ChemicalBook > CAS DataBase List > 1,2-Dimethoxyethane

1,2-Dimethoxyethane

Product Name
1,2-Dimethoxyethane
CAS No.
110-71-4
Chemical Name
1,2-Dimethoxyethane
Synonyms
1,2-DIMETHOXYETHANE;Glyme;Dimethoxyethane;ETHYLENE GLYCOL DIMETHYL ETHER;MONOGLYME;GDME;1,2-dimethoxy-ethan;Egdme;2,5-Dioxahexane;Glycol dimethyl ether
CBNumber
CB9232185
Molecular Formula
C4H10O2
Formula Weight
90.12
MOL File
110-71-4.mol
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1,2-Dimethoxyethane Property

Melting point:
-69 °C
Boiling point:
85 °C(lit.)
Density 
0.867 g/mL at 25 °C(lit.)
vapor density 
3.1 (20 °C, vs air)
vapor pressure 
48 mm Hg ( 20 °C)
refractive index 
n20/D 1.379(lit.)
Flash point:
32 °F
storage temp. 
Store below +30°C.
solubility 
1000g/l soluble
form 
Liquid
color 
Clear
Odor
water-wh. liq., sharp ethereal odor
explosive limit
10.4%
Water Solubility 
Miscible
Sensitive 
Air Sensitive
λmax
λ: 220 nm Amax: 1.00
λ: 250 nm Amax: 0.20
λ: 300 nm Amax: 0.03
λ: 350-400 nm Amax: 0.01
Merck 
14,3224
BRN 
1209237
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.
InChIKey
XTHFKEDIFFGKHM-UHFFFAOYSA-N
LogP
-0.21 at 25℃
CAS DataBase Reference
110-71-4(CAS DataBase Reference)
NIST Chemistry Reference
Ethane, 1,2-dimethoxy-(110-71-4)
EPA Substance Registry System
Ethylene glycol dimethyl ether (110-71-4)
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Safety

Hazard Codes 
F,T
Risk Statements 
60-61-11-19-20-38
Safety Statements 
53-45
RIDADR 
UN 2252 3/PG 2
WGK Germany 
1
RTECS 
KI1451000
F 
3-10-23
Autoignition Temperature
396 °F
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29091900
Hazardous Substances Data
110-71-4(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H315Causes skin irritation

H332Harmful if inhaled

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
E27408
Product name
1,2-Dimethoxyethane
Purity
ReagentPlus?, ≥99%, inhibitor-free
Packaging
18L
Price
$1670
Updated
2024/03/01
Sigma-Aldrich
Product number
8.00856
Product name
Ethylene glycol dimethyl ether
Purity
(stabilised) for synthesis
Packaging
1L
Price
$168
Updated
2024/03/01
Sigma-Aldrich
Product number
8.00856
Product name
Ethylene glycol dimethyl ether
Purity
(stabilised) for synthesis
Packaging
10L
Price
$708
Updated
2024/03/01
Sigma-Aldrich
Product number
72405
Product name
1,2-Dimethoxyethane
Purity
analytical standard
Packaging
5ml
Price
$171
Updated
2024/03/01
Sigma-Aldrich
Product number
259527
Product name
1,2-Dimethoxyethane
Purity
anhydrous, 99.5%, inhibitor-free
Packaging
6x1l
Price
$996
Updated
2024/03/01
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1,2-Dimethoxyethane Chemical Properties,Usage,Production

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].

Chemical Properties

Ethylene glycol dimethyl ether, also called 1,2-Dimethoxyethane, is a colorless liquid with a strong smell similar to ether. It is stable and does not easily react. It can dissolve different resins and cellulose, and can be mixed with water and various organic solvents like alcohols, ketones, and esters in any amount. Its solubility can be changed by diluting it with water or specific solvents.

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.

Definition

ChEBI: 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.

Application

Monoglyme serves as an electrolyte solution component for lithium batteries. It is also frequently utilized as a solvent in organometallic reactions, particularly those involving organolithium compounds. Additionally, it can act as a ligand in certain chemical reactions.

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.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

When the solvent, 1,2-Dimethoxyethane, was poured into a funnel previously used to introduce the lithium aluminum hydride, a fire ignited the funnel, [MCA Case History 1182(1966)].

Hazard

Moderate fire risk.

Health Hazard

If ingested causes nausea, vomiting, cramps, weakness, coma.

Fire Hazard

Behavior in Fire: Containers may explode in fires.

Safety Profile

An experimental teratogen. Other experimental reproductive effects. Readdy forms an explosive peroxide. A very dangerous fire hazard when exposed to heat, flame, or oxidzers. Mixture with lithium tetrahydroaluminate may ignite orexplode if heated. When heated to decomposition it emits acrid smoke and fumes. See also GLYCOL ETHERS.

