623-72-3

Basic information

• Product Name: propanoic acid, 3-hydroxy-, ethyl ester
• Synonyms: ethyl 3-hydroxypropanoate;propanoic acid, 3-hydroxy-, ethyl ester;ethyl 3-hydroxypropanoate(SALTDATA: FREE);3-hydroxypropanoic acid ethyl ester
• CAS NO: 623-72-3
• Molecular Formula: C₅H₁₀O₃
• Molecular Weight: 118.1311
• Mol File: 623-72-3.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 187.5°C (estimate)
• Flash Point: 79.075°C
• Appearance: /
• Density: 1.054
• Vapor Pressure: 0.175mmHg at 25°C
• Refractive Index: 1.423
• Storage Temp.: 2-8°C
• PKA: 14.39±0.10(Predicted)
• CAS DataBase Reference: propanoic acid, 3-hydroxy-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: propanoic acid, 3-hydroxy-, ethyl ester(623-72-3)
• EPA Substance Registry System: propanoic acid, 3-hydroxy-, ethyl ester(623-72-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 623-72-3(Hazardous Substances Data)

Usage

General Description

Propanoic acid, 3-hydroxy-, ethyl ester, also known as ethyl 3-hydroxypropanoate, is a chemical compound with the molecular formula C5H10O3. It is commonly used as a flavoring agent and food additive, adding a sweet, fruity aroma to various products. It is also used as a precursor for the synthesis of pharmaceuticals and other organic compounds. Ethyl 3-hydroxypropanoate is also used in the production of perfumes and fragrances due to its pleasant odor. Additionally, it has potential applications in the production of polymers and plastics, as well as in the production of solvents and cleaning agents.

InChI:InChI=1/C5H10O3/c1-2-8-5(7)3-4-6/h6H,2-4H2,1H3

Synthetic route

Ethyl 3-bromopropionate (539-74-2) → ethyl 3-hydroxypropanoate (623-72-3) + ethyl acrylate (140-88-5)

Conditions	Yield
With oxygen; tetraethylammonium perchlorate In N,N-dimethyl-formamide at 20℃; electroreduction at -1.1 V;	A 70% B 20 % Chromat.
With oxygen In N,N-dimethyl-formamide at 20℃; Product distribution; electrolysis of the oxygen saturated solution at -1,1 V; 0.1 M TEAP; further esters;	A 70% B 20 % Chromat.

ethanol (64-17-5) + 3-hydroxypropionic acid (503-66-2) → ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
With sulfuric acid at 78 - 80℃; under 760.051 Torr; for 10h; Time;	67.24%
With copper(II) sulfate
amberlyst-15 at 20℃; for 19h; Product distribution / selectivity;	17 - 68 %Chromat.
Nafion NR-50 at 20℃; for 21h; Product distribution / selectivity;	71 %Chromat.

ethanol (64-17-5) + 3-ethoxy-1,2-dioxolane (97674-27-6) → ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
With Amberlyst 15	66%

ethanol (64-17-5) + 3-Hydroxypropionitrile (109-78-4) → ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
With hydrogenchloride; thionyl chloride In water at 0 - 20℃; for 6h; Reflux;	50%

ethyl 3-(benzyloxy)propanoate (127113-02-4) → ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃;	41%

diazoacetic acid ethyl ester (623-73-4) + methanol (67-56-1) → methyl methoxyacetate (6290-49-9) + ethyl 2-methoxyacetate (3938-96-3) + ethyl 3-hydroxypropanoate (623-72-3) + Ethoxyessigsaeure-methylester (17640-26-5)

Conditions	Yield
Irradiation;	A 3% B 40% C 8% D 20%

β-Propiolactone (57-57-8) + diethoxydibutyltin (1067-41-0) → ethyl 3-hydroxypropanoate (623-72-3) + 3-Hydroxy-propionic acid 2-ethoxycarbonyl-ethyl ester (80109-34-8)

Conditions	Yield
In chloroform Heating;	A 12% B 3.6%

3-iodopropanoic acid (141-76-4) + ethyl iodide (75-03-6) → ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
With silver(l) oxide

formaldehyd (50-00-0) + 1-ethoxyacetylene (927-80-0) → ethyl 3-hydroxypropanoate (623-72-3)

ethanol (64-17-5) + 3-Brompropionsaeure-O-trimethylsilylester (18187-28-5) → ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
(i) AgOCN, toluene, (ii) /BRN= 1718733/, H2SO4; Multistep reaction;

β-Propiolactone (57-57-8) + ethyl iodide (75-03-6) → ethyl 3-hydroxypropanoate (623-72-3) + acrylic acid methyl ester (292638-85-8) + ethyl acrylate (140-88-5)

