3386-87-6

Basic information

• Product Name: ETHYLENE GLYCOL BIS(PROPIONITRILE) ETHER
• Synonyms: 3,3'-(ETHYLENEDIOXY)DIPROPIONITRILE;1,2-BIS(2-CYANOETHOXY)ETHANE;ETHYLENE GLYCOL BIS(2-CYANOETHYL) ETHER;ETHYLENE GLYCOL BIS(PROPIONITRILE) ETHER;LABOTEST-BB LT00044435;Propanenitrile,3,3’-[1,2-ethanediylbis(oxy)]bis-;3,3'-(ethylenedioxy)dipropiononitrile;liquidphaseforGC
• CAS NO: 3386-87-6
• Molecular Formula: C₈H₁₂N₂O₂
• Molecular Weight: 168.19
• EINECS: 222-208-2
• Product Categories: Dinitriles;Dinitriles & Trinitriles;Fine Chemical;pharmaceutical
• Mol File: 3386-87-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 165 °C / 5mmHg
• Flash Point: 154 °C
• Appearance: /
• Density: 1,07 g/cm3
• Refractive Index: 1.4470 to 1.4510
• CAS DataBase Reference: ETHYLENE GLYCOL BIS(PROPIONITRILE) ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYLENE GLYCOL BIS(PROPIONITRILE) ETHER(3386-87-6)
• EPA Substance Registry System: ETHYLENE GLYCOL BIS(PROPIONITRILE) ETHER(3386-87-6)

Safety Data

• Statements: 23/24/25
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 3386-87-6(Hazardous Substances Data)

Usage

General Description

ETHYLENE GLYCOL BIS(PROPIONITRILE) ETHER is a chemical compound that is commonly used as a solvent in industrial and laboratory applications. It is a clear, colorless liquid with low viscosity and a high boiling point, making it suitable for a wide range of uses. ETHYLENE GLYCOL BIS(PROPIONITRILE) ETHER is primarily used as a solvent in the formulation of paints, coatings, and adhesives, as well as in the production of specialty chemicals and pharmaceuticals. It has good solubility properties and is compatible with a variety of other solvents and chemicals, making it a versatile option for many different applications. Additionally, it is known for its low toxicity and low volatility, making it a relatively safe and stable option for use in various processes.

Synthetic route

ethylene glycol (107-21-1) + acrylonitrile (107-13-1) → 1,2-bis-(2-cyanoethoxy)ethane (3386-87-6)

Conditions	Yield
With sodium hydroxide In water 1. 0 deg C, 1h 2. 24h room temperature;	85%
With sodium hydroxide In water at 0 - 20℃;	85.8%
N-benzyl-trimethylammonium hydroxide In methanol at 20℃; for 60h; Cooling with ice;	50.9%

3-Chloropropionitrile (542-76-7) + ethylene glycol (107-21-1) → 3-(2-hydroxyethyloxy)propanenitrile (24298-26-8) + 1,2-bis-(2-cyanoethoxy)ethane (3386-87-6)

Conditions	Yield
With sodium hydroxide 1) benzene, 70 to 80 deg C, 4 h; 2) 3 h.; Yield given. Multistep reaction;	A 54.4% B n/a
With sodium hydroxide 1) benzene, 70 to 80 deg C, 4 h; 2) 3 h.; Yield given. Multistep reaction;	A n/a B 31.3%

sodium methylate (124-41-4) + ethylene glycol (107-21-1) + acrylonitrile (107-13-1) → 1,2-bis-(2-cyanoethoxy)ethane (3386-87-6)

Conditions	Yield
at 25 - 35℃;
at 25 - 35℃;

ethylene glycol (107-21-1) + acrylonitrile (107-13-1) + KOH-solution → 1,2-bis-(2-cyanoethoxy)ethane (3386-87-6)

Conditions	Yield
at 25 - 35℃;
at 25 - 35℃;

acetaldehyde (75-07-0) + 3-Hydroxypropionitrile (109-78-4) → 1,2-bis-(2-cyanoethoxy)ethane (3386-87-6)

