Propanenitrile,3,3'-[1,2-ethanediylbis(oxy)]bis- supplier

Name
ETHYLENE GLYCOL BIS(PROPIONITRILE) ETHER
EINECS 222-208-2
CAS No. 3386-87-6
Article Data29
CAS DataBase
Density 1.05 g/cm³
Solubility
Melting Point
Formula C₈H₁₂N₂O₂
Boiling Point 358.5 °C at 760 mmHg
Molecular Weight 168.195
Flash Point 154 °C
Transport Information UN 3276
Appearance
Safety 26-36/37/39
Risk Codes 23/24/25
Molecular Structure
Hazard Symbols
Synonyms Propionitrile,3,3'-(ethylenedioxy)di- (6CI,7CI,8CI);1,2-Bis(2-cyanoethoxy)ethane;1,2-Bis(b-cyanoethoxy)ethane;3,3'-(Ethylenedioxy)dipropionitrile;3,6-Dioxa-1,8-dicyanooctane;Ethyleneglycol bis(2-cyanoethyl) ether;Ethylene glycol di-b-cyanoethyl ether;NSC 69063;
PSA 66.04000
LogP 0.84696

Synthetic route

: 107-21-1
ethylene glycol

: 107-13-1
acrylonitrile

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

Conditions

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%

: 542-76-7
3-Chloropropionitrile

: 107-21-1
ethylene glycol

A: 24298-26-8
3-(2-hydroxyethyloxy)propanenitrile

B: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

Conditions

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%

...Expand

: 124-41-4
sodium methylate

: 107-21-1
ethylene glycol

: 107-13-1
acrylonitrile

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

Conditions

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

...Expand

: 107-21-1
ethylene glycol

: 107-13-1
acrylonitrile

KOH-solution: KOH-solution

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

Conditions

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

...Expand

: 75-07-0
acetaldehyde

: 109-78-4
3-Hydroxypropionitrile

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

Conditions

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

: 107-21-1
ethylene glycol

: 107-13-1
acrylonitrile

A: 1656-48-0
2-cyanoethyl ether

B: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

Conditions

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

...Expand

: 93930-31-5
ethylene glycol (dipropylamide) ether

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 1146973-35-4
3,3'-(ethane-1,2-diylbis(oxy))bis(N'-hydroxypropanimidamide)

Conditions

Conditions	Yield
With NH2OH In ethanol; water	100%

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 1146973-35-4
3,3'-(ethane-1,2-diylbis(oxy))bis(N'-hydroxypropanimidamide)

Conditions

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

: 64-17-5
ethanol

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 75315-97-8
diethyl 3,3'-(ethane-1,2-diylbis(oxy))dipropanoate

Conditions

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;

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

A: 93930-31-5
ethylene glycol (dipropylamide) ether

B: 105380-12-9
4,7-dioxa-9-cyanononanamide

Conditions

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%

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 66012-58-6
5,5′-[ethane-1,2-diylbis(oxyethane-2,1-diyl)]di(1H-tetrazole)

Conditions

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;

: 766-15-4
4,4-dimethyl-1,3-dioxane

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 1,2-di{β-[2-(4,4-dimethyl-5,6-dihydro-2-oxazinyl)]ethoxy}ethane

Conditions

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

: 67-56-1
methanol

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 51365-50-5
dimethyl 4,7-dioxadecane-1,10-dioate

Conditions

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

: 110-80-5
2-ethoxy-ethanol

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 61286-34-8
4,7-dioxa-decanedioic acid bis-(2-ethoxy-ethyl ester)

Conditions

Conditions	Yield
/BRN= 1802416/;

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 2997-01-5
1,2-bis(3-aminopropoxy)ethane

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 93930-31-5
ethylene glycol (dipropylamide) ether

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 4,7-dioxa-decanedioic acid bis-(2-ethyl-butyl ester)

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 4,7-dioxa-decanedioic acid bis-(1-methyl-heptyl ester)

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 3,3'-ethanediyldioxy-di-propionic acid dicyclohexyl ester

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 19364-66-0
3,3'-(ethane-1,2-diylbis(oxy))dipropanoic acid

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 74-86-2
acetylene

A: 102195-58-4
3-[2-(2-Pyridin-2-yl-ethoxy)-ethoxy]-propionitrile

B: 102195-59-5
C16H20N2O2

Conditions

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

...Expand

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 15678-32-7
vinyloxypropionitrile

Conditions

Conditions	Yield
With sodium hydrogen sulfate

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 213548-64-2
2'-O-[1-(2-cyanoethoxy)ethyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 828247-67-2
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

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 828247-66-1
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

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 828247-82-1
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

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 828247-75-2
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

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 828247-72-9
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

Conditions

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

: 3386-87-6
1,2-bis-(2-cyanoethoxy)ethane

: 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

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

Propanenitrile,3,3'-[1,2-ethanediylbis(oxy)]bis- Specification

The CAS registry number of Propanenitrile,3,3'-[1,2-ethanediylbis(oxy)]bis- is 3386-87-6. It belongs to the product categories of Dinitriles; Dinitriles & Trinitriles. This chemical is also named as 3,3'-[Ethane-1,2-diylbis(oxy)]dipropanenitrile. Its EINECS registry number is 222-208-2. In addition, its molecular formula is C₈H₁₂N₂O₂ and molecular weight is 168.19. Its IUPAC name is called 3-[2-(2-cyanoethoxy)ethoxy]propanenitrile.

Physical properties about Propanenitrile,3,3'-[1,2-ethanediylbis(oxy)]bis- are: (1)ACD/LogP: -1.15; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.15; (4)ACD/LogD (pH 7.4): -1.15; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 5.63; (8)ACD/KOC (pH 7.4): 5.63; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.442; (13)Molar Refractivity: 42.42 cm³; (14)Molar Volume: 160 cm³; (15)Surface Tension: 41.5 dyne/cm; (16)Density: 1.05 g/cm³; (17)Flash Point: 154 °C; (18)Enthalpy of Vaporization: 60.4 kJ/mol; (19)Boiling Point: 358.5 °C at 760 mmHg.

Preparation: this chemical can be prepared by ethane-1,2-diol and acrylonitrile. This reaction will need catalyst potassium hydroxide and solvent benzene. The reaction time is 1 hour at ambient temperature.

Uses of Propanenitrile,3,3'-[1,2-ethanediylbis(oxy)]bis-: it can be used to produce 4,7-dioxa-decanedioic acid diethyl ester at temperature of 0 °C. It will need solvent H₂SO₄. This reaction will need 24 h reflux.

Propanenitrile,3,3'-[1,2-ethanediylbis(oxy)]bis- can be used to produce 4,7-dioxa-decanedioic acid diethyl ester

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic by inhalation, in contact with skin and if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: N#CCCOCCOCCC#N
(2)InChI: InChI=1/C8H12N2O2/c9-3-1-5-11-7-8-12-6-2-4-10/h1-2,5-8H2
(3)InChIKey: VTHRQKSLPFJQHN-UHFFFAOYAZ

Product Name

ETHYLENE GLYCOL BIS(PROPIONITRILE) ETHER

Synthetic route

Propanenitrile,3,3'-[1,2-ethanediylbis(oxy)]bis- Specification

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