2032-34-0

Basic information

• Product Name: 3,3-Diethoxypropionitrile
• Synonyms: CYANOACETALDEHYDE DIETHYL ACETAL;CYADEA;1,1-DIETHOXY-2-CYANOETHANE;3,3-DIETHOXYPROPIONITRILE;2-CYANOACETALDEHYDE DIETHYLACETAL;3,3-diethoxypropiononitrile;Propanenitrile, 3,3-diethoxy-;3,3-Diethoxypropiononitril
• CAS NO: 2032-34-0
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.18
• EINECS: 217-988-6
• Product Categories: C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;NULL
• Mol File: 2032-34-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 82-84
• Boiling Point: 91-93 °C11 mm Hg(lit.)
• Flash Point: 183 °F
• Appearance: Clear yellow to brownish liquid
• Density: 0.954 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0508mmHg at 25°C
• Refractive Index: n20/D 1.415(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 32g/l
• CAS DataBase Reference: 3,3-Diethoxypropionitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-Diethoxypropionitrile(2032-34-0)
• EPA Substance Registry System: 3,3-Diethoxypropionitrile(2032-34-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 3275
• WGK Germany: 2
• Hazardous Substances Data: 2032-34-0(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR YELLOW TO BROWNISH LIQUID

Uses

Different sources of media describe the Uses of 2032-34-0 differently. You can refer to the following data:
1. 3,3-Diethoxypropionitrile is a propionitrile derivative used in the preparation of various biologically active compounds such as p38α mitogen-activated protein kinase inhibitors.
2. 3,3-Diethoxypropionitrile may be used in the synthesis of 2-(2,2-diethoxy-ethyl)-pyridine, via [2+2+2]-cycloaddition reaction. It may be used in the synthesis of cyanomalondialdehyde.

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 2657, 1947 DOI: 10.1021/ja01203a028

General Description

3,3-Diethoxypropionitrile is a cyanide derivative. It undergoes reaction with urea in refluxing butanolic sodium butoxide to afford 4-amino-2(1H)-pyrimidinone and cytosine. Its physical properties (density, refractive index, boiling point and melting point) have been reported.

InChI:InChI=1/C7H13NO2/c1-3-9-7(5-6-8)10-4-2/h7H,3-5H2,1-2H3

Synthetic route

ISOXAZOLE (288-14-2) + diethyl sulfate (64-67-5) → 3-ethoxyacrylonitrile (61310-53-0) + 3,3-bis(ethyloxy)propanenitrile (2032-34-0)

Conditions	Yield
With sodium hydroxide; ethanol

propiolonitrile (1070-71-9) + sodium ethanolate (141-52-6) → 3,3-bis(ethyloxy)propanenitrile (2032-34-0)

Conditions	Yield
With ethanol

3-ethoxyacrylonitrile (61310-53-0) + sodium ethanolate (141-52-6) → 3,3-bis(ethyloxy)propanenitrile (2032-34-0)

3,3-diethoxypropionic amide (41365-74-6) → 3-ethoxyacrylonitrile (61310-53-0) + 3,3-bis(ethyloxy)propanenitrile (2032-34-0)

Conditions	Yield
With phosphorus pentoxide; triethylamine; benzene

potassium cyanide (151-50-8) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 3,3-bis(ethyloxy)propanenitrile (2032-34-0)

Conditions	Yield
With ethanol; sodium iodide

sodium ethanolate (141-52-6) + trans-β-chloroacrylonitrile (871-29-4, 3721-37-7, 3721-38-8) → 3,3-bis(ethyloxy)propanenitrile (2032-34-0)

Conditions	Yield
In ethanol

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + methyl 5-acetamido-2-amino-4-ethoxybenzoate (1222172-49-7) → methyl 5-acetamido-2-[(2-cyanovinyl)amino]-4-ethoxybenzoate (1222172-50-0)

Conditions	Yield
Stage #1: 3,3-bis(ethyloxy)propanenitrile With water; trifluoroacetic acid at 20℃; for 12h; Stage #2: methyl 5-acetamido-2-amino-4-ethoxybenzoate In ethyl acetate at 20℃; Product distribution / selectivity;	96%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + ethyl 5-acetamido-2-amino-4-ethoxybenzoate (1222172-51-1) → ethyl 2-[(2-cyanovinyl)amino]-4-ethoxy-5-acetylamidobenzoate (1222172-52-2)

