(Dimethylamino)ethyl methacrylate
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(Dimethylamino)ethyl methacrylate
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CAS No:
2867-47-2
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Formula:
C8H15NO2
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Chemical Name:
(Dimethylamino)ethyl methacrylate
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Synonyms:
2-Propenoic acid,2-methyl-,2-(dimethylamino)ethyl ester;Methacrylic acid,2-(dimethylamino)ethyl ester;N,N-Dimethylaminoethyl methacrylate;β-Dimethylaminoethyl methacrylate;2-(Dimethylamino)ethyl methacrylate;(Dimethylamino)ethyl methacrylate;2-(N,N-Dimethylamino)ethyl methacrylate;β-(N,N-Dimethylamino)ethyl methacrylate;N,N-Dimethylethanolamine methacrylate;DM (methacrylate);DM;Light Ester DM;Acryester DM;Ageflex FA 1;Mhoromer BM 601;(2-Methacryloyloxyethyl)dimethylamine;Methacryl Ester DM;NSC 20959;Ageflex FM 1;Ageflex FM 2;Methacryloyloxyethyldimethylamine;MADAM;GE 720;Dimethyl[2-(methacryloyloxy)ethyl]amine;DMAEMA;DMA 200;Methacrylate DMA;N,N′-Dimethylamino-2-ethyl methacrylate;2-(Dimethylamino)ethyl 2-methylprop-2-enoate;2-Dimethylaminoethyl 2-methylprop-2-enoate;44919-97-3;68224-31-7;114975-29-0;124942-19-4;134946-66-0;141303-14-2;155280-46-9;303040-91-7;874217-11-5;874217-12-6;1026457-02-2;1453489-76-3;1534343-35-5;2408386-03-6
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CAS No:
Description
colourless liquid
2-dimethylaminoethyl methacrylate appears as a clear colorless liquid. Less dense than water and insoluble in water. Vapors heavier than air and corrosive to eyes and mucous membranes. May polymerize exothermically if heated or contaminated. If polymerization takes place inside a closed container, the container may rupture violently. Produces toxic oxides of nitrogen during combustion. Toxic by skin absorption, ingestion and inhalation. Used to make plastics and in textiles.|Liquid|COLOURLESS-TO-LIGHT-YELLOW LIQUID.
2-dimethylaminoethyl methacrylate appears as a clear colorless liquid. Less dense than water and insoluble in water. Vapors heavier than air and corrosive to eyes and mucous membranes. May polymerize exothermically if heated or contaminated. If polymerization takes place inside a closed container, the container may rupture violently. Produces toxic oxides of nitrogen during combustion. Toxic by skin absorption, ingestion and inhalation. Used to make plastics and in textiles.
(Dimethylamino)ethyl methacrylate Basic Attributes
157.210
157.21
220-688-8
O0V97PV2G1
0450
20959
2522
DTXSID1027504
Liquid|Colorless liquid
2922199090
Characteristics
29.54000
1.50
2-dimethylaminoethyl methacrylate appears as a clear colorless liquid. Less dense than water and insoluble in water. Vapors heavier than air and corrosive to eyes and mucous membranes. May polymerize exothermically if heated or contaminated. If polymerization takes place inside a closed container, the container may rupture violently. Produces toxic oxides of nitrogen during combustion. Toxic by skin absorption, ingestion and inhalation. Used to make plastics and in textiles.
0.933 g/cm3 @ Temp: 25 °C
-30 °C
182-190 °C
70.6±0.0 °C
1.444
Less dense than water and insoluble in water.
... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid and derivatives/
<1 mm Hg ( 25 °C)
Relative vapour density (air = 1): 5.4
LD50 orally in Rabbit: 1751 mg/kg
Explosive limits , vol% in air: 1.2-?