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane

ethylene glycol (107-21-1) + acrylonitrile (107-13-1) → 2-cyanoethyl ether (1656-48-0) + 1,2-bis-(2-cyanoethoxy)ethane (3386-87-6)

Conditions	Yield
Stage #1: ethylene glycol With sodium hydroxide In water at 40℃; Stage #2: acrylonitrile for 4h;

ethylene glycol (dipropylamide) ether (93930-31-5) → 1,2-bis-(2-cyanoethoxy)ethane (3386-87-6)

Conditions	Yield
With thionyl chloride In 1,2-dichloro-ethane at 70 - 80℃; for 4h; Solvent; Temperature;	175 g

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 3,3'-(ethane-1,2-diylbis(oxy))bis(N'-hydroxypropanimidamide) (1146973-35-4)

Conditions	Yield
With NH2OH In ethanol; water	100%

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 3,3'-(ethane-1,2-diylbis(oxy))bis(N'-hydroxypropanimidamide) (1146973-35-4)

Conditions	Yield
With hydroxylamine In ethanol; water at 80℃; for 24h;	100%

ethanol (64-17-5) + 1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → diethyl 3,3'-(ethane-1,2-diylbis(oxy))dipropanoate (75315-97-8)

Conditions	Yield
With sulfuric acid 1. 0 deg C 2. 24h reflux;	84%
With sulfuric acid at 85℃; for 16h;	45%
With sulfuric acid at 85℃; for 16h;	45%
With sulfuric acid Behandeln des Reaktionsgemisches mit Wasser;
With sulfuric acid Reflux;

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → ethylene glycol (dipropylamide) ether (93930-31-5) + 4,7-dioxa-9-cyanononanamide (105380-12-9)

Conditions	Yield
With weakly alkaline medium (pH 8-9); dihydrogen peroxide Heating;	A 40% B 49%
With dihydrogen peroxide Heating; weakly alkaline medium (pH 8-9);	A 40% B 49%

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 5,5′-[ethane-1,2-diylbis(oxyethane-2,1-diyl)]di(1H-tetrazole) (66012-58-6)

Conditions	Yield
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 90 - 100℃; for 10h;	15%
With sodium azide; ammonium chloride In N,N-dimethyl-formamide 100 deg C, 6-8 h, then 120 deg C, 20-25 h;

4,4-dimethyl-1,3-dioxane (766-15-4) + 1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 1,2-di{β-[2-(4,4-dimethyl-5,6-dihydro-2-oxazinyl)]ethoxy}ethane

Conditions	Yield
With sulfuric acid In 1,4-dioxane; hexane at 20℃; for 24h;	10%

methanol (67-56-1) + 1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → dimethyl 4,7-dioxadecane-1,10-dioate (51365-50-5)

Conditions	Yield
With sulfuric acid Behandeln des Reaktionsgemisches mit Wasser;
With toluene-4-sulfonic acid Heating;
acid

2-ethoxy-ethanol (110-80-5) + 1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 4,7-dioxa-decanedioic acid bis-(2-ethoxy-ethyl ester) (61286-34-8)

Conditions	Yield
/BRN= 1802416/;

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 1,2-bis(3-aminopropoxy)ethane (2997-01-5)

Conditions	Yield
With ammonia; cobalt at 90 - 100℃; Hydrogenation.unter Druck;
With ammonia; nickel at 90 - 100℃; Hydrogenation.unter Druck;

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → ethylene glycol (dipropylamide) ether (93930-31-5)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 4,7-dioxa-decanedioic acid bis-(2-ethyl-butyl ester)

Conditions	Yield
With sulfuric acid Kochen des Reaktionsprodukts mit 2-Aethyl-butanol-(1) und Toluol;

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 4,7-dioxa-decanedioic acid bis-(1-methyl-heptyl ester)

Conditions	Yield
With sulfuric acid at 60℃; Kochen des Reaktionsprodukts mit Octanol-(2) + Toluol;

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 3,3'-ethanediyldioxy-di-propionic acid dicyclohexyl ester