Conditions	Yield
Stage #1: 3,3-bis(ethyloxy)propanenitrile With water; trifluoroacetic acid at 20℃; for 9h; Stage #2: ethyl 5-acetamido-2-amino-4-ethoxybenzoate In ethyl acetate at 20℃; for 12h;	90.6%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + ethyl 5-amino-1H-pyrazole-4-carboxylate (1260243-04-6, 6994-25-8) → ethyl 7-aminopyrazolo[1,5-a]pyrimidine-3-carboxylate

Conditions	Yield
With hydrogenchloride In 1,4-dioxane Reflux;	88%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + acetylene (74-86-2) → 2-(2,2-diethoxyethyl)pyridine (91340-40-8)

Conditions	Yield
(η5-cyclopentadienyl)-η4-cycloocta-1,5-dienecobalt(I) In toluene at 25℃; for 4h; Irradiation;	87%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 5-amino-3-methylthio-1,2,4-triazole (45534-08-5) → 5-Amino-2-methylthio-1,2,4-triazolo<1,5-a>pyrimidine (113967-74-1)

Conditions	Yield
Stage #1: 3,3-bis(ethyloxy)propanenitrile; 5-amino-3-methylthio-1,2,4-triazole With hydrogenchloride In 1,4-dioxane Reflux; Stage #2: With potassium hydroxide In ethanol; water at 40℃; Dimroth Rearrangement;	86%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 2-Amino-4-(3-chloro-propoxy)-5-methoxy-benzoic acid methyl ester (214470-59-4) → methyl (E)-4-(3-chloropropoxy)-2-(2-cyanovinylamino)-5-methoxybenzoate (1248588-02-4)

Conditions	Yield
Stage #1: 3,3-bis(ethyloxy)propanenitrile With water; trifluoroacetic acid at 5 - 10℃; for 6h; Inert atmosphere; Stage #2: 2-Amino-4-(3-chloro-propoxy)-5-methoxy-benzoic acid methyl ester In water; ethyl acetate for 0.166667h; Inert atmosphere;	84.3%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 3-(thiophen-2-yl)-1H-1,2,4-triazol-5-amine (4922-99-0) → 2-(thiophen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Conditions	Yield
With hydrogenchloride In 1,4-dioxane Reflux;	83%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + (2E)-4-(1,3-Benzodithiol-2-yliden)but-2-enal (181296-27-5) → (2E,4E)-6-Benzo[1,3]dithiol-2-ylidene-2-formyl-hexa-2,4-dienenitrile

Conditions	Yield
With sodium methylate In tetrahydrofuran for 24h; Ambient temperature;	81%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 2-amino-4-bromobenzaldehyde (59278-65-8) → 7-bromo-3-quinolinecarbonitrile (1375108-40-9)

Conditions	Yield
With p-toluenesulfonic acid monohydrate In toluene for 3h; Reflux;	75%
With toluene-4-sulfonic acid In toluene for 3h; Dean-Stark; Reflux;	75%
With toluene-4-sulfonic acid In toluene for 3h; Reflux;	75%
With toluene-4-sulfonic acid In toluene for 3h; Reflux; Dean-Stark;	75%

Methyl formate (107-31-3) + 3,3-bis(ethyloxy)propanenitrile (2032-34-0) → 3,3-diethoxy-2-formylpropionitrile potassium salt

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; hexane at 10 - 20℃; for 3.08h;	73%
With potassium tert-butylate In tetrahydrofuran; hexane
With potassium tert-butylate In tetrahydrofuran; hexane

Methyl formate (107-31-3) + 3,3-bis(ethyloxy)propanenitrile (2032-34-0) → 1,3-diethoxy-2-formylpropionitrile potassium salt (449811-60-3)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 10 - 20℃; for 2.75h;	73%
With potassium tert-butylate In tetrahydrofuran at 10 - 20℃; for 2.75h;
With potassium tert-butylate In tetrahydrofuran at 10 - 20℃; for 2.075h;

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 3-amino-1,2,4-triazole (61-82-5) → 7-amine-1,2,4-triazolo[1,5-a]pyrimidine (5915-16-2) + [1,2,4]triazolo[4,3-a]pyrimidin-5-amine

Conditions	Yield
With hydrogenchloride In ethanol; water Reflux;	A n/a B 72%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 3-amino-1,2,4-triazole (61-82-5) → 7-amine-1,2,4-triazolo[1,5-a]pyrimidine (5915-16-2)

