2-프로펜산,2-메틸-,2-(디에틸아미노)에틸에스테르,단독중합체

Diethylaminoethyl Methacrylate

HCID 61012CAS 105-16-8

기본 정보

표준 SMILES
C=C(C)C(=O)OCCN(CC)CC
InChIKey
SJIXRGNQPBQWMK-UHFFFAOYSA-N
분자식
C10H19NO2
평균 분자량
185.26 g/mol
단동위원소 질량
185.14157885

개요

Diethylaminoethylmethacrylate, [liquid] appears as a clear light colored liquid. Insoluble in water and slightly denser than water. May be toxic by ingestion. Contact may severely irritate skin.

이름 및 식별자

우선 이름
Diethylaminoethyl Methacrylate
IUPAC
2-(diethylamino)ethyl 2-methylprop-2-enoate
현지명
2-프로펜산,2-메틸-,2-(디에틸아미노)에틸에스테르,단독중합체
영어명
2-Propenoic acid, 2-methyl-, 2-(diethylamino)ethyl ester, homopolymer
분자식
C10H19NO2
분자량
185.26336

이름 및 동의어

2-(Diethylamino)ethyl methacrylate105-16-8Diethylaminoethyl methacrylateDaktose BN,N-DIETHYLAMINOETHYL METHACRYLATE2-(diethylamino)ethyl 2-methylprop-2-enoate2-Propenoic acid, 2-methyl-, 2-(diethylamino)ethyl ester2-(N,N-Diethylamino)ethyl methacrylateMethacrylic acid, 2-(diethylamino)ethyl ester(2-(Methacryloyloxy)ethyl)diethylamineDTXSID4026713N5SI2E7HOU
이름 더 보기
2-프로펜산,2-메틸-,2-(디에틸아미노)에틸에스테르,단독중합체poly[2-(diethylamino)ethyl methacrylate] macromolecule2-Propenoic acid, 2-methyl-, 2-(diethylamino)ethyl ester, homopolymer
ACRYESTER DEAGEFLEX FM 2PTZNSC-14490DTXCID506713NSC14490GE 710DEAEM CPDEt2NH-ethyl methacrylate

데이터베이스 식별자

CAS
105-16-8、25119-82-8
PubChem CID
61012
DTXSID
DTXSID4026713
ChEMBL
CHEMBL3182085
UNII
N5SI2E7HOU
EC Number
203-275-7
Nikkaji
J107.836D

물성

구조 계산 물성

XLogP
1.9
극성 표면적
29.5 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
7
무거운 원자 수
13

실험 및 물리화학적 성질

PolymersPlastics & Rubber -> (Meth)acrylates
SpringerMaterials PropertiesFusion temperature
Density0.92 g/cu cm at 20 °C
Color/FormClear, colorless liquid
Boiling PointBP: 80 °C at 10 mm Hg
DecompositionWhen heated to decomposition it emits toxic vapors of /nitrogen oxides/.

물리화학적 성질

EPA
2 · 2-Propenoic acid, 2-methyl-, 2-(diethylamino)ethyl ester, homopolymer (25119-82-8)

안전 및 규제

GHS 분류

GHS Classification · 6건

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P317, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Warning

H302 (20%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 4건

Chemical: 2-Propenoic acid, 2-methyl-, 2-(diethylamino)ethyl ester

2-Propenoic acid, 2-methyl-, 2-(diethylamino)ethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 2-(diethylamino)ethyl ester 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)

REACH registered substance: 2-(diethylamino)ethyl methacrylate (EC: 203-275-7)

2-Propenoic acid, 2-methyl-, 2-(diethylamino)ethyl ester: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelFlammable Liquid
Fire HazardsExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Health HazardsExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Hazards Summary · 1건

In gavage studies of rabbits, electrical brain activity was suppressed followed by clonic-tonic spasms; Highly irritating to skin and eyes, based on animal studies; [HSDB] May cause severe skin irritation; [CAMEO] A skin and eye irritant; [eChemPortal: ERMA] A skin and eye irritant; May cause skin sensitization; [eChemPortal: ESIS] An irritant; Can be absorbed through skin; May cause skin sensitization; [MSDSonline] See ACRYLIC RESINS (MONOMERS).

Reactive GroupAmines, Phosphines, and Pyridines

안전 및 보호

Fire FightingExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
First AidExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Fire Fighting Procedures · 2건

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.

Storage Conditions · 3건

Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Moisture sensitive.