Conditions	Yield
With 18-crown-6 ether; potassium methanolate 1) THF, 20 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;

ethyl glycidate (4660-80-4) → ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
With potassium biphenyle; water 1) THF, -80 deg C, 1 h, 2) THF, -80 deg C to RT; Yield given. Multistep reaction;

ethyl acrylate (140-88-5) → propan-1-ol (71-23-8) + propylene glycol (57-55-6) + ethyl 3-hydroxypropanoate (623-72-3) + Ethyl propionate (105-37-3)

Conditions	Yield
With 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; sodium acetate Product distribution; 1.) THF, 25 deg C, 3 h, 2.) room temp.;	A 1 % Chromat. B 7.4 % Chromat. C 4.2 % Chromat. D 17.8 % Chromat.

diethyl oxaloacetate (108-56-5) → Diethyl (S)-malate (691-84-9) + ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
With baker's yeast for 24h; Ambient temperature;

formaldehyd (50-00-0) + water (7732-18-5) + 1-ethoxyacetylene (927-80-0) → ethyl 3-hydroxypropanoate (623-72-3)

ethanol (64-17-5) + paracrylic acid → ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
at 150℃;

ethyl bromoacetate (105-36-2) + polyoxymethylene → ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
With diethyl ether; ethyl acetate; zinc

sodium salt of succinic acid monoethyl ester → ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
With water Electrolysis;

hydrochloride of β-amino-propionic acid ethyl ester → ethyl 3-hydroxypropanoate (623-72-3) + ethyl 3-chloropropanoate (623-71-2)

Conditions	Yield
With water; sodium nitrite

diethyl malonate (105-53-3) → propan-1-ol (71-23-8) + ethyl 3-hydroxypropanoate (623-72-3) + Ethyl propionate (105-37-3) + trimethyleneglycol (504-63-2)

Conditions	Yield
In ethanol at 199.84℃; under 15001.5 Torr; for 104h; Catalytic behavior; Time; Reagent/catalyst; Flow reactor;

oxirane (75-21-8) + ethanol (64-17-5) + carbon monoxide (201230-82-2) → ethyl 3-hydroxypropanoate (623-72-3)

Conditions	Yield
With immobilization of carbonylcobalt catalyst by poly(4-vinylpyridine)(P4VP) In tetrahydrofuran at 75℃; under 22502.3 Torr; for 15h; Autoclave;
With hydrogen; magnesium; triethylamine; cobalt(II) chloride at 0 - 70℃; under 75007.5 Torr; for 20h; Autoclave;

ethyl 3-hydroxypropanoate (623-72-3) + methylamine (74-89-5) → 3-hydroxy-N-methylpropionamide (6830-81-5)

Conditions	Yield
In methanol at 85℃; for 36h;	88%

ethyl 3-hydroxypropanoate (623-72-3) + tert-butyldimethylsilyl chloride (18162-48-6) → ethyl 3-((tert-butyldimethylsilyl)oxy)propanoate

Conditions	Yield
With 1H-imidazole In dichloromethane at 0 - 20℃; for 2h;	88%

3,4-dihydro-2H-pyran (110-87-2) + ethyl 3-hydroxypropanoate (623-72-3) → ethyl 3-(tetrahydropyran-2-yloxy)propanoate (847972-71-8)

Conditions	Yield
With hydrogenchloride In dichloromethane	79%

ethyl 3-hydroxypropanoate (623-72-3) → 3-hydroxypropionyl hydrazide (24535-11-3)

Conditions	Yield
With hydrazine hydrate In methanol; water at 20℃; for 5h; Cooling with ice;	79%

ethyl 3-hydroxypropanoate (623-72-3) + benzenesulfonyl chloride (1939-99-7) → Phenylmethansulfonoxy-essigsaeureethylester (58742-69-1)

Conditions	Yield
With triethylamine In diethyl ether at 20℃; for 12h;	69%

ethyl 3-hydroxypropanoate (623-72-3) + ethyl vinyl ether (109-92-2) → 3-Vinyloxy-propionic acid ethyl ester (213548-24-4)

Conditions	Yield
With mercury(II) trifluoroacetate for 1h; Ambient temperature;	64%

ethyl 3-hydroxypropanoate (623-72-3) + 6-chloro-N-(2,3-dimethylphenyl)-2-methylsulfonylpyrimidin-4-amine (86627-00-1) → ethyl 3-((4-chloro-6-((2,3-dimethylphenyl)amino)pyrimidin-2-yl)oxy)propanoate

