80370-42-9

Basic information

• Product Name: Propanoicacid,2-formyl-3-oxo-,ethylester
• Synonyms: Propanoicacid,2-formyl-3-oxo-,ethylester;Ethyl 2-formyl-3-oxopropanoate;2-Formyl-3-oxo-propanoic acid ethyl ester;Ethyl-2-forMyl-3-oxopropionate;Ethyl-2-forMyl-3-oxopropi...;(Ethoxycarbonyl)Malonaldehyde;2-ForMyl-3-Oxo-Propionsureethylester;Ethyl Diformylacetate
• CAS NO: 80370-42-9
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.13
• EINECS: 1592732-453-0
• Product Categories: Aliphatics;Intermediates;Miscellaneous Reagents
• Mol File: 80370-42-9.mol

Chemical Properties

• Boiling Point: 32°C/0.3mmHg(lit.)
• Flash Point: 67.423 °C
• Appearance: /
• Density: 1.143 g/cm³
• Vapor Pressure: 0.85mmHg at 25°C
• Refractive Index: 1.4710 to 1.4750
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform, Methanol
• PKA: 1.55±0.59(Predicted)
• CAS DataBase Reference: Propanoicacid,2-formyl-3-oxo-,ethylester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoicacid,2-formyl-3-oxo-,ethylester(80370-42-9)
• EPA Substance Registry System: Propanoicacid,2-formyl-3-oxo-,ethylester(80370-42-9)

Safety Data

• Hazardous Substances Data: 80370-42-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Propanoicacid,2-formyl-3-oxo-,ethylester is used as a key intermediate in cyclocondensation reactions for the preparation of heterocyclic compounds, such as polyfunctionally substituted pyridines. These compounds are valuable in the development of pharmaceuticals due to their diverse biological activities and potential applications in drug discovery and medicinal chemistry.
Used in Organic Synthesis:
In the field of organic synthesis, Propanoicacid,2-formyl-3-oxo-,ethylester is utilized as a versatile building block for the synthesis of a wide range of complex organic molecules. Its unique structure allows for various chemical transformations, making it a valuable tool for the preparation of target compounds in research and industrial applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 2216, 1982 DOI: 10.1021/jo00132a055

InChI:InChI=1/C6H8O4/c1-2-10-6(9)5(3-7)4-8/h3-5H,2H2,1H3

Synthetic route

ethyl 3,3-diethoxypropanoate (10601-80-6) + formic acid ethyl ester (109-94-4) → ethyl 2-formyl-3-oxopropanoate (80370-42-9)

Conditions	Yield
With sodium hydride In diethyl ether at 0 - 20℃; for 15h;	100%
With sodium hydride In diethyl ether at 0 - 20℃; for 15h;	100%
With sodium hydride In tetrahydrofuran at 0 - 20℃;	99.7%

3,3-diethoxypropionic acid methyl ester + formic acid ethyl ester (109-94-4) → ethyl 2-formyl-3-oxopropanoate (80370-42-9)

Conditions	Yield
With sodium hydride In diethyl ether; mineral oil at -10 - 20℃; for 21h; Inert atmosphere;	80%

ethyl 3,3-diethoxypropanoate (10601-80-6) → ethyl 2-formyl-3-oxopropanoate (80370-42-9)

Conditions	Yield
Multistep reaction;

methyl 3,3-dimethoxypropionate (7424-91-1) + formic acid ethyl ester (109-94-4) → ethyl 2-formyl-3-oxopropanoate (80370-42-9)

Conditions	Yield
With sodium hydride 1.) ether; 2.) ether, 5 deg C, 10 h; room temp., overnight; Yield given. Multistep reaction;

methyl 3,3-dimethoxypropionate (7424-91-1) → ethyl 2-formyl-3-oxopropanoate (80370-42-9)

Conditions	Yield
Stage #1: formic acid ethyl ester With sodium hydride In diethyl ether at 0℃; Argon atmosphere; Stage #2: methyl 3,3-dimethoxypropionate at 0 - 20℃; for 1.66667h; Argon atmosphere; Stage #3: With water

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 5-amino-4-bromo-1H-pyrazole (16461-94-2) → ethyl 3-bromopyrazolo[1,5-a]pyrimidine-6-carboxylate

Conditions	Yield
In ethanol for 1.33333h; Reflux;	100%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + methylhydrazine (60-34-4) → ethyl 1-methylpyrazole-4-carboxylate (85290-80-8)

Conditions	Yield
In ethanol at 5 - 20℃; Time;	99.1%
In ethanol at 5 - 20℃; for 16h; Time;	99%
In ethanol at 5 - 20℃; Concentration; Time;	99.1%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 2-hydrazinoadenosine (15763-11-8) → CVT 3127 (313348-16-2)

