Triethylene glycol monomethyl ether
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Triethylene glycol monomethyl ether
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CAS No:
112-35-6
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Formula:
C7H16O4
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Chemical Name:
Triethylene glycol monomethyl ether
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Synonyms:
Ethanol,2-[2-(2-methoxyethoxy)ethoxy]-;2-[2-(2-Methoxyethoxy)ethoxy]ethanol;Dowanol TMAT;Triethylene glycol monomethyl ether;Triglycol monomethyl ether;Methyltrioxitol;3,6,9-Trioxa-1-decanol;3,6,9-Trioxadecanol;Methyltriglycol;NSC 97395;Bikanol M 3;Hymol TM;Monomethoxytriethylene glycol;MTG;2-[2-(2-Methoxyethoxy)ethoxy]ethan-1-ol;2-(2-(2-Methoxyethoxy)ethoxy)ethan-1-ol
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CAS No:
Description
m-PEG3-alcohol is a PEG-based PROTAC linker can be used in the synthesis of PROTACs.
Triethylene glycol methyl ether is a colorless odorless liquid. (USCG, 1999)|Liquid|COLOURLESS-TO-YELLOW LIQUID.
Triethylene glycol methyl ether is a colorless odorless liquid. (USCG, 1999)|Triethylene glycol monomethyl ether is a hydroxypolyether that is the monomethyl ether derivative of triethylene glycol. Metabolite observed in cancer metabolism. It has a role as a human metabolite. It derives from a triethylene glycol.
Triethylene glycol monomethyl ether Basic Attributes
164.2
164.20
203-962-1
DN0P4Q4I16
1291
97395
DTXSID5026912
Colorless liquid
2909499000
Characteristics
47.9
-1.46 (calculated)
Triethylene glycol methyl ether is a colorless odorless liquid. (USCG, 1999)
1.0494 g/cm3
-44 °C
249 °C
>230 °F
1.427
Solubility in water: miscible
Store below +30°C.
<0.01 mm Hg ( 20 °C)
5.66 (vs air)
Henry's Law constant = 3.50X10-14 atm-cu m/mol at 25 °C (est)
Viscosity = 280 cSt (-40 °C)|Hydroxyl radical reaction rate constant = 4.00X10-11 cu cm/molec-sec at 25 °C (est)
Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid.
Alcohols and Polyols
Peroxidizable Compound
Ethers, such as TRIETHYLENE GLYCOL METHYL ETHER, can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.
210 °C
Safety Information
NONH for all modes of transport
1
24/25-22
KL6390000
Separated from strong oxidants, strong bases and strong acids.
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
H315
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Glycol ethers, glycols, ketones, and alcohols undergo violent decomposition in contact with 68-72% perchloric acid
Combustible.
|Warning|H315 (97.44%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 303 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Not Classified
Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing. Fire Extinguishing Agents: Dry chemical, carbon dioxide, or alcohol foam. (USCG, 1999)|Use powder, foam, carbon dioxide.
Chemical safety goggles and adequate protective clothing. (USCG, 1999)
Combustible
... Low oral toxicity and is not injurious to the eyes and skin.
Collect leaking liquid in covered containers. Then store and dispose of according to local regulations. Wash away spilled liquid with plenty of water.
Separated from strong oxidants, strong bases and strong acids.
A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
NO open flames.
PREVENT GENERATION OF MISTS!
Use ventilation.
Protective gloves.
Wear safety spectacles.
| 1 - Materials that, under emergency conditions, can cause significant irritation.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.
Triethylene glycol monomethyl ether was listed as a contaminant found in advanced treatment water in Lake Tahoe, CA(1).
Triethylene glycol monomethyl ether was identified in a sample of fine organometallic automobile brake lining wear particles at a concentration of 248.1 ug/g of particle sampled(1).