Amine-like
Henry's Law constant: 1.44X10-7 atm cu m/mol at 25 °C (est)
pKa = 8.44 at 25 °C
Most aliphatic amines have an unpleasant, fishy or fishlike odor and in high concentrations they all have the odor of ammonia. /Aliphatic amines/|Hydroxyl radical reaction rate constant: 9.9X10-11 cu cm/molecule-sec at 25 °C (est)
Insoluble in water.
Amines, Phosphines, and Pyridines
Polymerizable
2-DIMETHYLAMINOETHYL METHACRYLATE is both an amine and an acrylate ester. 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. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
255 °C
48.8 kJ/mol
Safety Information
II
6.1
UN 2522 6.1/PG 2
1
R21/22;R36/38;R43
S26-S28-S2
OZ4200000
Xi:Irritant
Separated from metals, oxidants, strong reducing agents and food and feedstuffs. Keep in the dark. Store only if stabilized. Store in an area without drain or sewer access.
Stable. Incompatible with strong acids, strong bases, strong oxidizing or reducing agents. May decompose on exposure to air and moisture. May undergo autopolymerization. Light sensitive.
P301 + P312 + P330-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338-P333 + P313
H302 + H312-H314-H317
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 quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and 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.
Excerpt from ERG Guide 153P [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 68 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree, Reactive - 1st degree
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Danger|H302 (95.53%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P272, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P405, and P501|Aggregated GHS information provided by 1074 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P201, P202, P210, P260, P261, P264, P270, P272, P273, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P322, P330, P333+P313, P363, P370+P378, P403+P235, P405, and P501|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P271, P280, P284, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P363, P403+P233, P405, and P501|P201, P202, P210, P260, P261, P264, P270, P271, P280, P281, P284, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 153P [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. 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)
Excerpt from ERG Guide 153P [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Excerpt from ERG Guide 153P [Substances - Toxic and/or Corrosive (Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|Skin protection: Handle with gloves.|Eye/face protection: Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|SUITABLE PROTECTIVE CLOTHING & SELF-CONTAINED RESP PROTECTIVE APPARATUS SHOULD BE AVAILABLE FOR USE OF THOSE WHO MAY HAVE TO RESCUE PERSONS OVERCOME BY FUMES. /ACRYLIC ACID & DERIVATIVES/
Combustible|Flammable when exposed to sparks, heat, open flame, or oxidizers.
Explosive limits , vol% in air: 1.2-?
Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.|Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|To fight fire, use alcohol foam, dry chemical, spray.
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to form explosive concentrations. Vapours can accumulate in low areas.; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. 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.
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.|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.|... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/|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.
/GUIDE 153P SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.|/GUIDE 153P SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Health: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 153P SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 153P SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for N,N-DIMETHYLAMINOETHYL METHACRYLATE (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. 2-Dimethylaminoethyl methacrylate is included on the dangerous goods list.|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. 2-Dimethylaminoethyl methacrylate is included on the dangerous goods list.
Irritating to skin, eyes, and mucous membranes.
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. 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.
Separated from metals, oxidants, strong reducing agents and food and feedstuffs. Keep in the dark. Store only if stabilized. Store in an area without drain or sewer access.
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
The substance is corrosive to the eyes and skin. The substance is irritating to the respiratory tract. Corrosive on ingestion.
NO open flames. Above 68 °C use a closed system and ventilation.
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.
| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual 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.