Conditions	Yield
Stage #1: 3,3-bis(ethyloxy)propanenitrile; 3-amino-1,2,4-triazole With hydrogenchloride In ethanol for 3h; Reflux; Stage #2: With potassium hydroxide In ethanol; water at 20℃; Dimroth Rearrangement;	71%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + (E)-4-(4,5-dimethyl-1,3-dithiol-2-ylidene)but-2-enal (181046-74-2) → (2E,4E)-6-(4,5-Dimethyl-[1,3]dithiol-2-ylidene)-2-formyl-hexa-2,4-dienenitrile

Conditions	Yield
With sodium methylate In tetrahydrofuran for 72h; Ambient temperature;	69%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + (2,6-dichlorophenyl)hydrazine monohydrochloride (50709-36-9) → 1-(2,6-dichlorophenyl)-1H-pyrazol-5-amine

Conditions	Yield
In ethanol for 18h; Reflux;	68%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 4-Diethylaminobenzaldehyde (120-21-8) → (E)-3-(4-(diethylamino) phenyl)-2-formylacrylonitrile

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 60℃;	68%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 3-(furan-2-yl)-1H-1,2,4-triazol-5-amine (3663-61-4) → 2-(furan-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Conditions	Yield
With hydrogenchloride In 1,4-dioxane Reflux;	68%

5-aminotetrazole (4418-61-5) + 3,3-bis(ethyloxy)propanenitrile (2032-34-0) → tetrazolo[1,5-a]pyrimidin-7-amine

Conditions	Yield
With hydrogenchloride In 1,4-dioxane Reflux;	67%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 3-amino-5-trifluoromethyl<1,2,4>triazole (25979-00-4) → 2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Conditions	Yield
With hydrogenchloride In 1,4-dioxane Reflux;	65%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + (2,2-diethoxyethyl)-2,4-diphenyl-1H-pyrrole → 1,3-diphenylindolizine-7-carbonitrile

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In acetonitrile at 60℃; for 4h;	65%

2-methyl-3-(trifluoromethyl)benzaldehyde (878001-20-8) + 3,3-bis(ethyloxy)propanenitrile (2032-34-0) → (2E)-2-[bis(methyloxy)methyl]-3-[2-methyl-3-(trifluoromethyl)phenyl]-2-propenenitrile (1420468-43-4)

Conditions	Yield
With sodium methylate In methanol at 20℃;	64%
With sodium methylate In methanol; water; ethyl acetate

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 4-(diphenylamino)benzaldehyde (4181-05-9) → (E)-3-(4-(diphenylamino) phenyl)-2-formylacrylonitrile

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 60℃;	62%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 10-ethyl-10H-phenothiazine-3-carbaldehyde (18413-61-1) → (E)-3-(10-ethyl-10H-phenothiazine-3-yl) 2formylacrylonitrile

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 60℃;	60%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 3-methyl-1H-1,2,4-triazol-5-amine (4923-01-7) → 2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine (1435464-72-4)

Conditions	Yield
Stage #1: 3,3-bis(ethyloxy)propanenitrile; 3-methyl-1H-1,2,4-triazol-5-amine With hydrogenchloride In 1,4-dioxane Reflux; Stage #2: With potassium hydroxide In water at 20℃; Dimroth Rearrangement;	60%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + 7-diethylaminocoumarine-3-aldehyde (57597-64-5) → C17H16N2O3 (1312992-76-9)

Conditions	Yield
With iron(III) chloride hexahydrate; acetic acid In ethanol at 90℃; for 5h;	59.3%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + N-ethyl-3-carbazolealdehyde (7570-45-8) → (E)-3-(9-ethyl-9H-carbazol-3-yl)-2-formylacrylonitrile

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 60℃;	58%

1-amino-1H-pyrrole-2,4-dicarboxylic acid diethyl ester (869066-99-9) + 3,3-bis(ethyloxy)propanenitrile (2032-34-0) → 3-cyano-4-hydroxy-pyrrolo[-1,2-b]pyridazine-6-carboxylic acid ethyl ester (779345-24-3)

Conditions	Yield
Stage #1: 1-amino-1H-pyrrole-2,4-dicarboxylic acid diethyl ester; 3,3-bis(ethyloxy)propanenitrile With toluene-4-sulfonic acid at 125℃; for 3h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20 - 80℃; for 2h;	50%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid In ethanol at 80 - 125℃; for 5h;	50%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) → aminopropane diethyl acetal (41365-75-7)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 16h; Ambient temperature;	49%
With lithium aluminium tetrahydride

