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ChemicalBook--->CAS DataBase List--->80370-42-9

80370-42-9

80370-42-9 Structure

80370-42-9 Structure
IdentificationBack Directory
[Name]

Propanoicacid,2-formyl-3-oxo-,ethylester
[CAS]

80370-42-9
[Synonyms]

Ethyl Diformylacetate
Regadenoson impurity F
Regadenoson Impurity 9
EthylDiformylacetate>
Ethyl-2-forMyl-3-oxopropi...
(Ethoxycarbonyl)Malonaldehyde
Ethyl-2-forMyl-3-oxopropionate
Ethyl 2-formyl-3-oxopropanoate
Diformylacetic Acid Ethyl Ester
(Ethoxy carbonyl) malondialdehyde
2-ForMyl-3-Oxo-Propionsureethylester
Propanoicacid,2-formyl-3-oxo-,ethylester
2-Formyl-3-oxo-propanoic acid ethyl ester
2-Formyl-3-oxo-propionic Acid Ethyl Ester
Propanoicacid,2-formyl-3-oxo-,ethylester ISO 9001:2015 REACH
[EINECS(EC#)]

632-882-3
[Molecular Formula]

C6H8O4
[MDL Number]

MFCD11112084
[MOL File]

80370-42-9.mol
[Molecular Weight]

144.13
Chemical PropertiesBack Directory
[Boiling point ]

32°C/0.3mmHg(lit.)
[density ]

1.143±0.06 g/cm3(Predicted)
[refractive index ]

1.4710 to 1.4750
[storage temp. ]

Inert atmosphere,Store in freezer, under -20°C
[solubility ]

Chloroform, Methanol
[form ]

Oil
[pka]

1.55±0.59(Predicted)
[color ]

Clear Colorless to Pale Yellow
[λmax]

245nm(EtOH)(lit.)
[InChI]

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

HMFLBGNCDZYITR-UHFFFAOYSA-N
[SMILES]

C(OCC)(=O)C(C=O)C=O
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethyl 3,3-Diethoxypropionate-->Ethyl formate-->Sodium hydride-->Diethyl ether-->Hexane
[Preparation Products]

2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER-->2-Aminopyrimidine-5-carboxylic acid-->ISOXAZOLE-4-CARBOXYLIC ACID ETHYL ESTER-->ethyl 1-tert-butyl-1H-pyrazole-3-carboxylate-->ETHYL5-CYANO-6-METHYLNICOTINATE-->Ethyl pyrazole-4-carboxylate
Safety DataBack Directory
[HS Code ]

2918300090
Hazard InformationBack Directory
[Chemical Properties]

Propanoicacid,2-formyl-3-oxo-,ethylester is light yellow liquid
[Uses]

Propanoicacid,2-formyl-3-oxo-,ethylester is used cyclocondensation reactions for the the preparation of heterocyclic compounds such as polyfunctionally substituted pyridines.
[Synthesis Reference(s)]

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

Ethyl 3,3-Diethoxypropionate

10601-80-6

Ethyl formate

109-94-4

Propanoicacid,2-formyl-3-oxo-,ethylester

80370-42-9

Sodium hydride (2.46 g, 61.5 mmol) was accurately weighed in a dry 100-mL pear-shaped flask. It was washed sequentially with hexane and ether. The washed sodium hydride was suspended in ether (100 mL) and cooled in an ice bath to 0°C. Ethyl formate (24.84 mL, 308 mmol) was added slowly and dropwise, followed by ethyl 3,3-diethoxypropionate (5.98 mL, 30.8 mmol). The reaction mixture was stirred at room temperature for 15 hours to ensure complete reaction. After completion of the reaction, the mixture was slowly poured into ice water and the aqueous phase was washed with ether. The pH of the aqueous phase was adjusted to 1 with dilute hydrochloric acid and subsequently extracted with dichloromethane. The organic phases were combined, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford ethyl 2-formyl-3-oxopropanoate (3.29 g, 22.83 mmol, 74.2% yield) as a golden-yellow slurry.

[References]

[1] Patent: EP1364946, 2003, A1. Location in patent: Page/Page column 196
[2] Patent: US2005/256004, 2005, A1. Location in patent: Page/Page column 31-32
[3] Patent: WO2017/59191, 2017, A1. Location in patent: Paragraph 00441-00443
[4] Journal of Organic Chemistry, 1982, vol. 47, # 11, p. 2216 - 2217
[5] Tetrahedron, 2008, vol. 64, # 33, p. 7745 - 7758
Spectrum DetailBack Directory
[Spectrum Detail]

Propanoicacid,2-formyl-3-oxo-,ethylester(80370-42-9)1HNMR
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