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2-Methylaminoethanol
2-(METHYLAMINO)ETHANOL · N-METHYLETHANOLAMINE · Ethanol, 2-(methylamino)- · Methylethanolamine · N-Methylaminoethanol · Methylaminoethanol · METHYLETHYLOLAMINE · 2-(N-Methylamino)ethanol
Identifikatoren & physikalische Daten
| CAS No. | 109-83-1 |
|---|---|
| Summenformel | C3H9NO |
| Durchschnittliche Molmasse | 75,11 g/mol |
| Monoisotopische Masse | 75,06841391 g/mol |
| SMILES | CNCCO |
| InChIKey | OPKOKAMJFNKNAS-UHFFFAOYSA-N |
| PubChem CID | 8016 |
| ChEMBL | CHEMBL104083 |
| ChEBI | CHEBI:21763 |
| EC No. | 203-710-0 |
| DTXSID | DTXSID5025603 |
| Lokaler Name | 2-Methylaminoethanol |
Chemische & physikalische Eigenschaften
| XLogP | -0,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 32,3 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 16,4 |
| Stoffklassen | Nitrogen Compounds -> EthanolaminesCorrosives |
| Kosmetika | Buffering |
| pH | A strong base13.6 (100g/l, H2O, 20℃) |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | log Kow = -0.94 |
| Geruch | Fishy |
| Dichte | 0.9414 (USCG, 1999) - Less dense than waterwill float0.937 g/cu cm at 20 °CRelative density (water = 1): 0.930.937 @ 20°C0.935 g/mL at 25 °C(lit.) |
| Viscosity | 13.0 mPa s at 20 °C |
| Color/Form | Viscous liquidClear colorless liquidColorless to light yellow liquid |
| Löslichkeit | Very soluble (NTP, 1992)Miscible with alcohol, etherIn water, 1X10+6 mg/L (miscible)Solubility in water: miscibleChloroform (Soluble), Methanol (Slightly) |
| Corrosivity | Corrosive to cork, metals |
| Flammpunkt | 165 °F (NTP, 1992)73.9 °C76 °C (169 °F) - closed cup165 °F (74 °C) (Open cup)74 °C o.c.163 °F |
| Schmelzpunkt | -3 °C |
| Siedepunkt | 159 °C(lit.) |
| Dampfdichte | 2.6 (vs air) |
| Dampfdruck | 0.5 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.439(lit.) |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | pK1:9.88(+1) (25°C) |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to slightly yellow |
| Explosionsgrenze | 1.6-17.7%(V) |
| Merck | 14,6015 |
| BRN | 1071196 |
| Henry-Konstante | 9.0×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Combustible. Incompatible with oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | BUFFERING |
| InChI | 1S/C3H9NO/c1-4-2-3-5/h4-5H,2-3H2,1H3 |
| InChIKey | OPKOKAMJFNKNAS-UHFFFAOYSA-N |
| SMILES | CNCCO |
| LogP (Verteilungskoeffizient) | -0.91 at 25℃ |
| Oberflächenspannung | 35.68mN/m at 293.15K |
| CAS Datenbank | 109-83-1(CAS DataBase Reference) |
| NIST chemische Informationen | Ethanol, 2-(methylamino)-(109-83-1) |
| EPA chemische Informationen | N-Methylethanolamine (109-83-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Ethanol, 2-(methylamino)-Ethanol, 2-(methylamino)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-(methylamino)- 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: 24-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/139122-(Methylamino) ethanol: 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.) |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| DOT-Kennzeichnung | Corrosive |
| Brandgefahren | Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as nitrogen oxides and carbon monoxide, may be formed when involved in fire. (USCG, 1999)Combustible. Above 74 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Flammable when exposed to heat, flame, or oxidizers. |
| Gesundheitsgefahren | Exposure can cause irritation of eyes, nose and throat. (USCG, 1999) |
| Gefahrenübersicht | A corrosive substance that can cause injury to the skin, eyes, and respiratory tract[ICSC] Not teratogenic in one study of rats receiving a vaporized dose of 150 ppm 7 hours/day during gestation days 7-15. [REPROTOX] May be absorbed through skinEffects in high-dose animal studies include seizures and coma[MSDSonline] |
| Reaktive Gruppe | Alcohols and Polyols |
| EG-Einstufung | Symbol: CR: 21/22-34S: (1/2)-26-36/37/39-45 |
| Reactivity Profile | METHYLETHANOLAMINE is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. This compound may react with oxidizing materials. (NTP, 1992) |
| Chemical Dangers | Decomposes on burning. This produces toxic fumes including nitrogen oxides. The substance is a strong base. It reacts violently with acid and is corrosive. Reacts with strong oxidants. Attacks many metals. |
| Air and Water Reactions | Soluble in water. |
| Brandbekämpfung | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Artificial respiration may be needed. 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 . |
| Erste Hilfe | 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. |
| Sichere Lagerung | Separated from strong oxidants and acids. |
| Brandbekämpfungsverfahren | 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.Use water spray to cool unopened containers.To fight fire, used alcohol foam. |
| Lagerbedingungen | 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. Storage class (TRGS 510): Combustible, corrosive hazardous materials.Separated from strong oxidants and acids. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. 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. Discharge into the environment must be avoided. 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. Keep in suitable, closed containers for disposal.Collect leaking and spilled liquid in sealable containers as far as possible. Cautiously neutralize remainder. Then wash away with plenty of water. |
| Freisetung ohne Brand | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Entsorgungsverfahren | SRP: 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 qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal companyContaminated packaging: Dispose of as unused product. |
| Verschüttetes entsorgen | Personal protection: complete protective clothing including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Cautiously neutralize remainder. Then wash away with plenty of water. |
