HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dimethoxyethane
DME · 1,2-DIMETHOXYETHANE · Glyme · Dimethoxyethane · ETHYLENE GLYCOL DIMETHYL ETHER · MONOGLYME · GDME · 1,2-dimethoxy-ethan
Identifiers & Physical Properties
| CAS No. | 110-71-4 |
|---|---|
| Molecular formula | C4H10O2 |
| Average molar mass | 90.12 g/mol |
| SMILES | COCCOC |
| InChIKey | XTHFKEDIFFGKHM-UHFFFAOYSA-N |
| PubChem CID | 8071 |
| ChEMBL | CHEMBL1232411 |
| ChEBI | CHEBI:42263 |
| EC No. | 203-794-9 |
| DTXSID | DTXSID0025286 |
Chemical & Physical Properties
| XLogP | -0.2 |
|---|---|
| Topological polar surface area | 18.5 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 3 |
| Heavy atoms | 6 |
| Formal charge | 0 |
| Complexity | 17.5 |
| Chemical classes | Flammable agents - 3rd degree |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Solvents | Solvents -> Glycol Ethers (Glymes) |
| pH | 8.27 |
| SpringerMaterials Properties | Schoenflies notation |
| LogP (partition coefficient) | Log Kow = -0.21 |
| Odor | SHARP ETHEREAL ODORMild odorwater-wh. liq., sharp ethereal odor |
| Density | 0.868 at 68 °F (USCG, 1999) - Less dense than waterwill float0.86285 @ 20 °C/4 °CRelative density (water = 1): 0.860.86877 @25 °C0.867 g/mL at 25 °C(lit.) |
| Color/Form | WATER-WHITE LIQUIDCOLORLESS LIQUID |
| Solubility | greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)MISCIBLE WITH WATER, ALCOHOLSOL IN HYDROCARBON SOLVENTSSOL IN CHLOROFORM, ETHER, ACETONE, BENZENEwater solubility = 1.00X10+6 mg/l @ 25 °CSolubility in water: miscible1000g/l soluble |
| Flash point | 32 °F (NTP, 1992)-2 °C29 °F(-2 °C) (CLOSED CUP)-2 °C c.c. |
| Boiling point | 185 °F at 760 mmHg (NTP, 1992)82-83 °C @ 760 MM HG85 °C(lit.) |
| Melting point | -69 °C |
| Vapor density | 3.1 (20 °C, vs air) |
| Vapor pressure | 48 mm Hg ( 20 °C) |
| Refractive index | n20/D 1.379(lit.) |
| Storage conditions | Store below +30°C. |
| Physical state | Liquid |
| Color | Clear |
| Explosive limits | 10.4% |
| Specific heat capacity | Cp(liquid): 2.14 J/(g·K), at 25℃ |
| λmax | λ: 220 nm Amax: 1.00λ: 250 nm Amax: 0.20λ: 300 nm Amax: 0.03λ: 350-400 nm Amax: 0.01 |
| Sensitivity | Air Sensitive |
| Merck | 14,3224 |
| BRN | 1209237 |
| Henry's law constant | 1.3×100 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Dielectric constant | 7.2(25℃) |
| Stability | Stable, but explosive peroxides may form on exposure to air. Test for the presence of peroxides before heating. Avoid heat, light, air. Highly flammable. Store under inert gas. |
| Major applications | cleaning productscosmeticsenvironmentalfood and beveragespersonal care |
| InChI | 1S/C4H10O2/c1-5-3-4-6-2/h3-4H2,1-2H3 |
| InChIKey | XTHFKEDIFFGKHM-UHFFFAOYSA-N |
| SMILES | COCCOC |
| LogP (partition coefficient) | -0.21 at 25℃ |
| Surface tension | 24.7mN/m at 293.15K |
| Substances of Very High Concern (SVHC) Candidate List | 1, 2-dimethoxyethaneethylene glycol dimethyl ether (EGDME) (110-71-4) |
| CAS DataBase Reference | 110-71-4(CAS DataBase Reference) |
| EWG's Food Scores | 2 |
| FDA UNII | GXS24JF5IW |
| NIST Chemistry Reference | Ethane, 1,2-dimethoxy-(110-71-4) |
| EPA Substance Registry System | Ethylene glycol dimethyl ether (110-71-4) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS02,GHS07,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H302-H360-H225 |
| GHS precautionary statements | P501-P270-P202-P240-P210-P233-P201-P243-P241-P242-P264-P280-P370+P378-P308+P313-P303+P361+P353-P301+P312+P330-P403+P235-P405 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | F,T |
| Risk statements (R) | 60-61-11-19-20-38 |
| Safety statements (S) | 53-45 |
| UN transport number | UN 2252 |
| Water hazard class (WGK) | 1 |
| RTECS number | KI1451000 |
| F | 3-10-23 |
| Autoignition temperature | 396 °F |
