Identification and Related Records
- 【Name】
- 2-Hydroxyethyl methacrylate
- 【Registry number】
- 868-77-9 (CAS DataBase Reference)
- 【Synonyms】
-
Glycol methacrylate
2-Hydroxyethyl methycrylate
Ethylene glycol monomethacrylate
Methacrylic acid 2-hydroxyethyl ester
2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester
beta-Hydroxyethyl Methacrylate
BISOMER HEMA
Ethylene glycol methacrylate
GMA
heme-a
Mhoromer
S-(2-HYDROXYETHYL)MERCAPTURIC ACID
N-ACETYL-S-(2-HYDROXYETHYL)-L-CYSTEINE
S-(2-Hydroxyethyl)mercapturic Acid, HEMA
R-(2-Hydroxyethyl)mercapturic Acid, HEMA
HEMA
- 【EINECS(EC#)】
- 212-782-2
- 【Molecular Formula】
- C6H10O3 (Products with the same molecular formula)
- 【Molecular Weight】
- 130.14
- 【Inchi】
- InChI=1/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3
- 【InChIKey】
- WOBHKFSMXKNTIM-UHFFFAOYSA-N
- 【Canonical SMILES】
- CC(=C)C(=O)OCCO
868-77-9.mol
Chemical and Physical Properties
- 【Appearance】
- colourless liquid
- 【Density】
- 1.073
- 【Melting Point】
- -12℃
- 【Boiling Point】
- 205-208℃
- 【Refractive Index】
- 1.451-1.453
- 【Flash Point】
- 101℃
- 【Water】
- soluble
- 【Solubilities】
- soluble
- 【Color/Form】
- Clear mobile liquid
- 【Stability】
- Unstable - may polymerize in the absence of stabilizer. May be stabilized with, or contain small amounts of, diethylene glycol monomethacrylate, di(ethylene glycol)dimethacrylate, methacrylic acid. Incompatible with strong oxidizing agents, free radical initiators, peroxides, steel. Closed containers may explode if heated due to runaway polymer
- 【HS Code】
- 29161490
- 【Storage temp】
- 2-8°C
- 【Spectral properties】
- Index of refraction: 1.4515 @ 20 DEG C/D
IR: 2:345I (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
NMR: 3:50D (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)
MASS: 4071 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
- 【Computed Properties】
- Molecular Weight:130.1418 [g/mol]
Molecular Formula:C6H10O3
XLogP3:0.5
H-Bond Donor:1
H-Bond Acceptor:3
Rotatable Bond Count:4
Exact Mass:130.062994
MonoIsotopic Mass:130.062994
Topological Polar Surface Area:46.5
Heavy Atom Count:9
Formal Charge:0
Complexity:118
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Effective Rotor Count:4
Conformer Sampling RMSD:0.6
CID Conformer Count:32
Safety and Handling
- 【Hazard Codes】
- Xi:Irritant;
- 【Risk Statements】
- R36/38;R43
- 【Safety Statements 】
- S26;S28
- 【Sensitive】
- Air Sensitive
- 【Skin, Eye, and Respiratory Irritations】
- Irritating to eyes and skin.
- 【Transport】
- 无资料
- 【Fire Fighting Procedures】
- 30% GRADE (WITH XYLENE) IS FLAMMABLE; MODERATE FIRE RISK.
- 【Fire Potential】
- 30% GRADE (WITH XYLENE) IS FLAMMABLE; MODERATE FIRE RISK.
- 【Formulations/Preparations】
- The 30% solution is made with xylene. Grades: 30%; 96%.
An inhibitor is usually added to solutions to prolong shelf life.
Commercial products contain hydroquinone methyl ether or similar polymerization inhibitors.
- 【Exposure Standards and Regulations】
- Homopolymers and copolymers of 2-Hydroxyethyl methacrylate is an indirect food additive for use only as a component of adhesives.
- 【Other Preventative Measures】
- ... 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: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
- 【Protective Equipment and Clothing】
- 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/
HYDROXYETHYLMETHACRYLATE WAS DEMONSTRATED TO PASS THROUGH VINYL GLOVES. [MATHIAS C GT ET AL; BR J DERMATOL 100 (4): 447-50 (1979)] PubMed Abstract
- 【Specification】
-
The Ethylene glycol methacrylate, with its CAS registry number 868-77-9, has the IUPAC name of 2-hydroxyethyl 2-methylprop-2-enoate. For being a kind of colourless liquid, this is soluble in water and is sensitive to air. When comes to its production, it could be prepared by the reaction of ethylene oxide and methacrylic acid.
