13894-28-5

Basic information

• Product Name: ethyl (E)-3-diethylaminoprop-2-enoate
• Synonyms: ethyl (E)-3-diethylaminoprop-2-enoate;Ethyl (E)-3-(N,N-diethylamino)propenoate;Ethyl (E)-3-(diethylamino)acrylate
• CAS NO: 13894-28-5
• Molecular Formula: C₉H₁₇NO₂
• Molecular Weight: 171.24
• Mol File: 13894-28-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 227.3°Cat760mmHg
• Flash Point: 80.5°C
• Appearance: /
• Density: 0.943g/cm³
• Vapor Pressure: 0.0781mmHg at 25°C
• Refractive Index: 1.455
• CAS DataBase Reference: ethyl (E)-3-diethylaminoprop-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (E)-3-diethylaminoprop-2-enoate(13894-28-5)
• EPA Substance Registry System: ethyl (E)-3-diethylaminoprop-2-enoate(13894-28-5)

Safety Data

• Hazardous Substances Data: 13894-28-5(Hazardous Substances Data)

Usage

General Description

Ethyl (E)-3-diethylaminoprop-2-enoate, also known as DEAP, is a chemical compound that belongs to the class of esters. It is commonly used as a reagent in organic synthesis for the preparation of various compounds. DEAP is a colorless liquid with a slightly fruity odor, and it is soluble in organic solvents such as ethanol and acetone. It is often used as a flavoring agent in the food and beverage industry and as a fragrance ingredient in cosmetic products. DEAP is also used in the pharmaceutical industry for the synthesis of various drugs and pharmaceutical intermediates. Additionally, it has potential applications in the field of polymer chemistry and materials science due to its ability to polymerize and form complex molecules.

InChI:InChI=1/C9H17NO2/c1-4-10(5-2)8-7-9(11)12-6-3/h7-8H,4-6H2,1-3H3/b8-7+

Synthetic route

ethyl 3-(diethylamino)-3-oxopropanoate (33567-70-3) → ethyl 3-(diethylamino)acrylate (13894-28-5)

Conditions	Yield
With bis(triphenylphosphine)carbonyliridium(I) chloride; 1,1,3,3-Tetramethyldisiloxane In toluene at 20℃; for 1h; Inert atmosphere; chemoselective reaction;	92%

diethylamine (109-89-7) + propynoic acid ethyl ester (623-47-2) → ethyl 3-(diethylamino)acrylate (13894-28-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; (E)-1-bromo-2-iodoethylene In tetrahydrofuran at 23℃; for 12h;	92%
With benzene
In ethanol
In ethanol	29.83 g (87 %)

N,N-diethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-amine (791785-35-8) + propynoic acid ethyl ester (623-47-2) → ethyl 3-(diethylamino)acrylate (13894-28-5)

Conditions	Yield
With sodium t-butanolate; tricyclohexylphosphine In methanol at 70℃; for 17h; Inert atmosphere; Schlenk technique;	93%

triethylamine (121-44-8) + propynoic acid ethyl ester (623-47-2) → ethyl 3-(diethylamino)acrylate (13894-28-5)

Conditions	Yield
With zinc dibromide In acetonitrile at 50 - 60℃; for 13h;	53%

ethyl 3-(trimethylsilyl)propynoate (16205-84-8) + diethylamine (109-89-7) → ethyl 3-(diethylamino)acrylate (13894-28-5)

Conditions	Yield
In diethyl ether for 4h;	34%

(E)-1,1,1-Trichloro-4-(N,N-diethylamino)but-3-en-2-one (24960-56-3) + sodium ethanolate (141-52-6) → ethyl 3-(diethylamino)acrylate (13894-28-5)

Conditions	Yield
In ethanol	95%
In ethanol Product distribution;	95%

C9H17NO2 (54299-82-0) → ethyl 3-(diethylamino)acrylate (13894-28-5)

Conditions	Yield
at 130 - 175℃;

diethylamine (109-89-7) + propynoic acid ethyl ester (623-47-2) + benzene (71-43-2) → ethyl 3-(diethylamino)acrylate (13894-28-5)

Conditions	Yield
reagiert analog mit Anilin und Piperidin;

ethyl 3-(diethylamino)acrylate (13894-28-5) + (Z)-1-bromo-1-heptene (39924-57-7) → ethyl 2,4-decadienoate (3025-30-7, 3025-31-8, 7328-34-9, 37549-74-9, 123474-79-3, 136707-82-9)

Conditions	Yield
(i) Li, Et2O, (ii) /BRN= 2083336/; Multistep reaction;