| TSCA inventory status | TSCA listed |
| Hazard class | 3Acute Tox. 4 InhalationFlam. Liq. 2Repr. 1BSkin Irrit. 2 |
| Packing group | II |
| Customs code | 29091900 |
| Storage class | 3 - Flammable liquids |
| Hazardous substances data | 110-71-4(Hazardous Substances Data) |
| REACH registrations | Active |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P317, P318, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.2% (1 of 640) of reports.H225 (99.8%): Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Regulatory information | Chemical: Ethane, 1,2-dimethoxy-Hazard Traits - Reproductive ToxicityEthane, 1,2-dimethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethane, 1,2-dimethoxy- 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)S - indicates a substance that is identified in a final Significant New Use Rule.Status: Active Update: 21-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14829Substance: 1, 2-dimethoxyethaneethylene glycol dimethyl ether (EGDME) |
| Other safety information | IMAP assessments - Ethane, 1,2-dimethoxy-: Environment tier I assessment |
| DOT label | Flammable Liquid |
| Fire hazards | Behavior in Fire: Containers may explode in fires. (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Highly flammable. Vapour/air mixtures are explosive. |
| Fire potential | DANGEROUS, WHEN EXPOSED TO HEAT OR FLAMECAN REACT VIGOROUSLY WITH OXIDIZING MATERIALSFLAMMABLE, DANGEROUS FIRE RISK |
| Health hazards | If ingested causes nausea, vomiting, cramps, weakness, coma. (USCG, 1999)· Inhalation or contact with material may irritate or burn skin and eyes. |
| Hazards summary | TLV Basis is hematologic effect and male reproductive & embryo/fetal damage[ACGIH] 2-Methoxyethanol is a major metaoboliteThe potential health hazard of monoglyme is high based on the results of repeated-dose (blood, thymus, adrenal gland, and testicular degeneration) and developmental (increased fetal death and skeletal effects and decreased fetal body weight) toxicity studies at relatively low doses in animal studies. [EPA: Initial Risk-Based Prioritization of HPV Chemicals: Monoglyme] Reproductive toxin in animal tests[ICSC] Labeled as May impair fertility and May cause harm to the unborn child by EU regulations[Glycol Ethers Online] Inhalation of vapor may cause dizziness or difficulty breathing[HSDB] A severe skin and eye irritant[CAMEO] Reproductive toxin and highly flammable[MSDSonline] See GLYCOL ETHERS. See 2-Methoxyethanol. |
| DOT ID and guide | 2252 127 |
| Reactive group | Ethers |
| EC classification | Symbol: F, TR: 60-61-11-19-20S: 53-45 |
| UN classification | UN Hazard Class: 3UN Pack Group: II |
| Reactivity Alerts | Highly Flammable |
| Fire fighting | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| First aid measures | Fresh air, rest.Remove contaminated clothes. Rinse skin with plenty of water or shower.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. |
| Accidental release measures | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| First aid | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.General First Aid: |
| Safe storage | Cool. Fireproof. Separated from strong oxidants. |
| Exposure control and personal protection | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Fire fighting procedures | EXTINGUISH WITH CHEMICAL, ALCOHOL FOAM, OR CARBON DIOXIDE. COOL EXPOSED CONTAINERS WITH WATER. CONTAINERS MAY EXPLODE IN FIRE.If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources. |
| Nonfire spill response | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| 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. |
| Spillage disposal | Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. |
| Preventive Measures | If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing. |