Conditions	Yield
With sulfuric acid at 60 - 70℃; Kochen des Reaktionsprodukts mit Cyclohexanol und Toluol;

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 3,3'-(ethane-1,2-diylbis(oxy))dipropanoic acid (19364-66-0)

Conditions	Yield
With hydrogenchloride for 0.0833333h; Heating;
Multi-step reaction with 2 steps 1: sulfuric acid / 16 h / 85 °C 2: potassium hydroxide / water; ethanol / 1 h / 85 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / 16 h / 85 °C 2: water; potassium hydroxide / ethanol / 1 h / 85 °C View Scheme

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) + acetylene (74-86-2) → 3-[2-(2-Pyridin-2-yl-ethoxy)-ethoxy]-propionitrile (102195-58-4) + C16H20N2O2 (102195-59-5)

Conditions	Yield
With triethylaluminum; cobalt(II) 2-ethylhexanoate In toluene at 150℃; under 11400 Torr; for 10h;	A 70 % Turnov. B 30 % Turnov.

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → vinyloxypropionitrile (15678-32-7)

Conditions	Yield
With sodium hydrogen sulfate

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 2'-O-[1-(2-cyanoethoxy)ethyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (213548-64-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogen sulfate 2: 94 percent / p-toluenesulfonic acid / dioxane View Scheme

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → N-(1-{(2R,3R,3aR,9aR)-3-[1-(2-Cyano-ethoxy)-ethoxy]-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-acetamide (828247-67-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogen sulfate 2: 97 percent / p-toluenesulfonic acid / dioxane View Scheme

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → N-(9-{(2R,3R,3aR,9aR)-3-[1-(2-Cyano-ethoxy)-ethoxy]-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl}-9H-purin-6-yl)-acetamide (828247-66-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogen sulfate 2: 96 percent / p-toluenesulfonic acid / dioxane View Scheme

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → 3-{1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-yloxy]-ethoxy}-propionitrile (828247-82-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydrogen sulfate 2.1: 94 percent / p-toluenesulfonic acid / dioxane 3.1: tetrabutylammonium fluoride; acetic acid / tetrahydrofuran 3.2: 85 percent / pyridine View Scheme

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → N-(1-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-[1-(2-cyano-ethoxy)-ethoxy]-4-hydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-acetamide (828247-75-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydrogen sulfate 2.1: 97 percent / p-toluenesulfonic acid / dioxane 3.1: tetrabutylammonium fluoride; acetic acid / tetrahydrofuran 3.2: 90 percent / pyridine View Scheme

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-[1-(2-cyano-ethoxy)-ethoxy]-4-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-acetamide (828247-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydrogen sulfate 2.1: 96 percent / p-toluenesulfonic acid / dioxane 3.1: tetrabutylammonium fluoride; acetic acid / tetrahydrofuran 3.2: 96 percent / pyridine View Scheme

1,2-bis-(2-cyanoethoxy)ethane (3386-87-6) → phosphoric acid 4-[1-(2-cyano-ethoxy)-ethoxy]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester 5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium hydrogen sulfate 2.1: 94 percent / p-toluenesulfonic acid / dioxane 3.1: tetrabutylammonium fluoride; acetic acid / tetrahydrofuran 3.2: 85 percent / pyridine 4.1: 82 percent / diisopropylethylamine / CH2Cl2 5.1: 1H-tetrazole / acetonitrile 5.2: 100 percent / tert-butylhydroperoxide 6.1: dichloroacetic acid / CH2Cl2 7.1: aq.NH3 / ethanol View Scheme

Upstream product

• 124-41-4 sodium methylate 
• 107-21-1 ethylene glycol 
• 107-13-1 acrylonitrile 
• 93930-31-5 ethylene glycol (dipropylamide) ether 
• 75-07-0 acetaldehyde 
• 109-78-4 3-Hydroxypropionitrile 
• 542-76-7 3-Chloropropionitrile 