To avoid photoinitiation of polymerization, all methacrylates should be stored with minimal exposure to light. /Methacrylates/

The effectiveness of phenolic inhibitors is dependent on the presence of oxygen and the monomers must be stored under air rather than an inert atmosphere. Temperatures must be kept low to minimize formation of peroxides and other products. Moisture may cause rust-initiated polymerization. /Acrylic acid & derivatives/

Cleanup Methods · 1건

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. 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.; 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.

Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 71(SRC), determined from a structure estimation method(2), indicates that 2-(N,N-diethylamino)ethyl methacrylate is expected to have high mobility in soil(SRC). The pKa of 2-(N,N-diethylamino)ethyl methacrylate is estimated to be 8.96(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 2-(N,N-diethylamino)ethyl methacrylate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(2). 2-(N,N-Diethylamino)ethyl methacrylate may volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.11 mm Hg(SRC), determined from a fragment constant method(2). Utilizing the Japanese MITI test, 70% of the Theoretical BOD was reached in 4 weeks(6) suggesting that biodegradation is an important environmental fate process in soil(SRC). Based on the Japanese MITI test(6) and analog to the similar 2-(N,N-dimethylamino)ethyl methacrylate(7), 2-(N,N-diethylamino)ethyl 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 71(SRC), determined from a structure estimation method(2), indicates that 2-(N,N-diethylamino)ethyl 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 2.1X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 9(SRC), from an estimated log Kow of 1.95(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 70% of the Theoretical BOD was reached in 4 weeks(5) suggesting that biodegradation is an important environmental fate process in water(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(6); 2-(N,N-diethylamino)ethyl methacrylate is expected to have very similar hydrolysis rates(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-(N,N-diethylamino)ethyl methacrylate, which has an estimated vapor pressure of 0.11 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-(N,N-diethylamino)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 3.4 hours(SRC), calculated from its rate constant of 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Vapor-phase 2-(N,N-diethylamino)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-(N,N-diethylamino)ethyl methacrylate is estimated to be about 6.5 days(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Toxicity Summary · 1건

IDENTIFICATION AND USE: 2-(N,N-Diethylamino)ethyl methacrylate is a clear, colorless liquid. It is used as a pH-responsive component in the formation of nanocarriers. HUMAN EXPOSURE AND TOXICITY: No human studies available. ANIMAL STUDIES: 2-(N,N-diethylamino)ethyl methacrylate, in acute studies with rabbits, initially suppressed brain electrical activity and then induced clonic-tonic spasms. It was strongly irritating to skin of guinea pigs and conjunctiva of rabbits. Animal studies using rats revealed that some acrylates and methacrylates are embryotoxic. The doses of monomers used in the animal studies, however, were much higher than concentrations likely encountered by workers. This chemical did not induce gene mutations in S. typhimurium and E. coli strains. Toxicity was observed at 5000 ug/plate (TA100, TA1535, TA98, TA1537) without an S9 mix and at 2500 ug/plate (five strains) with an S9 mix. Toxicity was not observed at 5000 ug/plate in WP2 uvrA without an S9 mix. In a chromosome aberration test using Chinese hamster lung cells, structural chromosomal aberrations were induced at 0.30 and 0.60 mg/mL in the presence of an exogenous metabolic activation system.

Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-(N,N-diethylamino)ethyl methacrylate can be estimated to be 71(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-(N,N-diethylamino)ethyl methacrylate is expected to have high mobility in soil. The estimated pKa of 2-(N,N-diethylamino)ethyl methacrylate is 8.96(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).

TSCA Test Submissions · 3건

A combined Repeat Dose and Reproductive/Developmental Toxicity Screen was conducted with 2-(N,N-Diethylamino)ethyl methacrylate (CAS #105-16-8) in groups of Sprague-Dawley CD rats (12/sex/group). In males, the test compound was administered by oral gavage in an olive oil vehicle at doses of 0, 50, 150, or 500 mg/kg/day for 49 days. Females received treatments from 14 days before mating through day 3 of lactation. Terminal sacrifice and necropsy took place the day after final dosing for both males and females. In males receiving 500 mg/kg, the test compound did not appear to effect clinical signs, body weights, food consumption, urinalysis parameters, gross pathology or histology. Males from the high dose group exhibited high values compared to controls for relative and absolute kidney weights as well as for BUN. Males receiving 150 mg/kg had high BUN values and high relative kidney weights when compared to controls. Males in the 50 mg/kg group exhibited no observable effects from the test substance. No effects on clinical signs, body or organ weights, food consumption or histopathology were observed in females from any treatment group. Females in the 500 mg/kg group showed a trend toward a low delivery index and lower numbers of pups born when compared to controls. The test compound was not seen to effect other reproductive parameters in the high dose group, nor were any reproductive effects seen in other treatment groups. There were no effects on any developmental parameters observed in any treatment group. The NOEL for repeat dose toxicity in males was considered to be 50 mg/kg/day, and in females, 500 mg/kg/day. The NOEL for reproductive/developmental effects was considered to be 500 mg/kg/day for males, females, and pups.