| Isolation and Evacuation | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:Immediate precautionary measure |
| Environmental fate | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 18(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that 1,2-dimethoxyethane will have very high mobility in soil(SRC). Limited data, based on pure culture studies(4), suggest that this compound may be resistant to biodegradation(SRC). Volatilization of 1,2-dimethoxyethane may be important from dry soil surfaces(SRC) based on a measured vapor pressure of 48 mm Hg(5), but not from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.1X10-6 atm-cu m/mole(6,SRC).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 18(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that 1,2-dimethoxyethane should not adsorb to suspended solids and sediment(SRC) in the water. Limited data, from pure culture studies(4), suggest that this compound may be resistant to biodegradation(SRC). 1,2-Dimethoxyethane may volatilize slowly from water surfaces based on an estimated Henry's Law constant of 1.1X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Estimated half-lives for a model river and model lake are 33 and 240 days, respectively(3,SRC). According to a recommended classification scheme(6), an estimated BCF value of 0.4(3,SRC), from a measured log Kow(2), suggests that bioconcentration of 1,2-dimethoxyethane will be low in aquatic organisms(SRC).ATMOSPHERIC FATE: According to a suggested classification scheme(1), a measured vapor pressure of 48 mm Hg at 20 °C(2) indicates that 1,2-dimethoxyethane will mainly exist in the vapor phase in the ambient atmosphere. Vapor-phase 1,2-dimethoxyethane 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 about 25 hours(3,SRC). |
| Adverse effects | Neurotoxin - Acute solvent syndrome |
| Exposure routes | The substance can be absorbed into the body by ingestion, by inhalation and through the skin. |
| Signs and Symptoms | MAY BE ABSORBED!Redness.Nausea. |
| Soil Adsorption/Mobility | The Koc of 1,2-dimethoxyethane is estimated as approximately 18(SRC), using a measured log Kow of -0.21(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 1,2-dimethoxyethane has very high mobility in soil(SRC). |
| Human Toxicity Excerpts | ...TOXICITY OF ETHYLENE GLYCOL DIMETHYL ETHER MAY BE CONSIDERED TO BE LOW FROM LIMITED REPEATED SHORT EXPOSURES. CARE SHOULD BE EXERCISED, HOWEVER, TO AVOID PROLONGED OR REPEATED INHALATION OF HIGH CONCN OF THE VAPOR.IF /VAPOR/ INHALED, WILL CAUSE DIZZINESS OR DIFFICULT BREATHING. LIQUID IS NOT IRRITATING TO SKIN. IF SWALLOWED, WILL CAUSE NAUSEA, VOMITING OR LOSS OF CONSCIOUSNESS. |
| Artificial Pollution Sources | 1,2-Dimethoxyethane's production and use as a solvent and solubilizer(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | Four pure cultures of bacteria, isolated from either soil or activated sludge, were unable to utilize 1,2-dimethoxyethane as a carbon source(1). |
| Environmental Bioconcentration | An estimated BCF value of 0.4 was calculated for 1,2-dimethoxyethane(SRC), using a measured log Kow of -0.21(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will be low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 1,2-dimethoxyethane is estimated as 1.1X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 1,2-dimethoxyethane will volatilize from slowly moving water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 33 days(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 240 days(2,SRC). Volatilization from dry soil surfaces is expected based on an experimental vapor pressure of 48 mm Hg(3). However, volatilization from moist soil surfaces should not be important based on its estimated Henry's Law constant(1,SRC). |