Toxicity
IDENTIFICATION AND USE: N,N-dimethylaminoethyl methacrylate is a colorless liquid with amine-like odor.It is used in binders for coatings, textile chemicals, dispersing agents for nonaqueous systems, antistatic agents, stabilizers for chlorinated polymers, ion exchange resins, emulsifying agents, cationic precipitating agents. It is also used in dental materials, antithrombogenic prosthetics, experimental use in slow-release capsules, in cosmetics. More recently, It is also used in nanoparticles for gene delivery and drug delivery. HUMAN EXPOSURE AND TOXICITY: pH-Sensitive poly(N,N-dimethylaminoethyl methacrylate (DMAEMA)/2-hydroxyethyl methacrylate (HEMA)) nanoparticles were not cytotoxic. ANIMAL STUDIES: Dimethylaminoethyl methacrylate decreased the heart rate and force of contraction of isolated, perfused rabbit heart when added to perfusing liquid. Dimethylaminoethyl methacrylate was strongly irritating to skin of guinea pigs and conjunctiva of rabbits. When administered by gastric gavage to rabbits, dimethylaminoethyl methacrylate initially suppressed brain electrical activity and then induced clonic-tonic spasms. In dogs it produced hypertensive effect following iv administration. The toxicity of 6 acrylates and 6 methacrylates, including N,N-dimethylaminoethyl methacrylate, was determined in rats and fish. All the esters were less toxic than acrylamide and acrylonitrile.
LD50 Rat oral >2000 mg/kg bw|LD50 Rat oral 1751 mg/kg bw|LD50 Rat oral 2659 mg/kg bw|LD50 Rat oral 1550 mg/kg bw|For more Non-Human Toxicity Values (Complete) data for N,N-DIMETHYLAMINOETHYL METHACRYLATE (7 total), please visit the HSDB record page.
N,N-Dimethylaminoethyl methacrylate's production and use as an intermediate for chemical synthesis and as a monomer in the production of a variety of polymers for water treatment, paper agents, paints, coatings and personal care products(1,2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that N,N-dimethylaminoethyl methacrylate is expected to have very high mobility in soil(SRC). The pKa of N,N-dimethylaminoethyl methacrylate is 8.44(3), indicating that this compound will exist mostly in 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 N,N-dimethylaminoethyl methacrylate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(2). N,N-Dimethylaminoethyl methacrylate is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.72 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Using the OECD 301E test, 95.3% degradation was reached in 2 weeks(5) suggesting that biodegradation is an important environmental fate process in soil(SRC). Based on results of the Japanese MITI test which noted abiotic hydrolysis during biodegradation studies(5,6), N,N-dimethylaminoethyl methacrylate may degrade via abiotic hydrolysis in moist alkaline and neutral soils(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that N,N-dimethylaminoethyl methacrylate 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 1.4X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 2.6(SRC), from a log Kow of 1.13(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Using the OECD 301E test, 95.3% degradation was reached in 2 weeks(5) suggesting that biodegradation is an important environmental fate process in water(SRC). The hydrolysis half-life of N,N-dimethylaminoethyl methacrylate at 25 °C was determined to be 4.54 days and 3.31 hours at pH 7 and pH 9 respectively(5); the compound is stable to hydrolysis at pH 4(5). N,N-Dimethylaminoethyl methacrylate is an olefin and olefins in surface waters exposed to sunlight have a half-life on of 25 days(6) .|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N-dimethylaminoethyl methacrylate, which has an estimated vapor pressure of 0.72 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N,N-dimethylaminoethyl methacrylate 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 3.9 hours(SRC), calculated from its rate constant of 9.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Vapor-phase N,N-dimethylaminoethyl methacrylate is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 24 hours(SRC), calculated from its rate constant of 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Based on analogy to a measured nitrate radical rate constant of 4.90X10-15 cu cm/molecule-sec at 25 °C for ethyl methacrylate(3), the atmospheric half-life of N,N-dimethylaminoethyl methacrylate is estimated to be about 6.5 days(SRC).