Conditions	Yield
With polyethylene glycol-600 In water at 45 - 55℃;	98.12%
In water at 30 - 50℃; Temperature;	95%
With acetic acid In methanol at 80℃; for 3h;	91%

2-hydroxyethylhydrazine (109-84-2) + ethyl 2-formyl-3-oxopropanoate (80370-42-9) → ethyl 1-(2-hydroxyethyl)-1H-pyrazole-4-carboxylate (782501-73-9)

Conditions	Yield
In ethanol at 0 - 20℃; for 48h;	96%
In ethanol at 0 - 20℃;	95%
In ethanol at 0 - 20℃;	95%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) → 4-ethoxycarbonylpyrazole (37622-90-5)

Conditions	Yield
With hydrazine dihydrochloride In ethanol at 0 - 20℃; for 32h;	92%
With hydrazine In ethanol at 0 - 20℃; for 24h;	86%
With hydrazine In ethanol at 0 - 20℃; for 17h;	72.4%
With hydrazine In ethanol at 20℃; for 17h;	72.4%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 2-hydrazinoadenosine (15763-11-8) + acetic acid (64-19-7) → ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxylate acetate salt

Conditions	Yield
In methanol at 80℃; for 3h;	92%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + (3-(difluoromethoxy)phenyl)hydrazine hydrochloride → ethyl 1-(3-(difluoromethoxy)phenyl)-1H-pyrazole-4-carboxylate (1415757-56-0)

Conditions	Yield
In ethanol at 0℃;	91%
Stage #1: ethyl 2-formyl-3-oxopropanoate; (3-(difluoromethoxy)phenyl)hydrazine hydrochloride In ethanol at 0℃; Stage #2: With sodium hydrogencarbonate In ethyl acetate	91%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + (3-(difluoromethoxy)phenyl)hydrazine hydrochloride (479581-64-1) → ethyl 1-(3-(difluoromethoxy)phenyl)-1H-pyrazole-4-carboxylate (1415757-56-0)

Conditions	Yield
In ethanol at 0℃;	91%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 3-hydroxymethylbenzamidinium acetate (1092566-66-9) → ethyl 2-(3-hydroxymethylphenyl)pyrimidine-5-carboxylate (1092566-68-1)

Conditions	Yield
With pyridine at 90℃; for 2h;	90%

3-Chloro-6-hydrazinopyridazine (17284-97-8) + ethyl 2-formyl-3-oxopropanoate (80370-42-9) → ethyl 1-(6-chloro-3-pyridazinyl)-1H-pyrazole-4-carboxylate

Conditions	Yield
In ethanol at 0 - 20℃; for 24h;	88%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 3-methyl-5-aminopyrazole (31230-17-8) → 2-methyl-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester

Conditions	Yield
With triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 0.5h; Reagent/catalyst; Solvent; Temperature;	86.3%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + N-4-methylphenylhydrazine (539-44-6) → ethyl 1-(4-methylphenyl)-1H-pyrazole-4-carboxylate

Conditions	Yield
In ethanol at 0 - 20℃; for 24h;	86%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 2-hydrazino-N6-methyladenosine → ethyl 1-(9-((3R,4S,5R)-tetrahydro-3,4-dihydroxy-5-(hydroxymethyl)furan-2-yl)-6-(methylamino)-9H-purin-2-yl)-1H-pyrazole-4-carboxylate

Conditions	Yield
In ethanol at 80℃;	85%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + (4-bromo-3-fluorophenyl)-hydrazine → C12H10BrFN2O2

Conditions	Yield
In ethanol at 0 - 20℃; for 18h; Sealed tube;	85%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 4-hydrazinylisoquinoline (15330-50-4) → ethyl 1-(isoquinolin-4-yl)-1H-pyrazole-4-carboxylate

Conditions	Yield
In isopropyl alcohol at 80℃;	84%

2-hydrazinobenzimidazole (15108-18-6) + ethyl 2-formyl-3-oxopropanoate (80370-42-9) → ethyl 1-(1H-benzimidazol-2-yl)-1H-pyrazole-4-carboxylate (1193403-34-7)

Conditions	Yield
In tetrahydrofuran; ethanol at 80℃; for 1.5h;	83%
In tetrahydrofuran; ethanol at 80℃; for 1.5h;	83%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 1,3-benzothiazol-2-ylhydrazine (615-21-4) → ethyl 1-(1,3-benzothiazol-2-yl)-1H-pyrazole-4-carboxylate

Conditions	Yield
In tetrahydrofuran; ethanol at 80℃; for 2h;	82%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 2-hydrazinyl-9H-purin 6-amine → ethyl 1-(6-amino-9H-purin-2-yl)-1H-pyrazole-4-carboxylate

