112-36-7

Basic information

• Product Name: 2-Ethoxyethyl ether
• Synonyms: 1,1’-oxybis(2-ethoxy-ethan;1,1’-oxybis[2-ethoxy-ethan;1,1’-oxybis[2-ethoxy-Ethane;1-Ethoxy-2-(2-ethoxyethoxy)ethane;1-ethoxy-2-(2-ethoxy-ethoxy)-ethane;1-ethoxy-2-(2-ethoxyethoxy)-ethane;1-Ethoxy-2-(beta-ethoxyethoxy)ethane;2-(2-Ethoxyethoxy)-1-ethoxyethane
• CAS NO: 112-36-7
• Molecular Formula: C₈H₁₈O₃
• Molecular Weight: 162.23
• EINECS: 203-963-7
• Product Categories: Polyalcohol Ethers, Esters (Plasticizer);Functional Materials;Plasticizer;ACS and Reagent Grade Solvents;Amber Glass Bottles;Carbon Steel Flex-Spout Cans;Reagent;Reagent Grade Solvents;Semi-Bulk Solvents;Solvent Bottles;Solvent by Application;Solvent Packaging Options;Solvents;Ether
• Mol File: 112-36-7.mol

Chemical Properties

• Melting Point: -44.3 °C
• Boiling Point: 180-190 °C(lit.)
• Flash Point: 160 °F
• Appearance: Clear/Liquid
• Density: 0.909 g/mL at 25 °C(lit.)
• Vapor Density: 5.6 (vs air)
• Vapor Pressure: 0.5 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.412(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: SOLUBLE
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents. May form peroxides on exposure to air - test for their presence
• Merck: 14,3118
• BRN: 1699259
• CAS DataBase Reference: 2-Ethoxyethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethoxyethyl ether(112-36-7)
• EPA Substance Registry System: 2-Ethoxyethyl ether(112-36-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36-19
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: KN3160000
• TSCA: Yes
• Hazardous Substances Data: 112-36-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
2-Ethoxyethyl ether is used as a solvent for various chemical reactions, taking advantage of its high boiling point and ability to dissolve a wide range of substances.
Used in Enzyme Activity Studies:
In the field of biochemistry, 2-Ethoxyethyl ether is utilized as a high boiling reaction medium to study the activities of enzymes in aqueous organic mixtures, providing a suitable environment for enzyme-catalyzed reactions to occur.
Used in Research and Laboratory Settings:
Due to its properties as a colorless liquid and a versatile solvent, 2-Ethoxyethyl ether is employed in research and laboratory settings for conducting experiments and handling sensitive compounds that require a stable and inert medium.

Air & Water Reactions

Highly flammable. May be sensitive to prolonged exposure to air. Can form explosive peroxides. Vapor-air mixtures are explosive above the flash point. Water soluble.

Reactivity Profile

2-Ethoxyethyl ether is incompatible with strong acids. 2-Ethoxyethyl ether is also incompatible with strong oxidizing agents.

Fire Hazard

2-Ethoxyethyl ether is combustible.

Safety Profile

Moderately toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. An eye irritant. Flammable when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.

Purification Methods

Dry the ether with MgSO4, then CaH2 or LiAlH4, under N2. If sodium is used, the ether should be redistilled alone to remove any products which may be formed by the action of sodium on the ether. As a preliminary purification, the crude ether (2L) can be refluxed for 12hours with 25mL of conc HCl in 200mL of water, under reduced pressure, with slow passage of N2 to remove aldehydes and other volatile substances. After cooling, add sufficient solid KOH pellets (slowly and with shaking until no more dissolves) to give two liquid phases. The upper of these is decanted, dried with fresh KOH pellets, decanted, then refluxed over, and distilled from sodium. It can be passed through (alkaline) alumina prior to purification. [Beilstein 1 IV 2394.]

InChI:InChI:1S/C8H18O3/c1-3-9-5-7-11-8-6-10-4-2/h3-8H2,1-2H3

Upstream product

• 56-23-5 tetrachloromethane 
• 592-55-2 2-Bromoethyl ethyl ether 
• 64-17-5 ethanol 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 141-52-6 sodium ethanolate 
• 359-21-7 (E/Z)-1,2-dibromo-1,2-difluoroethylene 
• 16993-83-2 sodium 2-ethoxyethoxide 
• 75-03-6 ethyl iodide 
• 111-46-6 diethylene glycol 
• 123-91-1 1,4-dioxane 
• 60-29-7 diethyl ether 
• 111-77-3 2-(2-methoxyethoxy)ethyl alcohol 
• 111-90-0 ethoxyethoxyethanol 
• 110-80-5 2-ethoxy-ethanol 

Downstream Products

• 60-12-8 2-phenylethanol 
• 50844-81-0 (2-Methyl-3,4-dihydro-4-oxoquinazolin-3-yl)acetic acid 
• 26196-04-3 1-methoxy-2-methylpropylene oxide 
• 101090-25-9 phenyl-(2,4,6-trimethyl-3-nitro-phenyl)-ether 
• 71-23-8 propan-1-ol 
• 34557-54-5 methane 
• 64-17-5 ethanol 
• 90909-58-3 6H-2-chloro-dibenzopyran-6-one 
• 1849-29-2 1,1,1-trideuteromethanol 
• 67-63-0 isopropyl alcohol 
• 463-49-0 1,2-propanediene 
• 74-99-7 prop-1-yne 
• 2999-74-8 dimethylmagnesium 
• 78-78-4 methylbutane 

