56011-12-2

Basic information

• Product Name: 2,2-DIETHOXYPROPIONITRILE
• Synonyms: 2,2'-DIETHOXYPROPIONITRILE;2,2-DIETHOXYPROPIONITRILE;2,2'-DIETHOXYPROPANENITRILE;2,2-DIETHOXYPROPANENITRILE
• CAS NO: 56011-12-2
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.18
• Product Categories: Miscellaneous;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 56011-12-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 60 °C20 mm Hg(lit.)
• Flash Point: 112 °F
• Appearance: /
• Density: 0.918 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.82mmHg at 25°C
• Refractive Index: n20/D 1.398(lit.)
• CAS DataBase Reference: 2,2-DIETHOXYPROPIONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIETHOXYPROPIONITRILE(56011-12-2)
• EPA Substance Registry System: 2,2-DIETHOXYPROPIONITRILE(56011-12-2)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 56011-12-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to light brown liquid

Synthesis Reference(s)

Synthesis, p. 498, 1983 DOI: 10.1055/s-1983-30402

InChI:InChI=1/C7H13NO2/c1-4-9-7(3,6-8)10-5-2/h4-5H2,1-3H3

Synthetic route

trimethylsilyl cyanide (7677-24-9) + Triethyl orthoacetate (78-39-7) → 2,2-diethoxypropanenitrile (56011-12-2)

Conditions	Yield
With zinc(II) iodide at 10 - 15℃; for 5h; Inert atmosphere;	96%
zinc(II) chloride at 25℃; for 3h;	84%

2-ethoxyacrylonitrile (19479-65-3) + ethanol (64-17-5) → 2,2-diethoxypropanenitrile (56011-12-2)

Conditions	Yield
With sodium methylate

hydrogen cyanide (74-90-8) + Triethyl orthoacetate (78-39-7) → 2,2-diethoxypropanenitrile (56011-12-2)

Conditions	Yield
With zinc(II) chloride
With sulfur dioxide; zinc(II) chloride

2-ethoxy-3-bromo-propionitrile (87271-69-0) → 2,2-diethoxypropanenitrile (56011-12-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethylamine; diethyl ether 2: sodium methylate View Scheme

2,2-diethoxypropanenitrile (56011-12-2) → 2,2-diethoxypropanethioamide

Conditions	Yield
With sodium hydrogen sulfide monohydrate; triethylamine hydrochloride In tetrahydrofuran; ethanol at 20℃; for 12h; Kinetics; Reagent/catalyst; Solvent; Inert atmosphere;	87%
With pyridine; diammonium sulfide In water at 20℃; for 18h; Inert atmosphere;	84%

2,2-diethoxypropanenitrile (56011-12-2) → 2,2-diethoxy-N'-hydroxypropanamidine (885965-30-0)

Conditions	Yield
With hydroxylamine hydrochloride; sodium carbonate In methanol; water for 17h; Reflux;	77%

(E)-2-(((2-styrylphenyl)amino)methyl)phenol (909297-33-2) + 2,2-diethoxypropanenitrile (56011-12-2) + tert.-butyl lithium (594-19-4) → 1-(1-benzyl-4-tert-butyl-3-phenyl-1,4-dihydroquinolin-2-yl)ethanone

Conditions	Yield
Stage #1: (E)-2-(((2-styrylphenyl)amino)methyl)phenol; tert.-butyl lithium In tetrahydrofuran; pentane at -25℃; for 1h; Stage #2: 2,2-diethoxypropanenitrile In tetrahydrofuran; pentane at -25℃; for 2h; Stage #3: With hydrogenchloride In tetrahydrofuran; pentane at 20℃; for 0.5h; Further stages.;	50%

methyl coumalate (6018-41-3) + 2,2-diethoxypropanenitrile (56011-12-2) → methyl 4-ethoxybenzoate (23676-08-6)

Conditions	Yield
In toluene at 200℃; for 16h;	48%

n-butyllithium (109-72-8, 29786-93-4) + 2,2-diethoxypropanenitrile (56011-12-2) + (2-vinylphenyl)carbamic acid tert-butyl ester (442850-92-2) → 1-(3-pentyl-1H-indol-2-yl)-ethanone

