20120-21-2

Basic information

• Product Name: 3-DIETHYLAMINOPROPIONIC ACID ETHYL ESTER
• Synonyms: ETHYL BETA-DIETHYLAMINO PROPIONATE;ETHYL 3-DIMETHYLAMINOPROPIONATE;ETHYL 3-(DIETHYLAMINO)PROPANOATE;ETHYL 3-DIETHYLAMINOPROPIONATE;N,N-DIETHYL-BETA-ALANINE ETHYL ESTER;N,N-DIMETHYL-BETA-ALANINE ETHYL ESTER;ethyl N,N-dimethyl-beta-alaninate;3-dimethylaminopropionate
• CAS NO: 20120-21-2
• Molecular Formula: C₇H₁₅NO₂
• Molecular Weight: 173.25
• EINECS: 243-524-7
• Mol File: 20120-21-2.mol

Chemical Properties

• Boiling Point: 56-57°C 12mm
• Flash Point: 58°C
• Appearance: /
• Density: 0,915 g/cm3
• Vapor Pressure: 0.148mmHg at 25°C
• Refractive Index: 1.4190
• PKA: 8.83±0.28(Predicted)
• Water Solubility: Immiscible with water.
• BRN: 1702477
• CAS DataBase Reference: 3-DIETHYLAMINOPROPIONIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-DIETHYLAMINOPROPIONIC ACID ETHYL ESTER(20120-21-2)
• EPA Substance Registry System: 3-DIETHYLAMINOPROPIONIC ACID ETHYL ESTER(20120-21-2)

Safety Data

• Statements: 36/37/38-10
• Safety Statements: 26-36
• RIDADR: 1993
• RTECS: AY5992700
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 20120-21-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-DIETHYLAMINOPROPIONIC ACID ETHYL ESTER is used as an intermediate compound for the synthesis of [3-(dimethylamino)propionyl]guanidine. This synthesized compound has potential applications in the development of pharmaceuticals, particularly those targeting cardiovascular and neurological disorders. The ester group in Ethyl 3-dimethylaminopropionate allows for further chemical modifications and functionalization, making it a versatile building block in the synthesis of various drug candidates.

InChI:InChI=1/C9H19NO2/c1-4-10(5-2)8-7-9(11)12-6-3/h4-8H2,1-3H3

Upstream product

• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 
• 927-80-0 1-ethoxyacetylene 
• 140-88-5 ethyl acrylate 
• 56275-84-4 N-(butoxymethyl)dimethylamine 
• 65946-52-3 1-Ethoxy-1-trimethylsilyloxy-1-buten 
• 539-74-2 Ethyl 3-bromopropionate 
• 50283-25-5 catechol diacrylate 
• 7732-18-5 water 
• 92-84-2 10H-phenothiazine 
• 150-76-5 4-methoxy-phenol 
• 3586-58-1 2-methylenebutyric acid 

Downstream Products

• 4320-42-7 3-dimethylamino-1,1-diphenyl-propan-1-ol 
• 130515-23-0 methyl 2-(dimethylamino)propanoate ? 
• 25363-28-4 1-(Dimethylaminoethyl)-cyclohexanol-⁽¹⁾ 
• 22636-79-9 3-(dimethylamino)propanehydrazide 
• 85594-19-0 3-Dimethylammonio-propionylhydroxamsaeure 
• 3699-67-0 ethyl 3-(diethoxyphosphoryl)propanoate 
• 145398-27-2 Toluene-4-sulfonate(2-ethoxycarbonyl-ethyl)-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-2-hydroxy-decyl)-dimethyl-ammonium; 
• 19075-26-4 ethyl (trimethylammonio)propionate iodide 
• 23577-37-9 2-Benzyl-4-dimethylamino-1-phenylbutan-2-ol 
• 2409-52-1 diethylitaconate 
• 90696-19-8 cis-3-((dimethylamino)methyl)-4-phenyl-2-azetidinone 
• 4646-55-3 N,N-dimethyl-3,3-diphenylpropan-1-amine 
• 23690-05-3 (3,3-diphenyl-allyl)-dimethyl-amine 
• 69311-00-8 (3,3-diphenyl-allyl)-trimethyl-ammonium; iodide 

Relevant articles and documents

MANUFACTURING METHOD OF N-SUBSTITUTED (METH)ACRYLAMIDE

To provide a method for industrially manufacturing high purity β-alkoxypropionic acid amide, β-aminopropionic acid amide and N-substituted (meth)acrylamide at high yield using (meth)acrylic acid ester as a starting material.SOLUTION: By conducting an amidation reaction with amine in the presence of a metal complex as a catalyst using β-substituted propionic acid ester which is a product material of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine, β-substituted propionic acid amide is obtained. Further by conducting a thermal decomposition reaction of the β-substituted propionic acid amide in the presence of the metal complex, and eliminating the alcohol or the amine, objective compound N-substituted (meth)acrylamide is obtained.SELECTED DRAWING: None

MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE

PROBLEM TO BE SOLVED: To provide a method for industrially manufacturing β-alkoxy propionic acid amide, β-amino propionic acid amide and N-substituted (meth)acryl amide using (meth)acrylic acid ester as starting material at high yield and high purity. SOLUTION: There is provided a method for obtaining N-substituted (meth)acryl amide represented by target compound formula (7) by conducting an amidation reaction with amine using β-substituted propionic acid ester represented by the formula (1) of a product of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine in presence of a metal complex as a catalyst to obtain β-substituted propionic acid amide represented by the formula (3) and conducting a thermal decomposition reaction of β-substituted propionic acid amide in presence of the metal complex as the catalyst to eliminate alcohol or amine. A-CH2-C(R1)H-C(=O)-OR2 (1), A-CH2-C(R1)H-C(=O)-N(R3)R4 (3), CH2=C(R1)-C(=O)-N(R3)R4 (7) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Cesium fluoride catalyzed Aza-Michael addition reaction in aqueous media

A green approach to the Aza-Michael addition reaction between an amine and α,β-unsaturated compounds has been achieved by conventional as well as non-conventional methods. The reaction is catalyzed by cesium fluoride (CsF) in aqueous media at ambient temperature to afford the product in excellent yield. Ultrasound irradiation has been used as a non-conventional energy source, which reduces the reaction time with improved product yield.

Highly efficient procedure for the conjugate addition of amines to electron deficient alkenes

The novel efficient procedure has been developed for the conjugate addition of amines to electron deficient alkenes. The results showed that the catalyst was very efficient for the reactions with the excellent yields in several minutes. Operational simplicity, without need of any solvent, low cost of the catalyst used, high yields, reusability, excellent chemoselectivity, applicability to large-scale reactions are the key features of this methodology. The article is published in the original.

N-donor ligand as catalyst: A simple Aza-Michael addition reaction in aqueous media

(Chemical Equation Presented) A novel approach for the Aza-Michael addition reactions between various amines and α,β-unsaturated esters, nitriles and ketones using N-donor Ligand catalyst (3 mol %) is described. The reactions are carried out in aqueous media at an ambient temperature to afford the products in excellent yields.

Addition of secondary amines to α,β-unsaturated carbonyl compounds and nitrites by using microstructured reactors

Several additions of amines to α,β-unsaturated carbonyl compounds (Michael additions) were performed in a continuous-flow microstructured reactor rig and compared to the respective batch reaction. Dimethylamine/diethylamine/piperidine and acrylic acid ethyl ester/acrylonitrile were employed as two sets of reactants, giving six reactions. Some of these reactions are highly exothermal. Using the traditional batch procedure the olefin must be added quite slowly to the diluted amine to ensure temperature control and safe operation; especially this is necessary for the addition of dimethylamine (40 mass % aqueous solution) to acrylonitrile. Good yields (>85%) are achieved in this way; however, processing time is very long (17-25 h). To reveal the intrinsic kinetic potential and thus to accelerate these reactions, the reactants were mixed in a continuous-flow microstructured reactor rig which allows rapid mixing and efficient removal of the reaction heat. In this way, reaction time was decreased to a few seconds up to about half an hour, which is a change by 2 orders of magnitude. While the yields achieved with the continuous-flow microstructured reactor rig matched those for the batch procedure, the space-time yields for the microflow processing are much higher, in the best case by a factor of about 650.

Reaction of Thioaldehydes with Amines

The reaction of phosphonium ylides with elemental sulfur gave thioaldehydes, which changed to the corresponding thioamides in good yields when treated with amines.When thioaldehydes containing α-hydrogens were treated with secondary amines, the corresponding enamines or reduction products were obtained.

Intercharge Distance of Flexible Zwitterionic Molecules in Solution

The conformation of flexible zwitterionic molecules in solutions of polar solvents is studied by means of a NMR chemical shift method.This method makes use of chemical shift changes of NMR lines, induced by the electrostatic field caused by the electrical charges of the zwitterion.The electrostatic field at the observed nucleus is calculated, taking distances of zwitterionic (trimethylammonio)alkanoates in aqueous and methanolic solutions are then deduced from the 13C NMR chemical shift data as a function of the number of methylenes linking the cationic and anionic groups of the zwitterion.The comparison of experimental data with the end to end distances predicted by the rotational isomerism state theory shows that the polymethylene chain has a more folded conformation than the free chain.Electrostatic attraction between the two zwitterionic charges is thus important, although it could be expected that it could be offset by steric hindrance, i.e., by the bulkiness of terminal charged groups.

N-Trimethylsilyl Imines: Applications to the Synthesis of β-Lactams

Ester enolates and N-trimethylsilyl imines react to afford N-protio-β-lactams.The stereochemical course of the reaction depends on the ester enolate geometry.Therefore (E)-enolates give mainly cis β-lactams while (Z)-enolates give nearly equal mixtures of cis and trans β-lactams.The use of ethyl β-hydroxybutyrate as the ester component allows the preparation of β-lactams of potential use in carbapenem synthesis.The differences in the behavior of N-trimethylsilyl and N-aryl imines in ester-imine condensations are also discussed.

REACTIONS OF α-HETEROATOM-SUBSTITUTED ETHERS AND SULFIDES WITH SILYL ENOL ETHERS. CHEMOSELECTIVITY IN THE CLEAVAGE OF HETEROATOM-CARBON BONDS BY IODOTRIMETHYLSILANE AND TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE

Reactions of α-heteroatom substituted ethers and related compounds (R1R2CXY; X, Y = RO, RS and Cl) with silyl enol ethers and ketene silyl acetals took place in the presence of iodotrimethylsilane (Ia) and trimethylsilyl triflate (Ib) as a catalyst and factors influencing the activation of the heteroatom by I were examined.