The rate constant for the vapor-phase reaction of N,N-dimethylaminoethyl methacrylate with photochemically-produced hydroxyl radicals has been estimated as 9.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of N,N-dimethylaminoethyl methacrylate with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 24 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). Based on analogy to a measured nitrate radical rate constant of 4.90X10-15 cu cm/molecule-sec at 25 °C for ethyl methacrylate(2), the atmospheric half-life of N,N-dimethylaminoethyl methacrylate is estimated to be about 6.5 days(SRC) at an atmospheric concentration of 2.5X10+8 nitrate radicals per cu cm(3). N,N-Dimethylaminoethyl methacrylate is an olefin and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(4). Using OECD Guideline 111 (Hydrolysis as a Function of pH), the hydrolysis half-life of N,N-dimethylaminoethyl methacrylate at 25 °C was determined to be 4.54 days and 3.31 hours at pH 7 and pH 9, respectively(5,6). Preliminary tests at 50 °C and pH 4 found N,N-dimethylaminoethyl methacrylate stable to hydrolysis with a half-life of >1 year(6). The hydrolysis degradation products were identified as N,N-dimethyl-N-ethanolamine (CAS 108-01-0) and methacrylic acid (CAS 79-41-4)(6).
An estimated BCF of 2.6 was calculated in fish for N,N-dimethylaminoethyl methacrylate(SRC), using a log Kow of 1.13(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 N,N-dimethylaminoethyl methacrylate can be estimated to be 20(SRC). According to a classification scheme(2), this estimated Koc value suggests that N,N-dimethylaminoethyl methacrylate is expected to have very high mobility in soil. The pKa of N,N-dimethylaminoethyl methacrylate is 8.44(3), indicating that this compound will exist mostly 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).
The Henry's Law constant for N,N-dimethylaminoethyl methacrylate is estimated as 1.4X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that N,N-dimethylaminoethyl methacrylate is expected to be essentially nonvolatile from water surfaces(2). N,N-Dimethylaminoethyl methacrylate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). N,N-Dimethylaminoethyl methacrylate is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.72 mm Hg(SRC), determined from a fragment constant method(1).
According to the 2012 TSCA Inventory Update Reporting data, 5 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of N,N-dimethylaminoethyl methacrylate (2867-47-2) may be as low as 10-24 workers up to the range of 100-499 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 10,637 workers (429 of these were female) were potentially exposed to N,N-dimethylaminoethyl methacrylate in the US(1). Occupational exposure to N,N-dimethylaminoethyl methacrylate may occur through inhalation and dermal contact with this compound at workplaces where N,N-dimethylaminoethyl methacrylate is produced or used(SRC). The general population may be exposed to N,N-dimethylaminoethyl methacrylate via dermal contact with consumer products containing polymers made with the compound and resulting migration of residual monomer from the polymer matrix(2).
Drug Information
Materials that add an electron to an element or compound, that is, decrease the positiveness of its valence. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) (See all compounds classified as Reducing Agents.)
2-(Dimethylamino)ethyl methacrylate was rapidly hydrolyzed to methacrylic acid (CAS 79-41-4) and N,N,-dimethylaminoethanol (CAS 108-01-0) when incubated with simulated saliva or simulated intestinal fluid in vitro, but not with simulated gastric fluid.. 90% degradation was observed in simulated saliva after 4 hours at 37 °C, 86% degradation after incubation with simulated intestinal fluid for 4 hours at 37 °C. Degradation was below 8% after incubation with simulated gastric fluid for 4 hours at 37 °C.
Excerpt from ERG Guide 153P [Substances - Toxic and/or Corrosive (Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)
Excerpt from ERG Guide 153P [Substances - Toxic and/or Corrosive (Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)
Fresh air, rest.