Toxicity
LD50 Rat oral 11.8 g/kg|LD50 Rat iv 8.1 g/kg|LD50 Rat ip 7.4 g/kg|LD50 Rat (male Wistar) oral 11300 mg/kg|LD50 Rabbit dermal 7100 mg/kg
Triethylene glycol monomethyl ether's production and use as a plasticizer intermediate(1), coupling solvent, brake/hydraulic fluid blending component, wetting agent, and solvent 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 10(SRC), determined from a structure estimation method(2), indicates that triethylene glycol monomethyl ether is expected to have very high mobility in soil(SRC). Volatilization of triethylene glycol monomethyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Triethylene glycol monomethyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-3 mm Hg(SRC), determined from a fragment constant method(4). Triethylene glycol monomethyl ether has percent theoretical BOD values of 14 and 23 at 10 and 20 days, respectively(5), which suggest that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that triethylene glycol monomethyl ether 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 3.5X10-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -1.46(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Triethylene glycol monomethyl ether has percent theoretical BOD values of 14 and 23 at 10 and 20 days, respectively(8), which suggest that biodegradation is not 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), triethylene glycol monomethyl ether, which has an estimated vapor pressure of 3.5X10-3 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 triethylene glycol monomethyl ether 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 9.6 hours(SRC), calculated from its rate constant of 4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).
The rate constant for the vapor-phase reaction of triethylene glycol monomethyl ether with photochemically-produced hydroxyl radicals has been estimated as 4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9.6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Triethylene glycol monoethyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2).
An estimated BCF of 3 was calculated in fish for triethylene glycol monomethyl ether(SRC), using an estimated log Kow of -1.46(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 triethylene glycol monomethyl ether can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that triethylene glycol monomethyl ether is expected to have very high mobility in soil(SRC).
The Henry's Law constant for triethylene glycol monomethyl ether is estimated as 3.5X10-14 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that triethylene glycol monomethyl ether is expected to be essentially nonvolatile from water surfaces(2). Triethylene glycol monomethyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-3 mm Hg(SRC), determined from a fragment constant method(3).
DRINKING WATER: Triethylene glycol monomethyl ether was listed as a contaminant found in drinking water in Philadelphia, PA(1).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 18,956 workers (9842 of these are female) are potentially exposed to triethylene glycol monomethyl ether in the US(1). Occupational exposure to triethylene glycol monomethyl ether may occur through inhalation and dermal contact with this compound at workplaces where triethylene glycol monomethyl ether is produced or used(SRC). Monitoring data indicate that the general population may be exposed to triethylene glycol monomethyl ether via ingestion of contaminated drinking water(SRC).
Drug Information
It is slowly absorbed through skin. Excessive exposure involving large areas of skin for extended periods of time would be required before serious effects would be expected.|The penetration of triethylene glycol monomethyl ether (TGME) through human skin was studied in vitro using the epidermis from human abdominal skin. An area of 2.54 sq cm was exposed in a glass diffusion apparatus for treatment. The diffusion rate for TGME is 34 ug/sq cm/hr.
The main metabolic pathway for metabolism of TGME and TGEE (and presumably the category members) is oxidation via alcohol dehydrogenase that leads to the formation of an alkoxy acid. A second important route of metabolism is oxidation by P-450 mixed function oxidases (O-dealkylation) that lead to the formation of triethylene glycol (TEG). TEG may be oxidized to a carboxylic acid. The principal metabolite of TGME is believed to be 2-[2-(2-methoxyethoxy)ethoxy] acetic acid.
No appreciable hazard in ordinary handling or use. (USCG, 1999)
Wash affected parts with water. (USCG, 1999)
Fresh air, rest.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
Rinse with plenty of water (remove contact lenses if easily possible).