2-(N,N-Diethylamino)ethyl methacrylate was tested for mutagenic potential in bacteria. Salmonella typhimurium (strains TA100, TA98, TA1535, and TA1537) and were exposed to 0, 156, 313, 625, 1250, 2500, or 5000 ug of 2-methyl-2-propenoic acid/plate in the presence and absence of S9 metabolic activation. Escherichia coli (strain WP2uvrA) were exposed to 0, 313, 625, 1250, 2500, or 5000 ug of 2-methyl-2-propenoic acid/plate in the presence and absence of S9 metabolic activation. Positive control tests were conducted using 2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide (strains TA100, TA98, and WP2uvrA), sodium azide (strain TA1535), 9-aminoacridine (strain TA1537) with no S9 activation, and 2-aminoanthracene (all strains) with S9 activation. Cytotoxicity was reported for S. typhimurium exposed to 5000 ug/plate without S9 activation and 2500 ug/plate with S9 activation produced toxicity in all bacterial strains examined. No toxicity was seen for E. coli in the 5000 ug/plate group. 2-Methyl-2-propenoic acid did not produce gene mutations in any of the examined strains either with or without S9 activation.

2-(N,N-Diethylamino)ethyl methacrylate was tested for the potential to induce chromosomal aberrations in Chinese hamster lung (CHL) cells, both in the presence and absence of S9 metabolic activation. Plates of CHL cells were exposed for short term (duration of short-term not reported), 24, or 48 hours to 0, 0.075, 0.15, or 0.3 mg/ml without S9 activation mix or for short-term with S9 activation to concentrations of 0, 0.15, 0.30, or 0.60 mg/ml. CHL cells were exposed to Mitomycin C without S9 activation or cyclophosphamide with S9 activation in positive control tests. Concentrations of 0.30 and 0.60 mg/ml produced structural chromosomal aberrations (6.0% and 24.5%, respectively) in the presence of S9 activation mix. Twenty four hour treatment with 0.15 and 0.30 mg/ml and no S9 activation produced 1.75 and 7.25% polyploidy, respectively; 48 hour treatment with 0.30 mg/ml and no S9 activation produced 5.13% polyploidy; and short-term treatment with 0.30 mg/ml produced 7.13% polyploidy, also in the absence of S9 activation.

Artificial Pollution Sources · 1건

2-(N,N-Diethylamino)ethyl methacrylate's production and use as an intermediate for chemical synthesis and as a monomer in the production of a variety of copolymers and homopolymers(1) may result in its release to the environment through various waste streams(SRC).

안전 데이터

tsca
TSCA listed
기존화학 물질
KE-24957

화학 및 산업

약리 정보

Metabolism/Metabolites · 2건

Small quantities of methacrylates may readily be metabolized by saponification into the alcohol and methacrylic acid. The latter may form an acetyl-coenzyme A derivative, which then enters the normal lipid metabolism. /Methacrylates/

Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. They are also likely to be hydrolyzed via carboxylesterases. The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity. /Methacrylates/

용도 및 제조

Uses · 6건

Used as monomer and comonomer for polymers (used in automotive paints and adhesives) and in dental materials and antithrombogenic prosthetics; [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

Laboratory chemicals, Manufacture of substances.

/SRP/: PROPOSED FOR OR USED IN MANUFACTURE OF GRAFT POLYMERS, HAIR SPRAYS, DENTAL MATERIALS, TREATMENT OF SYNTHETIC PELTS, PREPARATION OF COPOLYMERS FOR WASTE WATER PURIFICATION.

MONOMER FOR ACRYLIC POLYMERS USED IN AUTOMOTIVE PAINTS.

COMONOMER FOR POLYMERS USED IN ADHESIVES.

U.S. Production · 3건

2023: 25,000 - <50,000 lb

2-Propenoic acid, 2-methyl-, 2-(diethylamino)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-(diethylamino)ethyl ester. National Production Volume: Withheld.

Industry UsesMonomers
Methods of Manufacturing · 2건

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 DIETHYLAMINOETHANOL WITH EITHER METHYL METHACRYLATE OR METHACRYLIC ACID.

General Manufacturing Information · 3건

All Other Chemical Product and Preparation Manufacturing

2-Propenoic acid, 2-methyl-, 2-(diethylamino)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/

공급사50 곳

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

추가 설명

정의ChEBI: A macromolecule composed of repeating 2-(diethylamino)ethyl isobutyrate units.

관련 반응

7건

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