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. /Esters 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 ventilation 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 ... . 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 ... . /Esters and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal 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 ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /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. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/
/OTHER TOXICITY INFORMATION/ pH-Sensitive poly(N,N-dimethylaminoethyl methacrylate (DMAEMA)/2-hydroxyethyl methacrylate (HEMA)) nanoparticles were prepared for the triggered release of paclitaxel within a tumor microenvironment. Tumors exhibit a lower extracellular pH than normal tissues. We show that paclitaxel release from DMAEMA/HEMA particles can be actively triggered by small, physiological changes in pH (within 0.2-0.6 pH units). Monodispersed nanoparticles were synthesized by forming an O/W emulsion followed by photopolymerization. Particles were characterized by transmission electron microscopy, dynamic light scattering, electrophoresis, and cytotoxicity. High release rates and swelling ratios are achieved at low pH, low crosslinking density, and high content of DMAEMA. Paclitaxel release is limited to 9% of the payload at pH 7.4 after a 2-hr incubation at 37 degrees C. After adjusting to pH 6.8, 25% of the payload is released within 2 hr. Cell viability studies indicate that pH-sensitive DMAEMA/HEMA nanoparticles are not cytotoxic and may be used as an efficient, feedback-regulated drug delivery carrier. /Poly(N,N-dimethylaminoethyl methacrylate/
2-(dimethylamino)ethyl methacrylate
Cough. Sore throat.
Skin burns. Pain.
Redness. Pain. Severe deep burns.
(Dimethylamino)ethyl methacrylate Use and Manufacturing
The methacrylates can be synthesized by catalytic oxidation of isobutylene and subsequent esterification with the appropriate alcohol, or by reacting acetone with hydrocyanic acid and subsequent esterification in sulfuric acid with the appropriate alcohol. /Methacrylic esters/|Transesterification or esterification of dimethylaminoethanol with methyl methacrylate or methacrylic acid.
N,N-Dimethylaminoethyl-methacrylate is an amine activator in visible-light-cured dental-acrylic composite materials.
Intermediates
10,000,000 - 50,000,000 lb|(1979) 1.00X10+9 G|(1981) 1.29X10+9 G|2-Propenoic acid, 2-methyl-, 2-(dimethylamino)ethyl ester 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).|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2-Propenoic acid, 2-methyl-, 2-(dimethylamino)ethyl ester. National Production Volume: 10,000,000 - 50,000,000 lb/yr.
2-Propenoic acid, 2-methyl-, 2-(dimethylamino)ethyl ester, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|All other basic organic chemical manufacturing|2-Propenoic acid, 2-methyl-, 2-(dimethylamino)ethyl ester: ACTIVE|Methyl methacrylate, and in general the methacrylic esters, polymerize much less readily than the corresponding ordinary acrylates. None the less, they are stabilized by adding hydroquinone or pyrogallol, particularly in the presence of metallic copper. /Methacrylates/
Thin-layer chromatography (TLC), polarography, and spectrometry are used for solution measurements. Methacrylates in air have been analyzed by TLC, polarography, and colorimetry. Polarography has been used for determination of any residual monomer in the polymer. A variety of spectroscopic techniques, e.g., NMR, IR, and Raman spectroscopy also have been used, particularly for analysis of surgical cements and dental restorative resins. /Methacrylic acid and derivatives/|THE ELECTRON-IMPACT AND METHANE CHEM-IONIZATION MASS SPECTRA OF SELECTED ACRYLATE AND METHACRYLATE MONOMERS, INCLUDING DIMETHYLAMINOETHYL METHYACRYLATE, COMMONLY USED IN DENTAL MATERIALS ARE REPORTED AND DISCUSSED. THE TWO IONIZATION MODES COMPLEMENT EACH OTHER, AND TOGETHER THE MASS SPECTRA OFFER ADEQUATE INFORMATION FOR IDENTIFICATION PURPOSES. THE APPLICATION OF THE MASS SPECTRAL METHOD IS DEMONSTRATED ON RESIN-BASED DENTAL MATERIALS WITH IDENTIFICATION OF THE MONOMER CONTENT.
Fire Hazards -> Flammable - 2nd degree, Reactive - 1st degree|Cosmetics -> Viscosity controlling
Computed Properties
Molecular Weight:157.21
XLogP3:1.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:157.110278721
Monoisotopic Mass:157.110278721
Topological Polar Surface Area:29.5
Heavy Atom Count:11
Complexity:152
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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