The characteristics of Ethylene glycol methacrylate are as follows: (1)ACD/LogP: 0.43; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.427; (4)ACD/LogD (pH 7.4): 0.427; (5)ACD/BCF (pH 5.5): 1.244; (6)ACD/BCF (pH 7.4): 1.244; (7)ACD/KOC (pH 5.5): 40.696; (8)ACD/KOC (pH 7.4): 40.696; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 46.53; (13)Index of Refraction: 1.443; (14)Molar Refractivity: 32.724 cm3; (15)Molar Volume: 123.459 cm3; (16)Polarizability: 12.973×10-24 cm3; (17)Surface Tension: 33.723 dyne/cm; (18)Density: 1.054 g/cm3; (19)Flash Point: 97.222 °C; (20)Enthalpy of Vaporization: 49.49 kJ/mol; (21)Boiling Point: 189.031 °C at 760 mmHg; (22)Vapour Pressure: 0.159 mmHg at 25°C; (23)Exact Mass: 130.062994; (24)MonoIsotopic Mass: 130.062994; (25)Topological Polar Surface Area: 46.5; (26)Heavy Atom Count: 9; (27)Complexity: 118.
Production method of this chemical: oxirane could react with 2-methyl-acrylic acid to produce Ethylene glycol methacrylate. This reaction could happen in the presence of the reagent of Py, Cu(OAc)2.
Use of this chemical: Ethylene glycol methacrylate could react with isobutyryl chloride to produce 1-isobutyryloxy-2-methacryloyloxy-ethane. This reaction could happen in the presence of the reagent of pyridine.
When you are dealing with this chemical, you should be very careful. This is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. And it may cause sensitisation by skin contact. Therefore, you should wear suitable protective clothing and gloves. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice, and after contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer).
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(=C)C(=O)OCCO
(2)InChI: InChI=1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3
(3)InChIKey: WOBHKFSMXKNTIM-UHFFFAOYSA-NBelow are the toxicity information of this chemical:
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source dog LDLo intravenous 99200nL/kg (99200mL/kg) Journal of Pharmaceutical Sciences. Vol. 63, Pg. 376, 1974.
guinea pig LD50 oral 4680mg/kg (4680mg/kg) BEHAVIORAL: COMA Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 54(9), Pg. 75, 1989. mouse LD50 intraperitoneal 497mg/kg (497mg/kg) Journal of Pharmaceutical Sciences. Vol. 62, Pg. 778, 1973.
mouse LD50 oral 3275mg/kg (3275mg/kg) BEHAVIORAL: COMA Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 54(9), Pg. 75, 1989. rat LD50 intraperitoneal 1250mg/kg (1250mg/kg) Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 36, Pg. 58, 1975. rat LD50 oral 5050mg/kg (5050mg/kg) BEHAVIORAL: COMA Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 54(9), Pg. 75, 1989.
- 【Octanol/Water Partition Coefficient】
- log Kow= 0.47
- 【Report】
-
The Ethylene glycol methacrylate, with its CAS registry number 868-77-9, has the IUPAC name of 2-hydroxyethyl 2-methylprop-2-enoate. For being a kind of colourless liquid, this is soluble in water and is sensitive to air. When comes to its production, it could be prepared by the reaction of ethylene oxide and methacrylic acid.
The characteristics of Ethylene glycol methacrylate are as follows: (1)ACD/LogP: 0.43; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.427; (4)ACD/LogD (pH 7.4): 0.427; (5)ACD/BCF (pH 5.5): 1.244; (6)ACD/BCF (pH 7.4): 1.244; (7)ACD/KOC (pH 5.5): 40.696; (8)ACD/KOC (pH 7.4): 40.696; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 46.53; (13)Index of Refraction: 1.443; (14)Molar Refractivity: 32.724 cm3; (15)Molar Volume: 123.459 cm3; (16)Polarizability: 12.973×10-24 cm3; (17)Surface Tension: 33.723 dyne/cm; (18)Density: 1.054 g/cm3; (19)Flash Point: 97.222 °C; (20)Enthalpy of Vaporization: 49.49 kJ/mol; (21)Boiling Point: 189.031 °C at 760 mmHg; (22)Vapour Pressure: 0.159 mmHg at 25°C; (23)Exact Mass: 130.062994; (24)MonoIsotopic Mass: 130.062994; (25)Topological Polar Surface Area: 46.5; (26)Heavy Atom Count: 9; (27)Complexity: 118.
