Tetrahydro-5-oxo-2- furancarboxyli

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CAS:4344-84-7
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Tetrahydro-5-oxo-2- furancarboxyli manufacturers

Tetrahydro-5-oxo-2- furancarboxyli Basic information
Product Name:Tetrahydro-5-oxo-2- furancarboxyli
Synonyms:Tetrahydro-5-oxo-2- furancarboxyli;2-Furancarboxylic acid, tetrahydro-5-oxo-;Inchi=1/C5H6o4/C6-4-2-1-3(9-4)5(7)8/H3H,1-2H2,(H,7,8;etrahydro-5-oxo-2- furancarboxyli;gamma-Butyrolactone-gamma-carboxylic acid;Tetrahydro-5-oxo-2-furoic acid;alpha-Hydroxyglutaryl lactone;Butyrolactonecarboxylic acid
CAS:4344-84-7
MF:C5H6O4
MW:130.1
EINECS:
Product Categories:Heterocyclic Compounds
Mol File:4344-84-7.mol
Tetrahydro-5-oxo-2- furancarboxyli Structure
Tetrahydro-5-oxo-2- furancarboxyli Chemical Properties
Melting point 48-50 °C
Boiling point 116-118 °C(Press: 1.5 Torr)
density 1.469±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly), DMSO (Slightly), Water (Sparingly)
form Solid
pka3.11±0.20(Predicted)
color White to Off-White
InChIInChI=1S/C5H6O4/c6-4-2-1-3(9-4)5(7)8/h3H,1-2H2,(H,7,8)
InChIKeyQVADRSWDTZDDGR-UHFFFAOYSA-N
SMILESO1C(=O)CCC1C(O)=O
Safety Information
MSDS Information
Tetrahydro-5-oxo-2- furancarboxyli Usage And Synthesis
UsesCarboxybutyrolactone is a structural analog of (±)-Paraconic Acid (P191200) and is used as a reagent in the synthesis of methylenecarboxybutyrolactones which have antibacterial activity.
DefinitionChEBI: 5-oxotetrahydrofuran-2-carboxylic acid is a gamma-lactone resulting from the formal intramolecular condensation of the alcoholic hydroxy group of 2-hydroxyglutaric acid with the carboxy group at position 5. It is a gamma-lactone and a monocarboxylic acid.
Synthesis
DL-Glutamic acid

617-65-2

Tetrahydro-5-oxo-2- furancarboxyli

4344-84-7

The general procedure for the synthesis of tetrahydro-5-oxo-2-furancarboxylic acid from 2-aminoglutaric acid is as follows: (1) 140 mL of concentrated hydrochloric acid was slowly added to a solution containing compound 1 (2-aminoglutaric acid, 270 mL of water as solvent) at room temperature and protected by nitrogen, and exothermic phenomena were observed. After the system became clear, it was cooled to 0°C. 70.3 g of sodium nitrite (dissolved in 200 mL of water) was slowly added to the system at 0°C, taking care to control the temperature. The system gradually turned green and turbid, and the dosing process continued for 15 minutes, keeping the temperature at about 2°C. The system was cooled to 0°C. After completion of the dropwise addition, the reaction was continued at 0°C. Subsequently, the reaction solution was concentrated directly to dryness at 50°C using an oil pump. The concentrated dry mass was pulped with 400 mL of ethyl acetate and filtered. The filter cake was again pulped once with 400 mL of ethyl acetate and then the cake was washed with 200 mL of ethyl acetate. All filtrates were combined and dried by pump at 45°C to give a final 104 g of yellow oily liquid (Compound 2).

References[1] Chemische Berichte, 1961, vol. 94, p. 2106 - 2114
[2] Chemistry and Industry (London, United Kingdom), 1959, p. 1413
[3] Justus Liebigs Annalen der Chemie, 1890, vol. 260, p. 128
[4] Patent: CN106748972, 2017, A. Location in patent: Paragraph 0022; 0023; 0024; 0030
Tetrahydro-5-oxo-2- furancarboxyli Preparation Products And Raw materials
Raw materialsDiethyl malonate-->DL-Glutamic acid-->epoxypropionic acid-->Hydrochloric acid-->Sodium nitrite
Tag:Tetrahydro-5-oxo-2- furancarboxyli(4344-84-7) Related Product Information
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