Synthesis

1,2-Dimethoxyethane is derived from the reaction of ethylene glycol monomethyl ether with sodium metal and methyl chloride. The ethylene glycol monomethyl ether and the metal sodium were refluxed together until the metal sodium was completely reacted, the temperature was lowered to 45° C., and methyl chloride was introduced. After the reaction is completed, fractional distillation is performed to collect fractions at 84-85.5°C to obtain 1,2-Dimethoxyethane.

Purification Methods

Traces of water and acidic materials have been removed from it by refluxing with Na, K or CaH2, decanting and distilling from Na, K, CaH2 or LiAlH4. The reaction has been speeded up by using vigorous high-speed stirring with molten potassium. For virtually complete elimination of water, 1,2-dimethoxyethane has been dried with Na-K alloy until a characteristic blue colour is formed in the solvent at Dry-ice/cellosolve temperatures: the solvent is kept with the alloy until distilled for use [Ward J Am Chem Soc 83 1296 1961]. Alternatively, glyme, refluxed with benzophenone and Na-K, is dry enough if, on distillation, it gives a blue colour of the ketyl immediately on addition to benzophenone and sodium [Ayscough & Wilson J Chem Soc 5412 1963]. It has also been purified by distillation under N2 from sodium benzophenone ketyl (see above). [Beilstein 1 IV 2376.]

References

[1] Weixing Li . “The microwave spectroscopy study of 1,2-dimethoxyethane.” Journal of Molecular Spectroscopy 337 (2017): Pages 3-8.

1,2-Dimethoxyethane Preparation Products And Raw materials

Raw materials

2-Methoxyethanol Sodium hydroxide

Preparation Products

Tetrahydrocurcumin 2-Aminoquinoline 3-AMINOBIPHENYL 5-CHLORO-2'-DEOXYURIDINE TERT-BUTYL 4-(4-FORMYL-1,3-THIAZOL-2-YL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE 2-Bromo-5-hydroxypyridine radical ion(1+) 4-BENZYL-MORPHOLINE-2-CARBOXYLIC ACID 1-METHYL-1H-INDOLE-5-BORONIC ACID 2,2-DIMETHYL PROPANE DIOL-1,3-CYCLIC ESTER EUROPIUM D-3-TRIFLUOROACETYLCAMPHORATE 2-Chloro-5-cyano-3-methylpyridine Quinacridone 4-CHLORO-1,3-DIMETHYLPYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLIC ACID 3-N-Boc-amino-azetidine 4-CHLORO-7-METHYLTHIENO[3,2-D]PYRIMIDINE 3-TRIFLUOROACETYL-D-CAMPHOR TEMAFLOXACIN Azetidine N,N-DIPHENYLQUINACRIDONE Pigment Red 122 4-Thiazolecarboxylic acid 2-CHLORO-5-IODO-3-METHYLPYRIDINE 7-Methylthieno[3,2-d]pyrimidin-4(3H)-one ETHYL 4-METHOXY-3-OXO-BUTANOATE Sarafloxacin 10-UNDECYNOIC ACID 3,4-DICHLORO-N-METHYLANILINE N,N'-Dimethylquinacridone THIOPHENE-2,5-DICARBOXYLIC ACID MONOMETHYL ESTER 4-(Dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran TERT-BUTYL 4-(5-FORMYL-4-METHYL-1,3-THIAZOL-2-YL)PIPERIDINE-1-CARBOXYLATE TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ISOINDOLINE-2-CARBOXYLATE Beraprost 1,1,1-TRICHLOROACETONE 2,3,5,6-Tetrafluorobenzyl alcohol 2-PHENYLMALONAMIDE 5-FORMYL-2-THIOPHENECARBOXYLIC ACID 4'-BROMO-3'-FLUOROACETANILIDE 2,3,5,6-Tetrafluoro-4-methylbenzyl alcohol
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1,2-Dimethoxyethane Suppliers

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View Lastest Price from 1,2-Dimethoxyethane manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
DME 110-71-4
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-19
Anhui lixing chemical co.,ltd
Product
1,2 DIMETHOXYETAHNE 110-71-4
Price
US $0.00-0.00/KG
Min. Order
180KG
Purity
99.5%MIN
Supply Ability
4000tons
Release date
2023-08-03
Anhui lixing chemical co.,ltd
Product
1,2 DIMETHOXYETHANE 110-71-4
Price
US $0.00-0.00/KG
Min. Order
180KG
Purity
99.5%MIN
Supply Ability
4000tons
Release date
2023-09-20

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