| Preventive Measures | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. 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. Discharge into the environment must be avoided.Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.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.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. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2-methylaminoethanol is expected to have very high mobility in soil(SRC). The pKa of 2-methylaminoethanol is 9.95(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of the neutral species of 2-methylaminoethanol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.1X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(2). 2-Methylaminoethanol is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.08 mm Hg at 25 °C(5). A 68% of theoretical BOD using activated sludge in the Japanese MITI test classifies 2-methylaminoethanol as readily biodegradable(6) and suggests that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2-methylaminoethanol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 8.1X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). The pKa of 2-methylaminoethanol is 9.95(4), indicating that this compound will exist almost entirely in cation form in the environment, and volatilization from water is unlikely since cations do not volatilize(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of -0.94(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 68% of theoretical BOD using activated sludge in the Japanese MITI test classifies 2-methylaminoethanol as readily biodegradable(7) and suggests that biodegradation is an important environmental fate process in water(SRC). Hydrolysis is not expected to be an important environmental fate process(SRC) since this compound lacks functional groups that hydrolyze under environmental conditions(3).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-methylaminoethanol, which has a vapor pressure of 1.08 mm Hg at 25 °C (2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-methylaminoethanol 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 4.9 hours(SRC), calculated from its rate constant of 7.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Methylaminoethanol does not contain chromophores that absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight(4). |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion. |
| Toxizitätsübersicht | IDENTIFICATION AND USE: 2-Methylaminoethanol is a viscous liquid. It is used in the manufacture of textile chemicals, pharmaceuticals. HUMAN EXPOSURE AND TOXICITY: Prolonged hematuria, pathologic liver function tests, and multiple skin warts described in a patient after 2-methylaminoethanol exposure. ANIMAL STUDIES: In rats it was irritating to the skin, eyes, and mucous membranes. 2-Methylaminoethanol (150 ppm) was not maternally toxic or embryotoxic in rats. It was not mutagenic in S. typhimurium TA 1535, TA 1537, TA 98 and TA 100 with and without metabolic activation. |
| Signs and Symptoms | Sore throat. Cough. Burning sensation. Shortness of breath. Laboured breathing. Symptoms may be delayed.Pain. Redness. Blisters. Skin burns.Pain. Redness. Severe deep burns. Loss of vision.Burning sensation. Abdominal pain. Shock or collapse. |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. 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/[USEPAICSS Dashboard ApplicationAvailable from, as of December 8, 2016: http://actor.epa.gov/dashboard/]The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for N-methylethanolamine is available.[Available from, as of March 24, 2017: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status] |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-methylaminoethanol can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-methylaminoethanol is expected to have very high mobility in soil. The pKa of 2-methylaminoethanol is 9.95(3), indicating that this compound will exist almost entirely in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ /Inhalation causes:/ sore throat, cough, burning sensation, shortness of breath, labored breathing, symptoms may be delayed./SIGNS AND SYMPTOMS/ /Skin exposure causes/ pain, redness, blisters, skin burns./SIGNS AND SYMPTOMS/ /Eye exposure causes/ pain, redness, severe deep burns, loss of vision./SIGNS AND SYMPTOMS/ /Ingestion causes/ burning sensation, abdominal pain, shock or collapse./CASE REPORTS/ ... This report presents a patient who during exposure to 2-methylaminoethanol developed prolonged hematuria, pathologic liver function tests, and multiple skin warts. |
| Artificial Pollution Sources | 2-Methylaminoethanol's production and use as an intermediate in the synthesis of numerous products that include coatings, textile lubricants, polishes, detergents, pesticides, personal care products, and pharmaceuticals(1) may result in its release to the environment through various waste streams(SRC). 2-Methylaminoethanol is reportedly used in hydraulic fracturing fluids which releases the compound directly to the environment(2). |
| Environmental Biodegradation | AEROBIC: 2-Methylaminoethanol, present at 100 mg/L, reached 68% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test, which classified the compound as readily biodegradable(1). |
| Environmental Bioconcentration | An estimated BCF of 3 was calculated in fish for 2-methylaminoethanol(SRC), using a log Kow of -0.94(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). |
| Volatilization from Water/Soil | The Henry's Law constant for 2-methylaminoethanol is estimated as 8.1X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-methylaminoethanol is expected to be essentially nonvolatile from water surfaces(2). The pKa of 2-methylaminoethanol is 9.95(3), indicating that this compound will exist almost entirely in cation form in the environment, and volatilization from water applies to the neutral species since cations do not volatilize(SRC). 2-Methylaminoethanol's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur for the neutral species(SRC). 2-Methylaminoethanol is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.08 mm Hg at 25 °C(4). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2735 8/PG 2 |
| Zollcode | 29221980 |
| RTECS-Nr. | KL6650000 |
| R-Sätze (R) | 21/22-34-48/22 |
| Toxizität | LD50 orally in Rabbit: 1391 mg/kg LD50 dermal Rabbit 1006 mg/kg |
| Gefahrensymbole | C |
| Sicherheitshinweise (S) | 26-36/37/39-45 |
| Gefahrenklasse | 8Acute Tox. 4 DermalAcute Tox. 4 OralEye Dam. 1Repr. 2Skin Corr. 1BSTOT RE 2 OralSTOT SE 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
| Gefahrstoffdaten | 109-83-1(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 662 °F |
Anwendungen & Verwendung
Verwenden
Textile chemicals, pharmaceuticals.
Verwenden
2-Methylaminoethanol is used as an intermediate in synthetic chemistry. It finds application in various fields such as textile lubricants, polishes, detergents and in personal care products. It is also involved in electrostatic automotive coatings and in acid gas scrubbing. Further, it serves as an intermediate in polymers and pharmaceuticals. In addition to this, it is used as a solvent in the natural gas-processing industry.