| Non-Human Toxicity Excerpts | /IN FEMALE RATS/...A SINGLE EXPOSURE TO 8000 PPM CAUSED SIGNIFICANT DECR IN AVOIDANCE RESPONSEHOWEVER...NO EFFECT ON ESCAPE RESPONSE. FURTHER EXPOSURES DECR BOTH RESPONSES, & AFTER 5 DAILY 4 HR EXPOSURES HALF...DIED. ...MASSIVE HEMORRHAGE OF LUNG & GI TRACT. /SEVERAL RATS DIED AFTER 4 HR/4000 PPM/10 EXPOSURES/./IN FEMALE RATS, EXPOSED AT 1000 & 2000 PPM 4 HR/DAY, 5 DAYS/WK/...ALL SURVIVED BUT...SHOWED SIGNIFICANT...AVOIDANCE RESPONSE BUT NO ESCAPE RESPONSE. COMPLETE RECOVERY FROM BEHAVIORAL EFFECTS OCCURRED WITHIN A FEW DAYS AFTER CESSATION OF EXPOSURE. ...THERE WAS A DEFINITE REDUCTION IN GROWTH DEPENDING ON CONCN.1,2-DIMETHOXYETHANE WAS ADMIN TO PREGNANT MICE ON THE 7TH, 8TH, 9TH, & 10TH DAYS OF PREGNANCY. 490 MG/KG WAS ADMIN TO 28 MICE (GROUP A), 350 MG/KG TO 23 MICE (GROUP B) & 250 MG/KG TO 23 MICE (GROUP C). GROUP FETAL MORTALITY RATES: 20% (A), 13.1% (B), & 12.6% (C).ADMIN ON 7TH, 8TH, 9TH & 10TH DAYS OF PREGNANCY: 490 MG/KG/28 MICE (GROUP A), 350 MG/KG/23 MICE (B) & 250 MG/KG/23 MICE (C). SURFACE DEFORMITY RATES: 19.2% (A), 5.1% (B) & 0.3% (C). EXTERNAL BRAIN, PALPEBRAL PATENCY, CAUDAL DEFECT, PERITONEAL HERNIA, & CLEFT PALATE NOTED.ADMIN ON 7TH, 8TH, 9TH, & 10TH DAYS OF PREGNANCY: 490 MG/KG/28 MICE (GROUP A), 350 MG/KG/23 MICE (GROUP B), & 250 MG/KG/23 MICE (GROUP C). FETAL CERVICAL VERTEBRAE ABNORMALITIES, SPINAL FUSION, & COSTAL FUSION DEFORMITY RATES INCREASED WITH INCREASING DOSAGE. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of 1,2-dimethoxyethane with photochemically produced hydroxyl radicals has been estimated as 1.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 25 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). |
| F | 3-10-23 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| RTECS number | KI1451000 |
| UN transport number | UN 2252 |
| Customs code | 29091900 |
| Risk statements (R) | 60-61-11-19-20-38 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS07,GHS08 |
| Hazard symbols | F,T |
| Safety statements (S) | 53-45 |
| Hazard class | 3Acute Tox. 4 InhalationFlam. Liq. 2Repr. 1BSkin Irrit. 2 |
| Storage class | 3 - Flammable liquids |
| Packing group | II |
| GHS hazard statements | H302-H360-H225 |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| Autoignition temperature | 396 °F |
| GHS precautionary statements | P501-P270-P202-P240-P210-P233-P201-P243-P241-P242-P264-P280-P370+P378-P308+P313-P303+P361+P353-P301+P312+P330-P403+P235-P405 |
| Hazardous substances data | 110-71-4(Hazardous Substances Data) |
Applications & Uses
Description
1,2-Dimethoxyethane (DME) is a liquid ether used as an aprotic solvent. It is also known as glyme, monoglyme, dimethyl glycol, ethylene glycol, dimethyl ether, dimethyl cellosolve, and DME. It has the special ability to form chelates thanks to the high flexibility of its chains. Moreover, DME is the molecular model system for the poly(oxyethylene) chain. It is commonly used as a solvent in batteries and in organometallic reaction chemistry since it has higher boiling than diethyl ether and THF[1].
Uses
1,2-Dimethoxyethane is widely used as a solvent for electrolyte of lithium batteries, polysilicones, oligo- and polysaccharides. It plays an important role in Grignard reactions, Suzuki reactions and Stille couplings in organometallic chemistry and in pharmaceutical synthesis. It is a higher boiling point solvent and is used as an alternative to diethyl ether and tetrahydrofuran. It is used for the etching of synthetic polymers like polytetrafluoroethylene and other fluoropolymers with alkali metal dispersions.
General Description
A liquid with a sharp odor. Less dense than water. Flash point 34°F. Mildly toxic by ingestion and inhalation. Severely irritates skin and eyes. Vapors heavier than air. Used to make other chemicals.