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + thiourea (17356-08-0) → 2-thiocytosine (333-49-3)

Conditions	Yield
With sodium In butan-1-ol at 40 - 50℃; for 5h; Inert atmosphere;	48%
With sodium butanolate

ethyl 1-amino-1H-pyrrole-2-carboxylate (628733-99-3) + 3,3-bis(ethyloxy)propanenitrile (2032-34-0) → 4-hydroxypyrrolo[1,2-b]pyridazine-3-carbonitrile (1263419-99-3)

Conditions	Yield
Stage #1: ethyl 1-amino-1H-pyrrole-2-carboxylate; 3,3-bis(ethyloxy)propanenitrile With hydrogenchloride In ethanol; water for 18h; Reflux; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol; water at 80℃; for 1h; Stage #3: With hydrogenchloride In water pH=1;	47%
Stage #1: ethyl 1-amino-1H-pyrrole-2-carboxylate; 3,3-bis(ethyloxy)propanenitrile With hydrogenchloride In ethanol; water for 18h; Reflux; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol; water at 20℃; for 1h; Reflux;	47%

Upstream product

• 141-52-6 sodium ethanolate 
• 871-29-4 trans-β-chloroacrylonitrile 
• 64-67-5 diethyl sulfate 
• 76064-23-8 3-hydroxyacrylonitrile sodium salt 
• 64-17-5 ethanol 
• 107-13-1 acrylonitrile 
• 10601-80-6 ethyl 3,3-diethoxypropanoate 
• 41365-74-6 3,3-diethoxypropionic amide 
• 288-14-2 ISOXAZOLE 
• 143-33-9 sodium cyanide 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 13435-20-6 tetraethylammoniumcyanide 
• 151-50-8 potassium cyanide 
• 61310-53-0 3-ethoxyacrylonitrile 

Downstream Products

• 111599-07-6 (+/-)-1-(cyanomethyl)-1,2,3,4-tetrahydroisoquinoline 
• 64935-37-1 2-propylhept-2-enal 
• 1198476-02-6 5-propyl-3-cyanofuran 
• 56069-64-8 2-Cyano-3-phenylpropenal 
• 1196153-97-5 ethyl 7-aminopyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 113967-74-1 5-Amino-2-methylthio-1,2,4-triazolo<1,5-a>pyrimidine 
• 5915-16-2 7-amino-1,2,4-triazolo[1,5-a]pyrimidine 
• 1420468-43-4 (2E)-2-[bis(methyloxy)methyl]-3-[2-methyl-3-(trifluoromethyl)phenyl]-2-propenenitrile 
• 1375108-40-9 7-bromo-3-quinolinecarbonitrile 
• 1222172-52-2 ethyl 2-[(2-cyanovinyl)amino]-4-ethoxy-5-acetylamidobenzoate 
• 1222172-50-0 methyl 5-acetamido-2-[(2-cyanovinyl)amino]-4-ethoxybenzoate 
• 1248588-02-4 methyl (E)-4-(3-chloropropoxy)-2-(2-cyanovinylamino)-5-methoxybenzoate 
• 71-30-7 Cytosine 

Relevant articles and documents

3 - Ethoxy acrylonitrile and 3, 3 - diethyl dimethoxypropionitrile is treated mixture of synthetic method

The invention belongs to the field of medicinal chemistry, in particular to medicinal chemistry of the in the field of organic synthesis, more in particular to 3 - ethoxy acrylonitrile and 3, 3 - diethyl dimethoxypropionitrile is treated mixture of synthetic method. The method uses acetonitrile with a ester alcohol under the action of the alkali metal salt, to obtain the intermediate compound II, then this compound II and then under the action of the phase transfer catalyst, with the sulfuric acid b b obtained by the target mixture compound I, namely 3 - ethoxy acrylonitrile and 3, 3 - diethyl dimethoxypropionitrile is treated mixture. The invention disclosed 3 - ethoxy acrylonitrile and 3, 3 - diethyl dimethoxypropionitrile is treated mixture of the synthetic method has low material cost, relatively mild reaction conditions, the operation is simple, the yield and the like, which is suitable for the industrial production, application of the method.

Process for producing an acetal

An acetal is produced at a high yield and a high selectivity by contacting an olefin and an alcohol with each other in the presence of (a) a nitrite, (b) a platinum group metal or the salts thereof and (c) a halide at a high reaction rate without requirement of any troublesome operations for the separation, recovery and regeneration of the catalyst.