Conditions	Yield
Stage #1: 6-chloro-N-(2,3-dimethylphenyl)-2-methylsulfonylpyrimidin-4-amine With lithium hexamethyldisilazane In tetrahydrofuran; hexane at 20℃; for 0.166667h; Stage #2: ethyl 3-hydroxypropanoate In tetrahydrofuran; hexane at 20℃; for 3h;	63%

ethyl 3-hydroxypropanoate (623-72-3) + N-(2,3-dihydro-1H-inden-4-yl)-2-methanesulfonyl-6-(trifluoromethyl)pyrimidin-4-amine → ethyl 3-((4-((2,3-dihydro-1H-inden-4-yl)amino)-6-(trifluoromethyl)pyrimidin-2-yl)oxy)propanoate

Conditions	Yield
Stage #1: N-(2,3-dihydro-1H-inden-4-yl)-2-methanesulfonyl-6-(trifluoromethyl)pyrimidin-4-amine With lithium hexamethyldisilazane In tetrahydrofuran; hexane at 20℃; for 0.166667h; Stage #2: ethyl 3-hydroxypropanoate In tetrahydrofuran; hexane at 20℃; for 4.5h;	57%

ethyl 3-hydroxypropanoate (623-72-3) + ({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetic acid → ethyl 3-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetoxy]propanoate

Conditions	Yield
Stage #1: ({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: ethyl 3-hydroxypropanoate With triethylamine In dichloromethane at 20℃; for 2h;	54%

ethyl 3-hydroxypropanoate (623-72-3) → acrylic acid (79-10-7) + ethyl acrylate (140-88-5)

Conditions	Yield
With ethanol; sulfuric acid; copper at 220℃; Product distribution / selectivity;	A 50% B 50 %Chromat.
With ethanol; NaH2PO4-silica at 250 - 275℃; Product distribution / selectivity;	A 21% B 14 - 49 %Chromat.

ethyl 3-hydroxypropanoate (623-72-3) + 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9, 86520-63-0, 87119-53-7, 92052-29-4, 121238-27-5, 142831-80-9, 127061-80-7) → C19H28O12

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -35℃; Inert atmosphere;	42.5%

ethyl 3-hydroxypropanoate (623-72-3) + 5-ethyl-5H-dibenzophosphole 5-oxide (55277-57-1) → 1-Hydroxy-4-(5-oxo-5H-5λ5-dibenzophosphol-5-yl)-pentan-3-one (104891-69-2)

Conditions	Yield
With lithium diisopropyl amide	38%

ethyl 3-hydroxypropanoate (623-72-3) + C14H12FN5O3 → C19H20FN5O5

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 15h; Inert atmosphere;	38%

ethyl 3-hydroxypropanoate (623-72-3) + C16H14FN5O3 → C21H22FN5O5

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 15h; Inert atmosphere;	38%

ethyl 3-hydroxypropanoate (623-72-3) + 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-3-methylbutanoic acid → 3-ethoxy-3-oxopropyl 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-3-methylbutanoate

Conditions	Yield
Stage #1: 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-3-methylbutanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: ethyl 3-hydroxypropanoate With triethylamine In dichloromethane at 20℃; for 6h;	37%

ethyl 3-hydroxypropanoate (623-72-3) + 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoic acid → 3-ethoxy-3-oxopropyl 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoate

Conditions	Yield
Stage #1: 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: ethyl 3-hydroxypropanoate With triethylamine In dichloromethane at 20℃; for 6h;	36%

ethyl 3-hydroxypropanoate (623-72-3) + 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-4-methylpentanoic acid → 3-ethoxy-3-oxopropyl 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-4-methylpentanoate

Conditions	Yield
Stage #1: 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-4-methylpentanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: ethyl 3-hydroxypropanoate With triethylamine In dichloromethane at 20℃; for 6h;	35%

ethyl 3-hydroxypropanoate (623-72-3) + C14H11FN4O4 → C19H19FN4O6

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 15h; Inert atmosphere;	31%

ethanol (64-17-5) + ethyl 3-hydroxypropanoate (623-72-3) + sodium cyanoacetic acid ethyl ester (18852-51-2) → diethyl 2-cyanoglutarate (7251-97-0)

Conditions	Yield
beim Zersetzen des Reaktionsprodukts mit verd. Salzsaeure;

ethyl 3-hydroxypropanoate (623-72-3) + 3-dichlorophosphanyloxy-propionic acid ethyl ester → bis-(2-ethoxycarbonyl-ethoxy)-chloro-phosphine

Conditions	Yield
With pyridine; diethyl ether

ethyl 3-hydroxypropanoate (623-72-3) + sodium cyanoacetic acid ethyl ester (18852-51-2) → diethyl 2-cyanoglutarate (7251-97-0)

