1,2-Dimethoxyethane

HCID 8071CAS 110-71-4

Basic information

Standard SMILES
COCCOC
InChIKey
XTHFKEDIFFGKHM-UHFFFAOYSA-N
Molecular formula
C4H10O2
Average molar mass
90.12 g/mol

Overview

1,2-dimethoxyethane appears as 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.

Names & identifiers

Preferred name
1,2-Dimethoxyethane
IUPAC
1,2-dimethoxyethane
English name
1,2-Dimethoxyethane
Molecular formula
C4H10O2
Molecular weight
90.12

Names & synonyms

1,2-DIMETHOXYETHANE110-71-4MonoglymeEthylene glycol dimethyl etherGlymeDimethyl CellosolveDimethoxyethaneEgdme2,5-DioxahexaneEthane, 1,2-dimethoxy-Glycol dimethyl etherDimethylcellosolve
Show more names
DMEGDME1,2-dimethoxy-ethan
Hisolve MMMEthylene dimethyl etherAnsul ether 121DME (glycol ether)Monoethylene glycol dimethyl etherDTXSID0025286alpha,beta-DimethoxyethaneGXS24JF5IW

Database identifiers

CAS
110-71-4、24991-55-7
PubChem CID
8071
DTXSID
DTXSID0025286
ChEMBL
CHEMBL1232411
ChEBI
CHEBI:42263
UNII
GXS24JF5IW
EC Number
203-794-9、607-475-9
Nikkaji
J5.099G

Properties

Computed structural properties

XLogP
-0.2
Topological polar surface area
18.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 3rd degree
DrugsPharmaceuticals -> Listed in ZINC15
SolventsSolvents -> Glycol Ethers (Glymes)
pH8.2
SpringerMaterials PropertiesSchoenflies notation
LogP · 3 items

Log Kow = -0.21

-0.21

-0.21

Physicochemical properties

Melting point
-69 °C · -69 °C
Boiling point
85 °C · 85 °C(lit.)
Density
0.867 g/mL · 0.867 g/mL at 25 °C(lit.)
vapor density
3.1 · 3.1 (20 °C, vs air)
vapor pressure
48 mm · 48 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.379(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H225: 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.

Danger

H225 (99.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]

Hazard information

Regulatory Information · 6 items

Chemical: Ethane, 1,2-dimethoxy-

Hazard Traits - Reproductive Toxicity

Ethane, 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/14829

Substance: 1, 2-dimethoxyethane; ethylene glycol dimethyl ether (EGDME)

Other Safety InformationIMAP assessments - Ethane, 1,2-dimethoxy-: Environment tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 items

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 · 2 items

DANGEROUS, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS

FLAMMABLE, DANGEROUS FIRE RISK

Health Hazards · 2 items

If ingested causes nausea, vomiting, cramps, weakness, coma. (USCG, 1999)

· Inhalation or contact with material may irritate or burn skin and eyes.

Safety & protection

Fire Fighting · 2 items

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 · 4 items

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 · 2 items

· 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 · 2 items

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 StorageCool. Fireproof. Separated from strong oxidants.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

Toxicology

Environmental Fate · 3 items

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 EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by ingestion, by inhalation and through the skin.
Signs and Symptoms · 3 items

MAY BE ABSORBED!

Redness.

Nausea.

Soil Adsorption/Mobility · 1 item

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 · 2 items

...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.

Safety data

F
3-10-23
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
KI1451000
ridadr
UN 2252

Chemistry & industry

Uses & manufacturing

Uses · 4 items

Used as a specialty solvent and reagent; [Merck Index] Used in lithium batteries and industrial coatings; [EPA: Initial Risk-Based Prioritization of HPV Chemicals: Monoglyme]

Battery Manufacturing [Category: Industry]

SOLVENT TO FACILITATE FORMATION OF ALKALI METAL-HYDROCARBON ADDUCTS; IN REFORMATSKY REACTION WITH METHYL GAMMA-BROMOCROTONATE

Process solvent/solubilizer

U.S. Imports · 2 items

(1972) NEGLIGIBLE

(1976) NEGLIGIBLE

U.S. Production · 3 items

2023: 550,000 - <1,000,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.5X10+5 GRAMS

Consumer UsesPropellants, non-motive (blowing agents)
Industry UsesSolvent
Methods of Manufacturing · 3 items

...FROM ETHYLENE GLYCOL MONOMETHYL ETHER, METHYL SULFATE AND METALLIC SODIUM; FROM CHLOROMETHYL METHYL ETHER IN THE PRESENCE OF SODIUM BY WURTZ REACTIONS.

...FROM ETHYLENE GLYCOL MONOMETHYL ETHER, METHYL CHLORIDE AND SODIUM.

Ethylene glycol monomethyl ether + dimethyl sulphate (ether formation)

Applications · 3 items

Description1,2-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].

Uses1,2-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 DescriptionA 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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
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]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

DefinitionChEBI: 1,2-dimethoxyethane is a diether that is the 1,2-dimethyl ether of ethane-1,2-diol. It has a role as a non-polar solvent. It is functionally related to an ethylene glycol.

Related reactions

18,896 records

Linked notes

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