HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
5-Ethyl-2-methylpyridin
2-METHYL-5-ETHYLPYRIDINE · FEMA 3546 · 5-ETHYL-2-PICOLINE · 5-Ethyl-2-Methylpyridne · Pyridine, 5-ethyl-2-methyl- · NSC 1984 · -2-picoL · ALDEHYDINE
Identifikatoren & physikalische Daten
| CAS No. | 104-90-5 |
|---|---|
| Summenformel | C8H11N |
| Durchschnittliche Molmasse | 121,18 g/mol |
| Monoisotopische Masse | 121,08914935 g/mol |
| SMILES | CCc1ccc(C)nc1 |
| InChIKey | NTSLROIKFLNUIJ-UHFFFAOYSA-N |
| PubChem CID | 7728 |
| ChEMBL | CHEMBL227181 |
| ChEBI | CHEBI:179423 |
| EC No. | 203-250-0 |
| DTXSID | DTXSID7021861 |
| Lokaler Name | 5-Ethyl-2-methylpyridin |
Chemische & physikalische Eigenschaften
| XLogP | 2 |
|---|---|
| Polarare Oberfläche (TPSA) | 12,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 80,6 |
| Stoffklassen | Nitrogen Compounds -> PyridinesCorrosives |
| SpringerMaterials Properties | Composition |
| LogP (Verteilungskoeffizient) | 2.39 |
| Geruch | Sharp, penetrating odorStrong aromatic odor |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.922 at 68 °F (USCG, 1999) - Less dense than waterwill floatSpecific gravity: 0.9184 @ 23 °C/4 °CDensity (at 20 °C): 0.92 g/cm³Relative density of the vapour/air-mixture at °C (air = 1): 1.010.917-0.9230.919 g/mL at 25 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | Colorless liquid |
| Löslichkeit | Sol in alc, ether, benzene, dilute acids, concn sulfuric acidVery soluble in acetoneIn water, 1.2 g/100 ml @ 29 °C12 mg/mL at 20 °CSolubility in water, g/l at 20 °C: 12 (moderate)Slightly soluble in water and fat12.0g/lpractically insoluble |
| Flammpunkt | 155 °F (USCG, 1999)68 °C155 °F, 68 °C (OPEN CUP)68 °C o.c.151 °F |
| Siedepunkt | 352 °F at 760 mmHg (USCG, 1999)177.8 °C @ 747 mm Hg172.00 to 175.00 °C. @ 760.00 mm Hg178.3 °C172-175 °C178 °C (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke & irritating fumes. |
| Schmelzpunkt | -70.9 °C |
| Dampfdichte | 4.2 (vs air) |
| Dampfdruck | 1.853hPa at 20℃ |
| Brechungsindex | n20/D 1.497(lit.) |
| FEMA | 3546 | 5-ETHYL-2-METHYLPYRIDINE |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | pK1:6.51(+1) (20°C) |
| Aggregatzustand | clear liquid |
| Farbe | Colorless to Light orange to Yellow |
| Wichte | 0.921 (20/4℃) |
| Geruch | at 0.10 % in propylene glycol. nutty strong raw potato roasted earthy |
| Geruchsart | nutty |
| Biologische Quelle | synthetic |
| Merck | 14,3844 |
| JECFA Number | 1318 |
| BRN | 109269 |
| Henry-Konstante | 5.2×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. Hygroscopic. Combustible. Incompatible with strong oxidizing agents. |
| InChI | 1S/C8H11N/c1-3-8-5-4-7(2)9-6-8/h4-6H,3H2,1-2H3 |
| InChIKey | NTSLROIKFLNUIJ-UHFFFAOYSA-N |
| SMILES | CCc1ccc(C)nc1 |
| LogP (Verteilungskoeffizient) | 2.1 at 22℃ |
| CAS Datenbank | 104-90-5(CAS DataBase Reference) |
| NIST chemische Informationen | Pyridine, 5-ethyl-2-methyl-(104-90-5) |
| EPA chemische Informationen | 5-Ethyl-2-methylpyridine (104-90-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302 (> 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.H227: Combustible liquid [Warning Flammable liquids] |
|---|---|
| Regulatorische Informationen | 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/101745-Ethyl-2-picoline: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | 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. |
| Brandpotenzial | Flammable when exposed to heat or flame ... . |
| Gesundheitsgefahren | Breathing of vapors will cause vomiting and chest discomfort. Contact with liquid causes skin and eye burns. (USCG, 1999)· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| Gefahrenübersicht | Emergency treatment: PyridinePyridine is an irritant that causes CNS depression after ingestion of 1/2 cup or inhalation of 6-12 ppmIt 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 burnsHarmful by inhalation or ingestion[Aldrich MSDS] See Pyridine. |