/EPIDEMIOLOGY STUDIES/ Ethylene glycol ethers (EGEs) including diglyme are used in the manufacture of semiconductors. Epidemiological studies of semiconductor populations evaluated potential adverse reproductive outcomes. ... In each of these studies, workers were exposed to mixtures including diglyme but not to diglyme alone. ... Exposure to EGEs was determined using questionnaires from subjects about the work performed and an assessment of the work environment by industrial hygienists, but no measurements of personal or area exposures were made. Workers in the fabrication area were considered exposed to EGEs. For the retrospective study, information on pregnancy outcomes and potential confounders (age, smoking, ethnicity, education, income, year of pregnancy, and stress) was obtained through a comprehensive interviewer-administered interview of female employees. The prospective study of early fetal loss and fecundity (probability of conception per menstrual cycle) was conducted in a subset of female employees from five plants. Daily diaries and measurements of daily urinary human chorionic gonadotrophin (hCG) levels for 6 months were collected in addition to the comprehensive interview. Of the 891 medically verified pregnancies identified for the retrospective study, 774 (86.9%) were live births, 113 (12.7%) were spontaneous abortions, and 4 (0.4%) were stillbirths. The overall unadjusted relative risk (RR) for spontaneous abortions was 1.45 (95% confidence interval [CI] = 1.02-2.05) and changed little after adjusting for confounders (adjusted RR =1.43; 95% CI = 0.95-2.09). When stratified by work group, the risk of spontaneous abortion was statistically significantly increased for female workers in the photolithography group (RR = 1.67; 95% CI = 1.04-2.55) and in the etching group (RR = 2.08; 95% CI = 1.27-3.19). For women working with higher levels of EGE only in masking, the risk for spontaneous abortion was increased 3-fold (RR = 3.38; 95% CI = 1.61-5.73). In the prospective study, no statistically significant differences were detected in the overall rate of spontaneous abortions between fabrication and non-fabrication workers or when pregnancy outcomes were examined by work group. However, the ability to conceive was lower among female workers exposed to EGEs (fertility rate [FR] = 0.37; 95% CI = 0.11-1.19). /Ethylene glycol ethers/|/BIOMONITORING/ In the present study, floor lacquerers' (n = 22) inhalation and total exposure to 2-(2-alkoxy)ethoxyethanols was measured. The measurements of inhalation exposure were done with charcoal tubes, and total exposure was biomonitored by urinalysis of 2-(2-alkoxyethoxy)acetic acids. The 8 hr inhalation exposures of floor lacquerers to 2-(2-methoxyethoxy)ethanol (DEGME), 2-(2-ethoxyethoxy)ethanol (DEGEE) and 2-(2-butoxyethoxy)ethanol (DEGBE) were in average 0.23 +/- 0.07 ppm (average +/-S.D., n = 3), 0.08 +/- 0.07 ppm (n = 16), and 0.05 +/- 0.03 ppm (n = 16), respectively. The excretions of 2-(2-methoxyethoxy)acetic acid (MEAA), 2-(2-ethoxyethoxy)acetic acid (EEAA) and 2-(2-butoxyethoxy)acetic acid (BEAA) were in average 4.9 +/- 4.3 mmol/mol creatinine, 9.3 +/- 8.0 mmol/mol creatinine and 9.2 +/- 7.4 mmol/mol creatinine, respectively. A linear relationship was found between the urinary 2-(2-alkoxyethoxy)acetic acid concentrations and the preceding 8-hr occupational exposure to 2-(2-alkoxyethoxy)ethanol.
Triethylene glycol monomethyl ether Use and Manufacturing
Ethylene glycol monoethers are commercially manufactured by reaction of an alcohol with ethylene oxide. /Ethylene Glycol Monoethers/|Ethylene glycol monoethers are usually produced by reaction of ethylene oxide with the appropriate alcohol. A mixture of homologues is obtained ... The glycol monoethers can be converted to diethers by alkylation with common alkylating agents, such as dimethyl sulfate or alkyl halides ( Williamson synthesis). Glycol dimethyl ethers are formed by treatment of dimethyl ether with ethylene oxide. /Ethers/
Used as brake fluid and chemical raw materials
Functional fluids (closed systems)
Automotive care products
10,000,000 - 50,000,000 lb|(1972) 1.44X10+10 GRAMS|(1975) 1.77X10+10 GRAMS|(2006) 1,612 million lb annual capacity /Glycol ethers/|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2668]|This chemical is listed as a High Production Volume (HPV) (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).
(ALL TRIETHYLENE GLYCOL MONOETHERS) 95% AS A SOLVENT IN HYDRAULIC BRAKE FLUIDS; 5% AS A SOLVENT IN PROTECTIVE COATINGS, PRINTING INKS, & CHEMICAL SPECIALTIES (1972)
All other basic organic chemical manufacturing|Ethanol, 2-[2-(2-methoxyethoxy)ethoxy]-: ACTIVE
Analyte: triethylene glycol monomethyl ether; matrix: air; procedure: gas chromatography with flame ionization detection|Analyte: triethylene glycol monomethyl ether; matrix: domestic and industrial wastewater; procedure: high resolution gas chromatography with mass spectrometry and high-performance liquid chromatography
Computed Properties
Molecular Weight:164.20
XLogP3:-1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:8
Exact Mass:164.10485899
Monoisotopic Mass:164.10485899
Topological Polar Surface Area:47.9
Heavy Atom Count:11
Complexity:67.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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