3-ethyl-2,4,5-trifluoro-benzoyl chloride + ethyl 3-(diethylamino)acrylate (13894-28-5) → ethyl α(E)-[(diethylamino)methylene]-3-ethyl-2,4,5-trifluoro-β-oxo-benzenepropanoate (925457-03-0)

Conditions	Yield
With triethylamine In toluene at 90℃; for 5h;	750 mg

ethyl 3-(diethylamino)acrylate (13894-28-5) + 2,4,5-trifluoro-3-methoxybenzoyl chloride (112811-66-2) → ethyl α(E)-[(diethylamino)methylene]-2,4,5-trifluoro-3-methoxy-β-oxo-benzenepropanoate (925457-02-9)

Conditions	Yield
With triethylamine In toluene at 90℃; for 5h;	1.88 g

ethyl 3-(diethylamino)acrylate (13894-28-5) + 2,4-dichloro-5-fluorobenzoyl chloride (86393-34-2) → ethyl 3-diethylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylate

Conditions	Yield
With triethylamine In 1,4-dioxane; dichloromethane; water

ethyl 3-(diethylamino)acrylate (13894-28-5) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → ethyl 2-[[(2,2,2-trichloroethoxycarbonyl)amino]thioxomethyl]-3-(diethylamino)-propenoate

Conditions	Yield
18-crown-6 ether In toluene	30 g (74 %)

ethyl 3-(diethylamino)acrylate (13894-28-5) → ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylate (98349-25-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / toluene / 18 h / 90 °C 2.1: ethanol; diethyl ether / 3 h / 20 °C 2.2: 16 h / 100 °C View Scheme

ethyl 3-(diethylamino)acrylate (13894-28-5) → 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate ethyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / toluene / 18 h / 90 °C 2.1: ethanol; diethyl ether / 3 h / 20 °C 2.2: 16 h / 100 °C 3.1: acetonitrile / Reflux View Scheme

ethyl 3-(diethylamino)acrylate (13894-28-5) → ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (112811-71-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / toluene / 5 h / 90 °C 2.1: ethanol; diethyl ether / 3 h / 20 °C 2.2: 5 h / 100 °C View Scheme

ethyl 3-(diethylamino)acrylate (13894-28-5) → 1-cyclopropyl-6-fluoro-4-oxo-7-(4-pentylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate ethyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / toluene / 18 h / 90 °C 2.1: ethanol; diethyl ether / 3 h / 20 °C 2.2: 16 h / 100 °C 3.1: acetonitrile / Reflux 4.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 20 h / 20 °C View Scheme

ethyl 3-(diethylamino)acrylate (13894-28-5) + 2,4,5-trifluorobenzoyl chloride (88419-56-1) → ethyl α(Z)-[(diethylamino)methylene]-2,4,5-trifluoro-β-oxo-benzenepropanoate

Conditions	Yield
With triethylamine In toluene at 90℃; for 18h;	4.18 g

ethyl 3-(diethylamino)acrylate (13894-28-5) + 2,4,5-trifluoro-3-methoxybenzoyl chloride (112811-66-2) → ethyl α(Z)-[(diethylamino)methylene]-2,4,5-trifluoro-3-methoxy-β-oxo-benzenepropanoate

Conditions	Yield
With triethylamine In toluene at 90℃; for 5h;	1.88 g

Upstream product

• 109-89-7 diethylamine 
• 623-47-2 propynoic acid ethyl ester 
• 71-43-2 benzene 
• 16205-84-8 ethyl 3-(trimethylsilyl)propynoate 
• 121-44-8 triethylamine 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 33567-70-3 ethyl 3-(diethylamino)-3-oxopropanoate 
• 791785-35-8 N,N-diethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-amine 
• 24960-56-3 (E)-1,1,1-Trichloro-4-(N,N-diethylamino)but-3-en-2-one 
• 141-52-6 sodium ethanolate 
• 54299-82-0 C₉H₁₇NO₂ 

Downstream Products

• 112811-71-9 ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate 
• 105404-65-7 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate ethyl ester 
• 98349-25-8 ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylate 
• 3025-30-7 ethyl 2,4-decadienoate 
• 925457-02-9 ethyl α(E)-[(diethylamino)methylene]-2,4,5-trifluoro-3-methoxy-β-oxo-benzenepropanoate 
• 925457-03-0 ethyl α(E)-[(diethylamino)methylene]-3-ethyl-2,4,5-trifluoro-β-oxo-benzenepropanoate 

Relevant articles and documents

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