| DOT-Nummer und Handbuch | 2300 153 |
| Reaktive Gruppe | Amines, Phosphines, and Pyridines |
| EG-Einstufung | Symbol: CR: 20/21/22-43-34S: 26-28-36/37/39 |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: III |
| Reactivity Profile | 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]. |
| Chemical Dangers | On combustion, forms irritating and toxic fumes including nitrogen oxides and carbon monoxide. Reacts vigorously with strong oxidants. This generates fire and explosion hazard. Attacks copper and copper alloys. |
| Brandbekämpfung | 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. |
| Erste-Hilfe-Maßnahmen | 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. |
| Freisetungsmaßnahmen | · 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. |
| Erste Hilfe | INHALATION: remove victim to fresh airgive oxygen if breathing is difficultcall a physician.General First Aid: |
| Sichere Lagerung | Keep in a well-ventilated room. Store in an area without drain or sewer access. Separated from food and feedstuffs and strong oxidants. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Freisetung ohne Brand | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Entsorgungsverfahren | 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. |
| Verschüttetes entsorgen | 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. |
| Preventive Measures | 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Immediate precautionary measure |
| Eye Prevention | Wear safety goggles or face shield. |
| Ökotoxizitätswerte | 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. |
| Umweltverhalten | 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). |
| Lebensmitteluntersuchungswerte | 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). |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Expositionspfade | The substance can be absorbed into the body by inhalation, by ingestion and through the skin. |
| Signs and Symptoms | Cough. Sore throat.Redness. Pain. Skin burns.Sore throat. Burning sensation behind the breastbone. Abdominal pain. |
| Effluent Concentrations | 2-Methyl-5-ethylpyridine was detected in 1 of 21 industrial categories of wastewater effluents(1). Extract from the wastewater of an organic chemical manufacturer contained 2-methyl-5-ethylpyridine at an average concn of 3021 mg/l(1,2). |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Soil Adsorption/Mobility | 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). |
| TSCA Test Submissions | 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. |
| Natural Pollution Sources | 5-Ethyl-2-methyl-pyridine was found in peppermint oils. |
| Artificial Pollution Sources | 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). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2300 |
| Zollcode | 29333990 |
| RTECS-Nr. | TJ6825000 |
| R-Sätze (R) | 20/22-34-20/21/22-52/53 |
| Gefahrensymbole | C,N |
| hazard_note | Corrosive |
| Sicherheitshinweise (S) | 26-36/37/39-45-61 |
| Gefahrenklasse | 6.1Acute Tox. 3 DermalAcute Tox. 4 OralEye Dam. 1Skin Corr. 1B |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 104-90-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Occurrence
Reported in dry red beans, cocoa, tea, whiskey, peppermint oil, roasted and fried chicken, cocoa, coffee and cooked shrimps.
Verwenden
5-Ethyl-2-methylpyridine is used as specific solvent and as intermediate for several chemical reactions. Attributes PIS available on request. Please contact us. Contact
Herstellung & Synthese
synthetische
Prepared by heating acetaldehyde ammonia in a double volume of absolute alcohol; by heating ammonia water and paraldehyde in presence of ammonium acetate.