Relevant articles and documents

METHOD FOR PRODUCING (POLY)ALKYLENE GLYCOL DIALKYL ETHER

PROBLEM TO BE SOLVED: To provide a method for producing a (poly)alkylene glycol dialkyl ether which further contributes the reduction of waste. SOLUTION: There is provided a method for producing a (poly)alkylene glycol dialkyl ether by reacting 1,4-dioxane and a dialkyl ether represented by the following general formula: R1-O-(AO)n-R2 (in the formula, R1 and R2 each independently represents a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 8 carbon atoms which may have a substituent, an aryl group having 6 to 8 carbon atoms which may have a substituent; A represents a linear or branched alkylene group having 2 to 4 carbon atoms, n represents an addition mole number of an oxyalkylene group; and n represents an integer of 0 to 5.) COPYRIGHT: (C)2016,JPOandINPIT

A method of manufacturing an alkylene glycol ether (poly)

PROBLEM TO BE SOLVED: To provide a method for producing a (poly)alkylene glycol diether, introducing the oxyalkylene groups of the optional mole number of addition and optional terminal alkyl groups by using a metallosilicate catalyst having 10 to 1,000 ratio of SiO2/M2O3as an ether interchange reaction catalyst. SOLUTION: This method for producing the (poly)alkylene glycol diether includes a process of obtaining the (poly)alkylene glycol diether by the ether interchange reaction of a first (poly)alkylene glycol monoether with a second (poly)alkylene glycol monoether in the presence of the metallosilicate catalyst having 10 to 1,000 ratio of SiO2/M2O3(wherein, M is ≥1 kind selected from the group consisting of Al, Ga, Ge, B, Zn, P, Zr, Ti, Cr, Be, V and As). COPYRIGHT: (C)2012,JPOandINPIT

Vinylic Substitution of 1,2-Dibromo-1,2-difluoroethylene and Tribromofluoroethylene. An Intramolecular kBr/kF Element Effect and Apparent Inversion of Configuration in SNV Reactions

The reactions of (E/Z)-1,2-dibromo-1,2-difluoroethylene(1) and of tribromofluoroethylene (2) with alkoxide ions and of 1 with p-toluenethiolate ion give multiplicity of products.The reaction of 1 with 1 equiv of NaOMe gives mainly a 2:1 mixture of the product of one bromine displacement, together with methyl dimethoxyacetate (3), methyl bromofluoroacetate (4), 1,1,2-trifluoro-2-bromoethyl ether (7), and 1,1-difluoro-1,2,2-trimethoxyethane (8).With 2 equiv of MeO(1-) 3 and 4 are the main products, and at 130 deg C, dimethyl ether 5 is also formed.With EtOCH2CH2O(1-) 1 gave 2-ethoxyethyl bromofluoroacetate (9), bis(2-ethoxyethyl) ether (10), and E/Z mixtures of the substitution products EtOCH2CH2OC(F)=C(F)Br (12) and EtOCH2CH2OC(Br)=C(F)Br (13).Reaction of 2 with excess RO(1-) (R = Me, Et) gives alkyl dibromoacetates, while with 1 equiv of RO(1-) only a bromine from the =C(F)Br carbon is displaced.Reaction of 1 with p-TolSNa in MeOH gives the reduction-substitution product p-TolSC(F)=CHF (18), together with (P-TolS)2 (16) and p-TolSMe (17).The same reaction in DMSO gives E/Z mixtures of the product of displacement of one bromine (19) or two bromines (20).Formation of the products is rationalized by an initial nucleophilic attack on the vinylic carbon followed by leaving group expulsion, giving, e.g., 12, 13, 19, or 20.Hydrolysis of the intermediate or addition of HF to the initial substition product gives saturated products, e.g., 3, 4, 7, or 8, while SN2 reactions on the ether oxygen give ethers 5 and 10.A bromophilic reaction gives the reduction-substitution product 18, while hydrolysis-decarboxylation leads to 17.The regiospecificity of the nucleophilic addition is due to polar and hyperconjugative effects.An intramolecular element effect kBr/kF of > 10 is reported for the first time in the reaction of 1 with EtOCH2CH2O(1-).This value and the absence of such effects in other reactions are consistent with a much higher nucleofugality from a (1-)CC(F)Br system of Br(1-) compared with F(1-).The E/Z compositions of 18-20 indicates an apparent inversion in their formation, but it is not known whether these compositions are thermodynamically or kinetically controlled.

SYNTHESIS OF DIALKYL ETHERS OF POLYETHYLENE GLYCOLS

Methods were developed for synthesis of dimethyl and diethyl ethers of polyethylene glycols in one step (without isolation of intermediates) with the general formula R(OC2H4)mOR, where R=CH3, C2H5 and m=2-6 (degree of polyglycolicity).As starting materials monomethyl and monoethyl ethers of polyethylene glycols of the formula R(OC2H4)nOH were used, where n=1-3.As reagents toluenesulfonyl chloride and methanesulfonyl chloride were used.

Veretherungen von Diolen, Triolen und Hydroxycarbonsaeurederivaten ueber Thallium(I)-alkoholate. Eine neue Variante der Williamson-Reaktion

The etherifications listed in tables 1 and 2 are achieved by converting hydroxy-derivatives, which contain additional oxygen functions, into thallium(I) alkoxides with thallium ethoxide, and treatment with haloalkanes.The scope and limitations of the method are discussed.