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110-71-4

Basic Information
CAS No.: 110-71-4
Name: 1,2-Dimethoxyethane
Article Data: 84
Cas Database
Molecular Structure:
Molecular Structure of 110-71-4 (1,2-Dimethoxyethane)
Formula: C4H10O2
Molecular Weight: 90.1222
Synonyms: DME (glycol ether);Dimethyl Cellosolve;Ethylene dimethyl ether;Ethylene glycol dimethyl ether;Glycol dimethyl ether;Glyme;Hisolve MMM;Monoethylene glycol dimethyl ether;Monoglyme;a,b-Dimethoxyethane;Ethylene glycol dimethy ether;1,2-Ethanediol, dimethyl ether;2,5-Dioxahexane;
EINECS: 203-794-9
Density: 0.839 g/cm3
Melting Point: -69 °C
Boiling Point: 84.5 °C at 760 mmHg
Flash Point: 0 °C
Solubility: Miscible with water
Appearance: water-white Liquid
Hazard Symbols: FlammableF,ToxicT
Risk Codes: 60-61-11-19-20
Safety: 53-45
Transport Information: UN 2252 3/PG 2
PSA: 18.46000
LogP: 0.27920
Synthetic route
74-87-3

methylene chloride

111-77-3

2-(2-methoxyethoxy)ethyl alcohol

110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With sodium hydroxide In water at 60℃;99.8%
115-10-6

Dimethyl ether

109-86-4

2-methoxy-ethanol

110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With MCM-22 In 1,4-dioxane at 50℃; under 750.075 Torr; Pressure; Reagent/catalyst; Temperature; Inert atmosphere;
With hydrogen-type mordenite molecular sieve, Si:Al ratio 4:1 at 200℃; under 60006 Torr; Temperature; Pressure; Reagent/catalyst; Autoclave;
109-86-4

2-methoxy-ethanol

110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With sodium Behandeln des Reaktionsgemisches mit Methylchlorid, zuletzt bei 60grad;
With sulfuric acid
With H-type ZSM-5(SiO2/Al2O3=280) at 180℃; for 11h;
With sulfuric acid
With sodium Behandeln des Reaktionsgemisches mit Dimethylsulfat, zuletzt bei 85-90grad;
67-56-1

methanol

109-86-4

2-methoxy-ethanol

110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With MCM-22 zeolite at 50℃; under 750.075 Torr; Reagent/catalyst; Pressure; Temperature;
109-86-4

2-methoxy-ethanol

A

110-71-4

1,2-dimethoxyethane

B

107-21-1

ethylene glycol

Conditions
ConditionsYield
With H-β molecular sieve catalyst at 70℃; under 3750.38 Torr; Reagent/catalyst; Temperature; Pressure; Inert atmosphere;
67-56-1

methanol

109-86-4

2-methoxy-ethanol

107-21-1

ethylene glycol

110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With NAFION 1100 EW Polymer (H+ form) at 200℃; under 36201.3 - 51716.2 Torr; for 82h;
115-10-6

Dimethyl ether

109-86-4

2-methoxy-ethanol

A

123-91-1

1,4-dioxane

B

110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
With sulfonated styrene-divinylbenzene copolymer acidic cation exchange resin (D005) at 130℃; under 37503.8 Torr; Reagent/catalyst; Autoclave;
75-34-3

1,1-dichloroethane

110-71-4

1,2-dimethoxyethane

Conditions
ConditionsYield
In methanol73%
75-21-8

oxirane

67-56-1

methanol

201230-82-2

carbon monoxide

A

110-71-4

1,2-dimethoxyethane

B

6149-41-3

methyl ester (3-hydroxy) propionic acid

C

107-21-1

ethylene glycol

D

292638-85-8

acrylic acid methyl ester

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium tetracarbonylcobaltate at 75℃; under 27752.8 Torr; for 10h; Autoclave;
201230-82-2

carbon monoxide

A

67-56-1

methanol

B

71-23-8

propan-1-ol

C

110-71-4

1,2-dimethoxyethane

D

34557-54-5

methane

E

64-17-5

ethanol

F

74-84-0

ethane

G

78-83-1

2-methyl-propan-1-ol

H

107-31-3

Methyl formate

I

75-07-0

acetaldehyde

J

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen In carbon dioxide; nitrogen at 300℃; under 38787.1 Torr; for 20h; Conversion of starting material;
With hydrogen In carbon dioxide; nitrogen at 275℃; under 38787.1 Torr; for 22h; Conversion of starting material;
With hydrogen In carbon dioxide; nitrogen at 275℃; under 38787.1 Torr; for 22h; Conversion of starting material;
With hydrogen In carbon dioxide; nitrogen at 275℃; under 38787.1 Torr; for 20h; Conversion of starting material;
With hydrogen In carbon dioxide; nitrogen at 275℃; under 38787.1 Torr; for 20h; Conversion of starting material;
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Chemistry

