, FL at a concentration of 0.1 mg/L(3). 4-Methylpyridine was identified in groundwater at Gas Works Park, Seattle, WA in one out of sixteen wells at a concentration of 1.9 mg/L(4).|DRINKING WATER: 4-Methylpyridine was listed as a contaminant found in drinking water from a survey of US cities including Pomona, Escondido, Lake Tahoe and Orange County, CA; and Dallas, TX; Washington, DC; Cincinnati, OH; Philadelphia, PA; Miami, FL; New Orleans, LA; Ottumwa, IA, and Seattle, WA(1).|SURFACE WATER: 4-Methylpyridine was detected in contaminated stream water near a wood-preserving facility in Pensacola Bay, FL at a concentration of 0.0003 mg/L(1).
4-Methylpyridine was identified as a volatile component of fried bacon(1). 4-Methylpyridine is reported in pork meat volatiles(2).
According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of 4-methylpyridine is 100 to 999; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 9,577 workers (1,118 of these were female) were potentially exposed to 4-methylpyridine in the US(1). Occupational exposure to 4-methylpyridine may occur through inhalation and dermal contact with this compound at workplaces where 4-methylpyridine is produced or used(SRC). A 1982 study showed 4-methylpyridine was emitted to the air from wastewaters at a shale oil facility exposing inside workers(2). Monitoring data indicate that the general population may be exposed to 4-methylpyridine via inhalation of ambient air, inhalation of cigarette smoke, and ingestion of food and contaminated drinking water(SRC).|The most probable routes of human exposure to 4-methylpyridine are by inhalation, dermal contact and ingestion. Atmospheric workplace exposures have been documented(1). Drinking water supplies have been shown to contain 4-methylpyridine(2).
Drug Information
It was found that 4-picoline has a shorter residence time than the other substituted picolines in the liver, brain and kidney. Elimination occurred vua a biphasic process.
Although the exact mechanism has not been determined, it appears that all methylpyridines are oxidized to their respective aromatic acids. ...Formation of an N-oxide also occurs with 4-methylpyridine.|The biotransformations of gamma-picoline were investigated in the rat. Wistar rats were admin gamma-picoline by stomach tube at a dose of 300 mg/kg body weight. Urine was collected for 24 hours in the presence of acetic acid while expired air was sampled in 5% aqueous sulfuric acid. gamma-Picoline and metabolites were extracted from the samples and characterized by chromatographic analysis and mass spectrometry. Unmetabolized gamma-picoline was identified in both expired air and 24 hour urine; excreted amounts were approx 2.5% in each. The mass spectral characteristics of gamma-picoline-N-oxide, methylisonicotinate and methylisonicotinurate in the urine were examined; excreted amounts were 1.5%, 50% and 5% respectively. The /results suggest/ that two metabolic pathways for gamma-picoline are observed: N-oxidation leads to the formation of N-oxide; and methyloxidation leads to the formation of isonicotinic acid excreted mainly unchanged and partly as the glycine conjugate isonicotinuric acid.
ACUTE/CHRONIC HAZARDS: Moderate fire risk. (NTP, 1992)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
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.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat as necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|/SRP:/ Advanced treatment: Consider orortracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonistic such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/
/SIGNS AND SYMPTOMS/ Symptoms include occasional diarrhea, weight loss, anemia, & ocular & facial paralysis.|/GENOTOXICITY/ 4-Methylpyridine induced a dose-related increased frequency of sister chromatid exchange in human lymphocyte cultures from three individuals. Chromosomal aberrations induced by 4-methylpyridine included: chromatid breaks; centromeric, intermediate & terminal chromosome breaks; terminal & interstitial deletions; translocation; dicentric chromosomes; & isochromosomes.
4-methylpyridine
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Burning sensation. 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.
4-Methylpyridine Use and Manufacturing
It is prepared by synthesis and by-product recovery from coal coking. The reaction of acetaldehyde with ammonia produces 2-methylpyridine and 4-methylpyridine. Preheat ammonia to 450°C, mix it with the gasified acetaldehyde, react at 410-430°C through a fluidized reaction tower equipped with an aluminum silicate catalyst preheated to 430°C, and the generated gas is separated and condensed , Put the obtained reaction solution into the dehydration pot, add 2% solid alkali, dehydrate at reflux at 92℃ for 2h, stand still for layering and fractional distillation, collect the fraction of 142-144℃ to obtain 4-methylpyridine. The yield is 20% based on acetaldehyde (125-130°C fraction is 2-methylpyridine). Raw material consumption quota: 1174kg/t for liquid ammonia and 3019kg/t for acetaldehyde.
manufacture of isonicotinic acid and derivatives.In waterproofing agents for fabrics.As solvent for resins.
Intermediates
(1989) ca. 1,500 t/a|Pyridine, 4-methyl- 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, 4-methyl-. Aggregated National Production Volume: 1 to < 10 million.|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Pyridine, 4-methyl-. National Production Volume: Withheld.
All other basic organic chemical manufacturing|Pyridine, 4-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. /Pyridine bases/
Absorbent & gas chromatographic methods are described for determining 4-picoline in the atmosphere of the working zone of coke furnaces.|Various TLC systems for the separation of 2-, 3-, & 4-substituted pyridines are described.
Food additives -> Flavoring Agents
Flavoring Agents
Computed Properties
Molecular Weight:93.13
XLogP3:1.2
Hydrogen Bond Acceptor Count:1
Exact Mass:93.057849228
Monoisotopic Mass:93.057849228
Topological Polar Surface Area:12.9
Heavy Atom Count:7
Complexity:46.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Recommended Suppliers of 4-Methylpyridine
-
CN
5 YRS
Business licensed Certified factoryManufactory Supplier of fine chemicals,pharmaceutical materials -
CN
4 YRS
Business licensed Certified factoryManufactory Supplier of Chemical Pesticides,Food Additives,Agrochemicals,Active Pharm Ingredients,Flavors and Fragrances,Chemical Catalyst,Chemical Materials,Chem&Pharm Intermediates,Organic Intermediates,Feed AdditiveInquiryCAS No.: 108-89-4Grade: Industrial GradeContent: 99% -
CN
5 YRS
Business licensedTrader Supplier of PVC resin,pvc paste resin,melamine
Learn More Other Chemicals
-
Benzaldehyde, 4-[(2-chloroethyl)ethylamino]-, polymer with 4-methylpyridine
71566-74-0
-
Benzaldehyde, 4-[(2-chloroethyl)ethylamino]-, polymer with 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole and 4-methylpyridine
71477-87-7
-
Penbutolol
38363-40-5
-
Xanthylium, 9-(2,4-dicarboxyphenyl)-3,6-bis(diethylamino)-, chloride, sodium salt (1:1:2) Formula
37299-86-8
-
4-(Ethylnitrosoamino)-1-butanol Formula
54897-62-0
-
3,6-Nonadien-1-ol Formula
76649-25-7
-
4-(isoquinolin-5-yldiazenyl)-N,N-dimethylaniline Structure
63040-64-2
-
5-methyl-4,4-diphenyl-6-pyrrolidin-1-ylhexan-3-one Structure
63765-89-9
-
What is 2-(methylamino)-1-phenylbutan-1-ol
63199-79-1
-
What is 2-(cyclopropanecarbonylamino)acetic acid
64513-70-8