Conditions	Yield
In ethanol for 2h; Reflux;	80%

3-Aminocrotononitrile (1118-61-2) + ethyl 2-formyl-3-oxopropanoate (80370-42-9) → 5-cyano-6-methylnicotinic acid ethyl ester (106944-54-1)

Conditions	Yield
Stage #1: ethyl 2-formyl-3-oxopropanoate With triethylamine In diethyl ether at 0℃; for 1h; Stage #2: With p-toluenesulfonyl chloride In N,N-dimethyl-formamide at -15 - 20℃; Stage #3: 3-Aminocrotononitrile With pyridine In N,N-dimethyl-formamide at 0 - 70℃; for 10h;	79%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 4-fluorophenylhydrazine (371-14-2) → ethyl 1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate (138907-73-0)

Conditions	Yield
With acetic acid In ethanol for 2h; Heating;	78%

2-hydroxyethylhydrazine (109-84-2) + ethyl 2-formyl-3-oxopropanoate (80370-42-9) → 1-(2-hydroxy-ethyl)-1H-pyrazole-4-carboxylic acid (1006469-47-1)

Conditions	Yield
Stage #1: 2-hydroxyethylhydrazine; ethyl 2-formyl-3-oxopropanoate In ethanol at 0 - 20℃; Stage #2: With ethanol; lithium hydroxide	77.1%

2-(2-hydrazinophenoxy)-5-methylphenol (897036-61-2) + ethyl 2-formyl-3-oxopropanoate (80370-42-9) → 1-[2-(2-hydroxy-4-methylphenoxy)phenyl]-1H-pyrazole-4-carboxylic acid ethyl ester

Conditions	Yield
With sodium acetate In ethanol for 3h; Heating / reflux;	77%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + benzenesufonyl hydrazide (80-17-1) → ethyl 1-benzenesulfonyl-1H-pyrazole-4-carboxylate

Conditions	Yield
In ethanol at 0 - 20℃; for 24h;	75%

5-(4-fluorophenyl)-1H-pyrazol-3-amine + ethyl 2-formyl-3-oxopropanoate (80370-42-9) → 2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester

Conditions	Yield
In ethanol at 80℃; for 3h; Inert atmosphere;	74.5%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + benzyl 4-(2-benzoylhydrazino)-4-(trifluoromethyl)piperidine-1-carboxylate → ethyl 1-[4-(trifluoromethyl)-4-piperidyl]pyrazole-4-carboxylate

Conditions	Yield
With hydrogenchloride In 1,4-dioxane	73.13%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 9-allyl 2-benzhydryl (2S,4aS,6aS,6bR,8aR,9S,10S,12aS,12bR,14bR)-10-hydrazinyl-2,4a,6a,6b,9,12a-hexamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2,9-dicarboxylate dihydrochloride → 9-allyl 2-benzhydryl (2S,4aS,6aS,6bR,8aR,9S,10S,12aS,12bR,14bR)-10-(4-(ethoxycarbonyl)-1H-pyrazol-1-yl)-2,4a,6a,6b,9,12a-hexamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2,9-dicarboxylate

Conditions	Yield
In ethanol at 20℃; for 2h;	72%

3-(methoxymethyl)-1H-pyrazol-5-amine (739366-03-1) + ethyl 2-formyl-3-oxopropanoate (80370-42-9) → ethyl 2-methoxymethylpyrazolo[1,5-a]pyrimidine-6-carboxylate (739366-04-2)

Conditions	Yield
In ethanol	69%

ethyl 2-formyl-3-oxopropanoate (80370-42-9) + 4-chlorophenylhydrazine hydrochloride (1073-70-7) → ethyl 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate (110821-33-5)

Conditions	Yield
In ethanol at 0 - 20℃; for 24h;	68%

Upstream product

• 109-94-4 formic acid ethyl ester 
• 7424-91-1 methyl 3,3-dimethoxypropionate 
• 10601-80-6 ethyl 3,3-diethoxypropanoate 

Downstream Products

• 869201-96-7 1-(5-carboxy-2-methyl-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester 
• 259543-04-9 Ethyl 1-(4-{2-[(acetylamino)methyl]-5oxo-2-hydroisoxazol4-yl}phenyl)pyrazole-4-carboxylate 
• 122535-03-9 ethyl furo[3,2-b]pyridine-6-carboxylate 
• 4485-89-6 1-anilino-3-phenyliminopropene 
• 80370-40-7 ethyl isoxazole-4-carboxylate 
• 1006469-47-1 1-(2-hydroxy-ethyl)-1H-pyrazole-4-carboxylic acid 

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