Molecular Structure of 1,2-Dimethoxyethane (CAS NO.110-71-4):

 
Empirical Formula: C4H10O2
Molecular Weight: 90.121
IUPAC Name: 1,2-dimethoxyethane
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 18.46 Å2
Index of Refraction: 1.366
Molar Refractivity: 24.07 cm3
Molar Volume: 107.2 cm3
Surface Tension: 21.3 dyne/cm
Density: 0.839 g/cm3
Flash Point: 0 °C
Enthalpy of Vaporization: 32.42 kJ/mol
Boiling Point: 84.5 °C at 760 mmHg
Vapour Pressure: 80.6 mmHg at 25°C
Melting point: -69 °C
Storage temp: 2-8oC
Water Solubility: Miscible
Sensitive: Air Sensitive
Merck: 14,3224
BRN: 1209237
CAS: 110-71-4
InChI
InChI=1/C4H10O2/c1-5-3-4-6-2/h3-4H2,1-2H3
Smiles
C(COC)OC
Classification Code: Reproductive Effect
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

Uses

  1,2-Dimethoxyethane (CAS NO.110-71-4) is often used as a higher boiling alternative to diethyl ether and THF. As a bidentate ligand, it is used in organometallic chemistry like Grignard reactions, hydride reductions, and palladium-catalyzed reactions like Suzuki reactions and Stille coupling. It is also a good solvent for oligo- and polysaccharides. It is used as the low-viscosity component of the solvent for electrolytes of lithium batteries.

Production

(1)  2 CH3OCH2CH2OH + 2 Na → 2 CH3OCH2CH2ONa + H2↑ 
      CH3OCH2CH2ONa + CH3Cl → CH3OCH2CH2OCH3 + NaCl
(2)  CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 400mg/kg (400mg/kg)   National Technical Information Service. Vol. OTS0571323,
mouse LD50 oral 3200mg/kg (3200mg/kg)   National Technical Information Service. Vol. OTS0571323,
rabbit LDLo skin 2gm/kg (2000mg/kg)   National Technical Information Service. Vol. OTS0539769,
rat LCLo inhalation 63gm/m3/6H (63000mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: IRRITABILITY
National Technical Information Service. Vol. OTS0571323,
rat LD50 intraperitoneal 800mg/kg (800mg/kg)   National Technical Information Service. Vol. OTS0571323,
rat LDLo oral 1gm/kg (1000mg/kg)   National Technical Information Service. Vol. OTS0539769,

Consensus Reports

Reported in EPA TSCA Inventory. Glycol ether compounds are on the Community Right-To-Know List.

Safety Profile

Hazard Codes: FlammableF,ToxicT
Risk Statements: 60-61-11-19-20
60:  May impair fertility 
61:  May cause harm to the unborn child 
11:  Highly Flammable 
19:  May form explosive peroxides 
20:  Harmful by inhalation 
Safety Statements: 53-45
53:  Avoid exposure - obtain special instruction before use 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
RIDADR  UN: 2252 3/PG 2
WGK Germany: 1
RTECS:KI1451000
F: 3-10-23
HazardClass: 3
PackingGroup: II
HS Code: 29091900

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Specification

  1,2-Dimethoxyethane , with CAS number of 110-71-4, can be called 1,2-Ethanediol, dimethyl ether ; DME ; Dimethyl Cellosolve ; Ethylene dimethyl ether ; Ethylene glycol dimethyl ether ; Glyme ; Monoethylene glycol dimethyl ether ; Monoglyme ; Ethylene glycol dimethy ether ; a,b-Dimethoxyethane . 1,2-Dimethoxyethane (CAS NO.110-71-4)  should be stored in a tightly closed container. Make sure to keep from contact with oxidizing materials. It must be stored in a cool, dry, well-ventilated area away from incompatible substances. Flammables-area.