Production method of this chemical: oxirane could react with 2-methyl-acrylic acid to produce Ethylene glycol methacrylate. This reaction could happen in the presence of the reagent of Py, Cu(OAc)2.
Use of this chemical: Ethylene glycol methacrylate could react with isobutyryl chloride to produce 1-isobutyryloxy-2-methacryloyloxy-ethane. This reaction could happen in the presence of the reagent of pyridine.
When you are dealing with this chemical, you should be very careful. This is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. And it may cause sensitisation by skin contact. Therefore, you should wear suitable protective clothing and gloves. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice, and after contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer).
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(=C)C(=O)OCCO
(2)InChI: InChI=1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3
(3)InChIKey: WOBHKFSMXKNTIM-UHFFFAOYSA-NBelow are the toxicity information of this chemical:
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source dog LDLo intravenous 99200nL/kg (99200mL/kg) Journal of Pharmaceutical Sciences. Vol. 63, Pg. 376, 1974.
guinea pig LD50 oral 4680mg/kg (4680mg/kg) BEHAVIORAL: COMA Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 54(9), Pg. 75, 1989. mouse LD50 intraperitoneal 497mg/kg (497mg/kg) Journal of Pharmaceutical Sciences. Vol. 62, Pg. 778, 1973.
mouse LD50 oral 3275mg/kg (3275mg/kg) BEHAVIORAL: COMA Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 54(9), Pg. 75, 1989. rat LD50 intraperitoneal 1250mg/kg (1250mg/kg) Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 36, Pg. 58, 1975. rat LD50 oral 5050mg/kg (5050mg/kg) BEHAVIORAL: COMA Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 54(9), Pg. 75, 1989.
- 【Disposal Methods】
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Use and Manufacturing
- 【Use and Manufacturing】
- Methods of 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/
REACTION OF METHACRYLIC ACID WITH ETHYLENE OXIDE; TRANSESTERIFICATION OR ESTERIFICATION OF ETHYLENE GLYCOL WITH EITHER METHYL METHACRYLATE OR METHACRYLIC ACID.
Hydroxyalkyl methacrylates are prepared by the addition of methacrylic acid to the epoxide ring of alkylene oxides to form hydroxyalkyl methacrylates, ie, beta-hydroxyethyl and hydroxypropyl methacrylate. Oxides other than ethylene oxide give isomeric products; commercial hydroxypropyl methacrylate has about a 2-to-1 ratio of 2-hydroxypropyl methacrylate to 1-methyl-2-hydroxyethyl methacrylate. Effective catalysts include tertiary amines, anion-exchange resins, ferric chloride, and lithium methacrylate.U.S. Imports
(1983) 1.36X10+9 g /Acrylates & Acrylic Acid/U.S. Production
(1982) 3.63-5.45X10+9 G (EST)
- 【Usage】
- Acrylic resins, binder for nonwoven fabrics, enamels.
Environmental Fate and Exposure Potential
- 【Environmental Fate/Exposure Summary】
- The rate constant for the vapor-phase reaction of 2-hydroxyethyl methacrylate with photochemically-produced hydroxyl radicals has been estimated as 2.4X10-11 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 16 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 2-hydroxyethyl methacrylate with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 7X10+11 molecules/cu cm(1). Hydrolysis of 2-hydroxyethyl methacrylate may be a significant process under alkaline conditions based upon a hydrolytic half-life of 4 hours at pH 11 for the structurally similar butyl acrylate(2); half-lives for butyl acrylate at pH 7, 8, and 9 were 4 years, 150 days, and 15 days(SRC), respectively, based upon a hydrolytic rate constant of 0.053 L/mole-sec(4). 2-Hydroxyethyl methacrylate is not expected to directly photolyze in sunlight(SRC) based upon the lack of absorption of light at wavelengths >290 nm by the structurally similar ethyl methacrylate(3).
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