Downstream Products

• 75315-97-8 diethyl 3,3'-(ethane-1,2-diylbis(oxy))dipropanoate 
• 886362-90-9 3-(2-(3-ethoxy-3-oxopropoxy)ethoxy)propanoic acid 
• 2997-01-5 1,2-bis(3-aminopropoxy)ethane 
• 108-10-1 4-methyl-2-pentanone 
• 126277-55-2 trans-(2S,3S)-(-)-2,3-bis(toluene-p-sulfonyloxymethyl)-1,4,8,11-tetraoxacyclotetradecane 
• 126277-52-9 (2S,3S)-(-)-2,3-bis(benzyloxymethyl)-1,4,8,11-tetraoxacyclotetradecane 
• 107106-21-8 2-toluene-p-sulfonyloxymethyl-1,4,8,11-tetraoxacyclotetradecane 
• 92818-19-4 2-benzyloxymethyl-1,4,8,11-tetraoxacyclotetradecane 
• 847979-67-3 C₆₃H₆₃N₆O₂₁P 
• 828247-89-8 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[1-(2-cyano-ethoxy)-ethoxy]-5-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 828247-85-4 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(6-acetylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[1-(2-cyano-ethoxy)-ethoxy]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 828247-88-7 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[1-(2-cyano-ethoxy)-ethoxy]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 828247-78-5 N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-[1-(2-cyano-ethoxy)-ethoxy]-4-hydroxy-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenoxy-acetamide 
• 828247-90-1 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[1-(2-cyano-ethoxy)-ethoxy]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 

Relevant articles and documents

Glycol (propionitrile) preparation method of the ether (by machine translation)

The invention discloses glycol (propionitrile) preparation method of the ether, preparation steps are as follows: in order to ethylene glycol and acrylonitrile as the reaction raw materials, the reaction temperature 30 °C -70 °C, and the catalyst solution in the catalysis of the reaction generating glycol (propionitrile) ether, the catalyst solution is composite alkali catalyst aqueous solution, the aqueous solution of alkali catalyst composite by triethyl benzyl ammonium hydroxide aqueous solution is mixed with the aqueous solution of sodium hydroxide. Because the alkaline lower triethyl benzyl ammonium hydroxide aqueous solution and aqueous sodium hydroxide solution formed by mixing the aqueous solution of the composite alkali catalyst, so that the reaction solution in the alkaline greatly reduced, thus greatly reducing the generation of by-product double-c nitrile ether, such ethylene glycol-ether (propionitrile) molar yield will be greatly improved, molar yield can reach 90% or more, and can more easily purification to obtain high purity glycol (propionitrile) ether, its purity can reach 95% or more. (by machine translation)

METHOD FOR PREPARING A DINITRILE COMPOUND

Disclosed is a method for preparing a dinitrile compound. The method includes reacting an alcohol compound with a nitrile compound having a terminal carbon-carbon unsaturated bond under anhydrous conditions. A potassium alkoxide having 1 to 5 carbon atoms is used as a catalyst in the course of the reaction. According to the method, a high-purity dinitrile compound can be prepared in a simple manner within a short reaction time indicating high productivity.

Synthesis and intrinsic blue fluorescence study of hyperbranched poly(ester-amide-ether)

A series of hyperbranched poly(ester-amide-ether)s (H-PEAEs) were synthesized via the A2+CB3 approach by the self-transesterification of ethyl ester-amide-ethers end-capped with three hydroxyl groups and ethyl ester group at two terminals. The molecular structures were characterized with 1H NMR and FT-IR spectroscopy. The number average molecular weights were estimated by GPC analysis to possess bimodal wide distribution from 1.57 to 2.09. The strong inherent blue fluorescence was observed at 330 nm for excitation and 390 nm for emission. Moreover, the emission intensity and fluorescence quantum yield increased along with the incorporated ether chain length, as well as almost linearly with the H-PEAE concentration in an aqueous solution. For comparing the fluorescence performance, the linear poly(ester-amide-ether) (L-PEAE) and hyperbranched poly(ester-amide) (H-PEA) were synthesized. The results showed that the coexistence of ether bond and carboxyl group in the molecular chain was essential for generating the strong fluorescence. However, the compact backbone of H-PEAE would be propitious to the enhancement of fluorescence properties.