Conditions	Yield
With ethanol

ethyl 3-hydroxypropanoate (623-72-3) + sodium cyanoacetic acid ethyl ester (18852-51-2) → ethyl 4-cyanobutyrate (10444-38-9)

Conditions	Yield
With ethanol bei der Zersetzung mit verd. Salzsaeure und nachfolgender Destillation der sauren Anteile des Reaktionsprodukts;

ethyl 3-hydroxypropanoate (623-72-3) → 3-hydrazino-propionic acid hydrazide (27438-25-1)

Conditions	Yield
With ethanol; hydrazine hydrate

Upstream product

• 141-76-4 3-iodopropanoic acid 
• 75-03-6 ethyl iodide 
• 623-73-4 diazoacetic acid ethyl ester 
• 67-56-1 methanol 
• 539-74-2 Ethyl 3-bromopropionate 
• 108-56-5 diethyl oxaloacetate 
• 50-00-0 formaldehyd 
• 7732-18-5 water 
• 927-80-0 1-ethoxyacetylene 
• 127113-02-4 ethyl 3-(benzyloxy)propanoate 
• 75-21-8 oxirane 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 473-81-4 glyceric acid 

Downstream Products

• 7251-97-0 diethyl 2-cyanoglutarate 
• 10444-38-9 ethyl 4-cyanobutyrate 
• 140-88-5 ethyl acrylate 
• 139747-28-7 3-Hydroxy-2-hydroxymethyl-3-(1-phenylsulfanyl-cyclohexyl)-propionic acid ethyl ester 
• 55408-10-1 1H-tetrazole-5-carboxylic acid ethyl ester 
• 125476-64-4 3-Benzyloxy-2-(hydroxymethyl)propionsaeure-ethylester 
• 504-63-2 trimethyleneglycol 

Relevant articles and documents

Method for preparing 3-hydracrylic acid ester derivative

The invention discloses a method for preparing a 3-hydracrylic acid ester derivative, which comprises the step of in the presence of an alcohol compound and a hydrodeoxygenation catalyst, reacting glyceric acid with hydrogen and the alcohol compound to obtain the 3-hydracrylic acid ester derivative, wherein the hydrodeoxygenation catalyst is a mixture of a supported metal catalyst and at least one supported metal oxide catalyst and/or at least one supported heteropolyacid catalyst. The method disclosed by the invention is green and environment-friendly, and the yield of the 3-hydracrylic acid ester derivative is high.

Preparation method of 3-oxetane carboxylic acid

The invention provides a preparation method of 3-oxetane carboxylic acid. The preparation method is characterized by carrying out hydrolytic esterification reaction, hydrogen pulling reaction and reduction reaction by taking 3-hydroxypropionitrile as a raw material, thus obtaining 2-benzyloxymethyl-1,3-propanediol; carrying out cyclization reaction, debenzylation reaction and oxidation reaction on2-benzyloxymethyl-1,3-propanediol, thus obtaining 3-oxetane carboxylic acid. According to the preparation method of 3-oxetane carboxylic acid, provided by the invention, a key intermediate 2-benzyloxymethyl-1,3-propanediol can be prepared just through three-steps reaction by taking 3-hydroxypropionitrile as the raw material, and 3-oxetane carboxylic acid can be prepared just through six-steps reaction in a final integral route, so that the reaction route is greatly shortened, and reaction steps are reduced; compared with a preparation method requiring ten-steps reaction in the prior art, theyield is higher, the operation is easy, and industrial production can be favorably realized.

Highly active Cu/SiO2 catalysts for hydrogenation of diethyl malonate to 1,3-propanediol

Cu/SiO2 catalysts prepared by the ammonia evaporation method were applied to hydrogenation of diethyl malonate to 1,3-propanediol. The calcination temperature played an important role in the structural evolution and catalytic performance of the Cu/SiO2 catalysts, which were systematically characterized by N2 adsorption-desorption, inductively coupled plasma-atomic emission spectroscopy, N2O chemisorption, X-ray diffraction, Fourier transform infrared spectroscopy, H2 temperature-programmed reduction, transmission electron microscopy, and X-ray photoelectron spectroscopy. When the Cu/SiO2 catalyst was calcined at 723 K, 90.7% conversion of diethyl malonate and 32.3% selectivity of 1,3-propanediol were achieved. Compared with Cu/SiO2 catalysts calcined at other temperatures, the enhanced catalytic performance of the Cu/SiO2 catalyst calcined at 723 K can be attributed to better dispersion of copper species, larger cupreous surface area and greater amount of copper phyllosilicate, which results in a higher ratio of Cu+/Cu0. The synergetic effect of Cu0 and Cu+ is suggested to be responsible for the optimum activity.