Langbahn Team – Weltmeisterschaft

2-Acetylbutyrolactone

2-Acetylbutyrolactone
Skeletal formula of 2-acetylbutyrolactone
Names
IUPAC name
3-acetyloxolan-2-one
Other names
3-acetyldihydrofuran-2(3H)-one
2-acetyl-γ-butyrolactone
Identifiers
3D model (JSmol)
Abbreviations ABL
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.488 Edit this at Wikidata
EC Number
  • 208-235-2
MeSH 2-acetylbutyrolactone
  • Key: OMQHDIHZSDEIFH-UHFFFAOYSA-N
  • InChI=1S/C6H8O3/c1-4(7)5-2-3-9-6(5)8/h5H,2-3H2,1H3
  • CC(=O)C1CCOC1=O
Properties
C6H8O3
Molar mass 128.127 g·mol−1
Appearance Colourless liquid
Density 1.19 g/cm3 [1]
Boiling point 107–108 °C (225–226 °F; 380–381 K) (at 7 hPa)[1]
Solubility Soluble in DMF,[2] methanol[3]
Hazards
GHS labelling:[4]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P271, P280, P302+P352, P304+P340, P305+P351+P338, P321, P362+P364, P403+P233, P405, P501
Flash point 113 °C (235 °F; 386 K)[1]
Safety data sheet (SDS) Sigma-Aldrich SDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Acetylbutyrolactone (ABL) is a derivative of γ-butyrolactone that is used as a precursor in organic synthesis, and it is used to identify primary amines through chemical fluorescence.[2]

Preparation

2-Acetylbutyrolactone can be prepared by a condensation reaction between an ester of acetic acid (such as ethyl acetate) with butyrolactone in an alkaline solution.[5]

2-Acetylbutyrolactone can also be prepared by reacting ethylene oxide with ethyl acetoacetate in alkaline conditions.[citation needed]

Uses

Spectrofluorimetry

2-Acetylbutyrolactone itself is only slightly fluorescent, but its derivatives show high UV fluorescence.[3][6] The carbonyl group readily reacts with amines to form Schiff bases. It is for this reason that 2-acetylbutyrolactone is frequently used to confirm the creation of amines during organic synthesis.[3] 2-Acetylbutyrolactone can also undergo a Japp–Klingemann reaction to form fluorescent molecules with arylamines.[6]

Drug precursor

Uses of 2-Acetylbutyrolactone also includes synthesis of:

  1. Risperidone
  2. Ritanserin
  3. Paliperidone
  4. Ocaperidone
  5. Seganserin
  6. Setoperone
  7. Metrenperone
  8. Pirenperone
  9. Novoldiamine (1-Diethylamino-4-aminopentane) [140-80-7]
  10. Clomethiazole
  11. Barmastine
  12. R 59-022 [93076-89-2]
  13. ID-4708 [42048-72-6].
  14. Santalene[7]
  15. α-methylene-γ-butyrolactones.[8]

References

  1. ^ a b c "α-Acetylbutyrolactone Safety Data Sheet". SigmaAldrich. January 20, 2020. Archived from the original on 2022-03-31. Retrieved March 30, 2022.
  2. ^ a b Sabry, Suzy M. (2006). "Application of 2-acetylbutyrolactone to spectrofluorimetry: Fluorescence properties of Schiff bases derived from 2-acetylbutyrolactone and spectrofluorimetric determination of primary amine-containing compounds". Journal of Pharmaceutical and Biomedical Analysis. 40 (5): 1057–1067. doi:10.1016/j.jpba.2005.08.036. PMID 16256289.
  3. ^ a b c Sabry, S M (2006). "Application of 2-acetylbutyrolactone to spectrofluorimetry: Fluorescence properties of Schiff bases derived from 2-acetylbutyrolactone and spectrofluorimetric determination of primary amine-containing compounds". Journal of Pharmaceutical and Biomedical Analysis. 40 (5): 1057–1067. doi:10.1016/j.jpba.2005.08.036. PMID 16256289.
  4. ^ "2-Acetylbutyrolactone". pubchem.ncbi.nlm.nih.gov. Retrieved 31 March 2022.
  5. ^ Koehler, Guenther (August 4, 1998). "Method for Preparing 2-Acetyl-y-Butyrolactone". United States Patent. Archived from the original on 2022-03-31. Retrieved March 30, 2022.
  6. ^ a b Sabry, S M (2006). "Enhanced Spectrophotometry of Sulfonamides with Novel 2-Acetylbutyrolactone Derivatives". Analytical Letters. 39 (13): 2591–2615. doi:10.1080/00032710600824748. S2CID 93950011.
  7. ^ Unnikrishnan, P. A.; Vatakencherry, P. A. (1992). "Syntheses of epi-β-Santalene, β-Santalene and an Isomer of β-Santalene with 4-Methyl-4-pentenyl Side Chain". Synthetic Communications. 22 (22): 3159–3168. doi:10.1080/00397919208021129.
  8. ^ Aghari, S (2006). "Reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-acetylbutyrolactone. Synthesis of functionalized α-methylene-γ-butyrolactones". Tetrahedron. 47 (25): 4297–4299. doi:10.1016/j.tetlet.2006.03.109.
Quelle: https://en.wikipedia.org/wiki/2-Acetylbutyrolactone