Conditions	Yield
Stage #1: n-butyllithium; (2-vinylphenyl)carbamic acid tert-butyl ester With N,N,N,N,-tetramethylethylenediamine In diethyl ether; pentane at -78 - -25℃; for 2h; Stage #2: 2,2-diethoxypropanenitrile In diethyl ether; pentane at -78 - -25℃; Stage #3: With hydrogenchloride In water; ethyl acetate at 20℃; for 16h;	44%

2,2-diethoxypropanenitrile (56011-12-2) + tert.-butyl lithium (594-19-4) + 2,2-dimethyl-N-(3-vinyl-pyridin-2-yl)-propionamide (850014-31-2) → 1-[3-(2,2-dimethyl-propyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-ethanone

Conditions	Yield
Multistep reaction.;	44%

2,2-diethoxypropanenitrile (56011-12-2) + tert.-butyl lithium (594-19-4) + N-benzyl-2-vinylbenzylamine (210536-20-2) → 1-benzyl-3-(2,2-dimethylpropyl)-2-acetyl-1H-indole

Conditions	Yield
Stage #1: tert.-butyl lithium; N-benzyl-2-vinylbenzylamine In diethyl ether; hexane at -78℃; for 1h; Stage #2: 2,2-diethoxypropanenitrile In diethyl ether; hexane at -78 - -25℃; Stage #3: With hydrogenchloride In water; ethyl acetate at 20℃; for 16h;	36%

2(R,S)-aminopropanethiol (10229-29-5) + 2,2-diethoxypropanenitrile (56011-12-2) → 2-(1,1-diethoxy-ethyl)-4-methyl-4,5-dihydro-thiazole (37112-86-0)

Conditions	Yield
With ammonium acetate In methanol

1-amino-2-propanethiol (598-36-7) + 2,2-diethoxypropanenitrile (56011-12-2) → 2-(1,1-diethoxy-ethyl)-5-methyl-4,5-dihydro-thiazole (37112-87-1)

Conditions	Yield
With ammonium acetate In methanol

2,4-dithiapentane (1618-26-4) + 2,2-diethoxypropanenitrile (56011-12-2) → 1,1-bis-methylsulfanyl-butane-2,3-dione (56011-19-9)

Conditions	Yield
(i) nBuLi, (ii) /BRN= 1754253/; Multistep reaction;

2,2-diethoxypropanenitrile (56011-12-2) + 1-amino-pentane-2-thiol (64283-04-1) → 2-(1,1-diethoxy-ethyl)-5-propyl-4,5-dihydro-thiazole (37112-88-2)

Conditions	Yield
With ammonium acetate In methanol

2,2-diethoxypropanenitrile (56011-12-2) + Cysteamine (60-23-1) → 2-(1,1-diethoxy-ethyl)-4,5-dihydro-thiazole (29926-40-7)

Conditions	Yield
With ammonium acetate

n-butyllithium (109-72-8, 29786-93-4) + 2,2-diethoxypropanenitrile (56011-12-2) + (2-vinylphenyl)carbamic acid tert-butyl ester (442850-92-2) → 2-(1,1-diethoxy-ethyl)-3-pentyl-indole-1-carboxylic acid tert-butyl ester

Conditions	Yield
Stage #1: n-butyllithium; (2-vinylphenyl)carbamic acid tert-butyl ester With N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at -78 - -25℃; for 2h; Stage #2: 2,2-diethoxypropanenitrile In diethyl ether; hexane at -78 - -25℃; for 3h; Stage #3: With hydrogenchloride In diethyl ether; hexane at -78 - 20℃;

(E)-benzyl-(2-propenylphenyl)amine (909726-02-9) + n-butyllithium (109-72-8, 29786-93-4) + 2,2-diethoxypropanenitrile (56011-12-2) → (+)-1-[1-benzyl-3-(1-methylpentyl)-1H-indol-2-yl]ethanone + (-)-1-[1-benzyl-3-(1-methylpentyl)-1H-indol-2-yl]ethanone

Conditions	Yield
Stage #1: benzyl[2-(propen-1-yl)phenyl]amine With phenyllithium In dibutyl ether at 20℃; for 0.25h; Stage #2: n-butyllithium With (-)-sparteine In hexane; dibutyl ether at -15℃; for 4h; Stage #3: 2,2-diethoxypropanenitrile In hexane; dibutyl ether at 20℃; for 3h; Title compound not separated from byproducts;

