| Identification | More | [Name]
1,2-Dimethoxyethane | [CAS]
110-71-4 | [Synonyms]
1,2-DIMETHOXYETHANE
1,2-DIMETHYOXYETHANE
DIMETHYL CELLOSOLVE
DIMETHYLGLYCOL
DME
ETHYLENE GLYCOL DIMETHYL ETHER
MONOGLYME
1,2-dimethoxy-ethan
1,2-Ethanediol dimethyl ether
1,2-ethanediol,dimethylether
2,5-Dioxahexane
alpha,beta-Dimethoxyethane
Ansol E-121
Ansul ether 121
ansulether121
CH3OCH2CH2OCH3
Dimethoxyethane
dimethylcellosolvesolvent
Dimethylcollosolve
Egdme | [EINECS(EC#)]
203-794-9 | [Molecular Formula]
C4H10O2 | [MDL Number]
MFCD00008502 | [Molecular Weight]
90.12 | [MOL File]
110-71-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless liquid | [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.)
| [Fp ]
32 °F
| [storage temp. ]
2-8°C
| [solubility ]
1000g/l soluble | [form ]
Liquid | [color ]
Clear | [Odor]
water-wh. liq., sharp ethereal odor | [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. | [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 | [Detection Methods]
GC,NMR | [Merck ]
14,3224 | [BRN ]
1209237 | [Dielectric constant]
7.2（25℃） | [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]
110-71-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
F,T | [Risk Statements ]
R60:May impair fertility.
R61:May cause harm to the unborn child.
R11:Highly Flammable.
R19:May form explosive peroxides.
R20:Harmful by inhalation. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45: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 | [Autoignition Temperature]
396 °F | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29091900 | [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. | [Hazardous Substances Data]
110-71-4(Hazardous Substances Data) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Sodium hydroxide-->2-Methoxyethanol | [Preparation Products]
Azetidine-->3-N-Boc-amino-azetidine-->4-(Dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran-->Pigment Red 122-->3-AMINOBIPHENYL-->2-Aminoquinoline-->TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ISOINDOLINE-2-CARBOXYLATE-->4-BENZYL-MORPHOLINE-2-CARBOXYLIC ACID-->5-CHLORO-2'-DEOXYURIDINE-->2-Chloro-5-cyano-3-methylpyridine-->Quinacridone-->N,N-DIPHENYLQUINACRIDONE-->3,4-DICHLORO-N-METHYLANILINE-->4-CHLORO-7-METHYLTHIENO[3,2-D]PYRIMIDINE-->4'-BROMO-3'-FLUOROACETANILIDE-->2-PHENYLMALONAMIDE-->2-Bromo-5-hydroxypyridine radical ion(1+)-->EUROPIUM D-3-TRIFLUOROACETYLCAMPHORATE-->7-Methylthieno[3,2-d]pyrimidin-4(3H)-one-->2-CHLORO-5-IODO-3-METHYLPYRIDINE-->4-CHLORO-1,3-DIMETHYLPYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLIC ACID-->1-METHYL-1H-INDOLE-5-BORONIC ACID 2,2-DIMETHYL PROPANE DIOL-1,3-CYCLIC ESTER-->THIOPHENE-2,5-DICARBOXYLIC ACID MONOMETHYL ESTER-->N,N'-Dimethylquinacridone-->3-TRIFLUOROACETYL-D-CAMPHOR-->10-UNDECYNOIC ACID-->Tetrahydrocurcumin-->TERT-BUTYL 4-(4-FORMYL-1,3-THIAZOL-2-YL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE-->TERT-BUTYL 4-(5-FORMYL-4-METHYL-1,3-THIAZOL-2-YL)PIPERIDINE-1-CARBOXYLATE-->Beraprost-->TEMAFLOXACIN-->Sarafloxacin-->ETHYL 4-METHOXY-3-OXO-BUTANOATE-->4-Thiazolecarboxylic acid-->1,1,1-TRICHLOROACETONE-->5-FORMYL-2-THIOPHENECARBOXYLIC ACID-->2,3,5,6-Tetrafluorobenzyl alcohol-->2,3,5,6-Tetrafluoro-4-methylbenzyl alcohol |
| Hazard Information | Back Directory | [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. | [Reactivity Profile]
When the solvent, 1,2-DIMETHOXYETHANE(110-71-4), was poured into a funnel previously used to introduce the lithium aluminum hydride, a fire ignited the funnel, [MCA Case History 1182(1966)]. | [Air & Water Reactions]
Highly flammable. Slightly soluble in water. | [Hazard]
Moderate fire risk. | [Health Hazard]
If ingested causes nausea, vomiting, cramps, weakness, coma. | [Fire Hazard]
Behavior in Fire: Containers may explode in fires. | [Description]
1,2-Dimethoxyethane (DME) is a liquid ether used as 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 is higher boiling than diethyl ether and THF[1]. | [Chemical Properties]
Colorless liquid | [Uses]
Monoglyme is used in the electrolyte solutions for lithium batteries. | [Uses]
Solvent commonly employed in organometallic reactions,1 particularly organolithium reactions.2 May also function as a ligand.3 | [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. | [Definition]
ChEBI: A diether that is the 1,2-dimethyl ether of ethane-1,2-diol. | [Flammability and Explosibility]
Highlyflammable | [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.
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