2-(Diisopropylamino)ethyl methacrylate

213.31700

213.32

240-772-8

QQQ3B8K5K1

DTXSID5066110

Liquid

2922199090

29.54000

2.22450

0.915g/cm3

266.7ºC at 760mmHg

83.6ºC

1.45

In water, 1580 mg/L at 25 °C (est)

Conditions for safe storage, including any incompatibilities: 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. Recommended storage temperature: 2 - 8 °C|Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... 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/

0.0085mmHg at 25°C

Henry's Law constant: 3X10-7 atm cu m/mol at 25 °C (est)

pKa = 9.53 at 25 °C (est)

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: 1.3X10-10 cu cm/molecule-sec at 25 °C (est)

Stable under recommended storage conditions.

P261; P280; P305 + P351 + P338

H315; H317; H318; H335

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.|Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx)

Incompatible materials: Strong oxidizing agents, Catalysts, Rust, Steel (all types and surface treatments), Copper, Water

|Danger|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P333+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315: Causes skin irritation [Warning Skin corrosion/irritation]

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).|Body Protection: Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|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).

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.|Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas.; Environmental precautions: Do not let product enter drains.; Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. 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.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapour or mist. Normal measures for preventive fire protection.

Methacrylates ... produce slight to moderate skin and eye irritation ... depending upon volatility, these materials also may be sensory irritants. /Methacrylic acid & derivatives/

IDENTIFICATION AND USE: 2-(Diisopropylamino)ethyl methacrylate is a liquid with an unpleasant, fishy or fishlike odor and in high concentrations the odor of ammonia. It used as comonomer for polymers and acrylic resins. It is also used as a component of polymersomes which offer a novel drug delivery system for the effective delivery of chemotherapeutics. HUMAN EXPOSURE AND TOXICITY: There is no data available. ANIMAL STUDIES: Diisopropylaminoethyl methacrylate was weakly irritating to skin of guinea pigs and conjunctiva of rabbits.

Photodynamic therapy is an effective treatment for tumors that involves the administration of light-activated photosensitizers. However, most photosensitizers are insoluble and non-specific. To target the acid environment of tumor sites, we synthesized three poly(ethylene glycol) methacrylate-co-2-(diisopropylamino)ethyl methacrylate (PEGMA-co-DPA) copolymers capable of self-assembly to form pH sensitive nanoparticles in an aqueous environment, as a means of encapsulating the water-insoluble photosensitizer, meso-tetra(hydroxyphenyl)chlorin (m-THPC). The critical aggregation pH of the PEGMA-co-DPA polymers was 5.8-6.6 and the critical aggregation concentration was 0.0045-0.0089 wt% at pH 7.4. Using solvent evaporation, m-THPC loaded nanoparticles were prepared with a high drug encapsulation efficiency (approximately 89%). Dynamic light scattering and transmission electron microscopy revealed the spherical shape and 132 nm diameter of the nanoparticles. The in vitro release rate of m-THPC at pH 5.0 was faster than at pH 7.0 (58% versus 10% m-THPC released within 48 h, respectively). The in vitro photodynamic therapy efficiency was tested with the HT-29 cell line. m-THPC loaded PEGMA-co-DPA nanoparticles exhibited obvious phototoxicity in HT-29 colon cancer cells after light irradiation. The results indicate that these pH sensitive nanoparticles are potential carriers for tumor targeting and photodynamic therapy.

2-(Diisopropylamino)ethyl methacrylate's production and use as a monomer in the synthesis of homopolymers and copolymers(1) and in research for the production of polymeric nanoparticles for drug delivery applications(2,3) 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 174(SRC), determined from a structure estimation method(2), indicates that 2-(diisopropylamino)ethyl methacrylate is expected to have moderate mobility in soil(SRC). The pKa of 2-(diisopropylamino)ethyl methacrylate is estimated to be 9.53(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 from moist soil is not expected because the compound exists as a cation and cations do not volatilize. Even though the vapor pressure, its estimated vapor pressure of 0.053 mm Hg(SRC), determined from a fragment constant method(2), is low environmentally at standard temperature and pressure, 2-(diisopropylamino)ethyl methacrylate exists is a liquid; therefore, 2-(diisopropylamino)ethyl methacrylate may volatilize from dry soil(SRC). Based on analogy to the similar 2-(N,N-dimethylamino)ethyl methacrylate(5), 2-(diisopropylamino)ethyl methacrylate may degrade via abiotic hydrolysis in moist alkaline and neutral soils(SRC). Utilizing the Japanese MITI test, 70% of the Theoretical BOD was reached in 4 weeks for the analogous 2-(N,N-diethylamino)ethyl methacrylate(6) indicating that biodegradation of 2-(diisopropylamino)ethyl methacrylate may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 174(SRC), determined from a structure estimation method(2), indicates that 2-(diisopropylamino)ethyl methacrylate is not expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 9.83(3) indicates 2-(diisopropylamino)ethyl methacrylate will exist almost entirely in the cation form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 32(SRC), from an estimated log Kow of 2.79(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). The analogous compound 2-(N,N-dimethylamino)ethyl methacrylate is hydrolyzed at pH 7 and at pH 9 with half-lives of 4.54 days and 3.31 hours, respectively (at 25 °C), whereas it is stable at pH 4(5); 2-(diisopropylamino)ethyl methacrylate is expected to have similar hydrolysis rates(SRC). Utilizing the Japanese MITI test, 70% of the Theoretical BOD was reached in 4 weeks for the analogous 2-(N,N-diethylamino)ethyl methacrylate(6) indicating that biodegradation of 2-(diisopropylamino)ethyl methacrylatemay be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-(diisopropylamino)ethyl methacrylate, which has an estimated vapor pressure of 0.053 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 2-(diisopropylamino)ethyl 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 2.9 hours(SRC), calculated from its rate constant of 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Vapor-phase 2-(diisopropylamino)ethyl 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 2-(diisopropylamino)ethyl methacrylate is estimated to be about 6.5 days(SRC).