2,2-diethoxypropanenitrile (56011-12-2) → N-(2,2-Bisethoxypropionyl)cysteamin (37101-15-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH4OAc 2: aq. H2SO4 View Scheme

(E)-benzyl-(2-propenylphenyl)amine (909726-02-9) + n-butyllithium (109-72-8, 29786-93-4) + 2,2-diethoxypropanenitrile (56011-12-2) → 1-[1-benzyl-3-(1-methylpentyl)-1H-indol-2-yl]ethanone + 1-[1-benzyl-3-(1-methylpentyl)-1H-indol-2-yl]ethanone (909726-11-0)

Conditions	Yield
Multistep reaction. Title compound not separated from byproducts.;

(E)-benzyl-(2-propenylphenyl)amine (909726-02-9) + n-butyllithium (109-72-8, 29786-93-4) + 2,2-diethoxypropanenitrile (56011-12-2) → 1-[1-benzyl-3-(1-methylpentyl)-1H-indol-2-yl]ethanone

Conditions	Yield
Multistep reaction.;

(E)-benzyl-(4-fluoro-2-propenylphenyl)amine (1016170-28-7) + 2,2-diethoxypropanenitrile (56011-12-2) + n-hexyllithium (21369-64-2) → 1-[1-benzyl-5-fluoro-3-(1-methylheptyl)-1H-indol-2-yl]ethanone + 1-[1-benzyl-5-fluoro-3-(1-methylheptyl)-1H-indol-2-yl]ethanone (1016170-41-4)

Conditions	Yield
Multistep reaction. Title compound not separated from byproducts.;

(E)-benzyl-(4-fluoro-2-propenylphenyl)amine (1016170-28-7) + 2,2-diethoxypropanenitrile (56011-12-2) + n-hexyllithium (21369-64-2) → 1-[1-benzyl-5-fluoro-3-(1-methylheptyl)-1H-indol-2-yl]ethanone

Conditions	Yield
Multistep reaction.;

2,2-diethoxypropanenitrile (56011-12-2) → 3-(1,1-diethoxyethyl)-5-methyl-1,2,4-oxadiazole (1202769-30-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium carbonate / methanol; water / 17 h / Reflux 2: 4 h / Reflux View Scheme

2,2-diethoxypropanenitrile (56011-12-2) + (2R)-2-methyl-L-cysteine hydrochloride → C11H19NO4S

Conditions	Yield
With sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 0 - 23℃; pH=8;

2,2-diethoxypropanenitrile (56011-12-2) → C28H46N2O9S

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / N,N-dimethyl-formamide; water / 0 - 23 °C / pH 8 2: N-ethyl-N,N-diisopropylamine; HATU; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 23 °C 3: potassium carbonate / acetone / 24 h / 23 °C View Scheme

2,2-diethoxypropanenitrile (56011-12-2) → C28H45N3O8S

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / N,N-dimethyl-formamide; water / 0 - 23 °C / pH 8 2: N-ethyl-N,N-diisopropylamine; HATU; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 23 °C 3: potassium carbonate / acetone / 24 h / 23 °C View Scheme

2,2-diethoxypropanenitrile (56011-12-2) → C20H30N2O6S

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / N,N-dimethyl-formamide; water / 4 h / 0 - 23 °C / pH 8 2: N-ethyl-N,N-diisopropylamine; HATU; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 23 °C View Scheme

2,2-diethoxypropanenitrile (56011-12-2) → C20H30N2O5S

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / N,N-dimethyl-formamide; water / 0 - 23 °C / pH 8 2: N-ethyl-N,N-diisopropylamine; HATU; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 15 h / 23 °C View Scheme

Upstream product

• 74-90-8 hydrogen cyanide 
• 78-39-7 Triethyl orthoacetate 
• 7677-24-9 trimethylsilyl cyanide 
• 87271-69-0 2-ethoxy-3-bromo-propionitrile 
• 19479-65-3 2-ethoxyacrylonitrile 
• 64-17-5 ethanol 

Downstream Products

• 23676-08-6 methyl 4-ethoxybenzoate 
• 1016170-41-4 1-[1-benzyl-5-fluoro-3-(1-methylheptyl)-1H-indol-2-yl]ethanone 
• 909726-11-0 1-[1-benzyl-3-(1-methylpentyl)-1H-indol-2-yl]ethanone 

Relevant articles and documents

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