The rate constant for the vapor-phase reaction of 2-(diisopropylamino)ethyl methacrylate with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 2-(diisopropylamino)ethyl 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 2-(diisopropylamino)ethyl methacrylate is estimated to be about 6.5 days(SRC) at an atmospheric concentration of 2.5X10+8 nitrate radicals per cu cm(3). 2-(Diisopropylamino)ethyl 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). The analogous compound 2-(N,N-dimethylamino)ethyl methacrylate is hydrolyzed at pH 7 and at pH 9 (25 °C) with half-lives of 4.54 days and 3.31 hours, respectively, whereas it is stable at pH 4(5); 2-(diisopropylamino)ethyl methacrylate is expected to have similar hydrolysis rates(SRC). 2-(N,N-Diethylamino)ethyl methacrylate hydrolyzed in water to form methacrylic acid and 2-diethylaminoethanol(6)

An estimated BCF of 32 was calculated in fish for 2-(diisopropylamino)ethyl methacrylate(SRC), using an estimated log Kow of 2.79(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-(diisopropylamino)ethyl methacrylate can be estimated to be 174(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-(diisopropylamino)ethyl methacrylate is expected to have moderate mobility in soil. The estimated pKa of 2-(diisopropylamino)ethyl methacrylate is 9.53(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).

An estimated pKa of 9.53(1) indicates 2-(diisopropylamino)ethyl methacrylate will exist almost entirely in the cation form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). Even though the vapor pressure, its estimated vapor pressure of 0.053 mm Hg(SRC), determined from a fragment constant method(2), is low environmentally at standard temperature and pressure, 2-(diisopropylamino)ethyl methacrylate exists is a liquid; therefore, 2-(diisopropylamino)ethyl methacrylate may volatilize from dry soil(SRC).

Occupational exposure to 2-(diisopropylamino)ethyl methacrylate may occur through inhalation and dermal contact with this compound at workplaces where 2-(N,N-diethylamino)ethyl methacrylate is produced or used(SRC). Based on analogy to the similar 2-(N,N-dimethylamino)ethyl methacrylate(1), the general population may be exposed to 2-(diisopropylamino)ethyl methacrylate via dermal contact with consumer products containing polymers made with the compound and resulting migration of residual monomer from the polymer matrix(SRC).

Polymersomes have the potential to encapsulate and deliver chemotherapeutic drugs into tumor cells, reducing off-target toxicity that often compromises anticancer treatment. Here, we assess the ability of the pH-sensitive poly 2-(methacryloyloxy)ethyl phosphorylcholine (PMPC)- poly 2-(diisopropylamino)ethyl methacrylate (PDPA) polymersomes to encapsulate chemotherapeutic agents for effective combinational anticancer therapy. Polymersome uptake and ability to deliver encapsulated drugs into healthy normal oral cells and oral head and neck squamous cell carcinoma (HNSCC) cells was measured in two and three-dimensional culture systems. PMPC-PDPA polymersomes were more rapidly internalized by HNSCC cells compared to normal oral cells. Polymersome cellular uptake was found to be mediated by class B scavenger receptors. We also observed that these receptors are more highly expressed by cancer cells compared to normal oral cells, enabling polymersome-mediated targeting. Doxorubicin and paclitaxel were encapsulated into pH-sensitive PMPC-PDPA polymersomes with high efficiencies either in isolation or as a dual-load for both singular and combinational delivery. In monolayer culture, only a short exposure to drug-loaded polymersomes was required to elicit a strong cytotoxic effect. When delivered to three-dimensional tumor models, PMPC-PDPA polymersomes were able to penetrate deep into the center of the spheroid resulting in extensive cell damage when loaded with both singular and dual-loaded chemotherapeutics. PMPC-PDPA polymersomes offer a novel system for the effective delivery of chemotherapeutics for the treatment of HNSCC. Moreover, the preferential internalization of PMPC polymersomes by exploiting elevated scavenger receptor expression on cancer cells opens up the opportunity to target polymersomes to tumors.

/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/

2-Propenoic acid, 2-methyl-, 2-[bis(1-methylethyl)amino]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/

Retention times for acrylates & methacrylates were measured with 2 different columns (C18 corasil & C8 lichrosorb) using reverse-phase high pressure liquid chromatography in order to obtain partition coefficients of acrylates and methacrylates between 1-octanol and water (log P). /Acrylates & 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/