2-Acetylbutyrolactone

2-Acetylbutyrolactone
Skeletal formula of 2-acetylbutyrolactone
Skeletal formula of 2-acetylbutyrolactone
Names
Preferred 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
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).
Infobox references

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 γ-butyrolactone in an alkaline solution.[5]

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

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 (alphabetical order):

  1. Barmastine
  2. Clomethiazole
  3. ID-4708 [42048-72-6]
  4. Metrenperone
  5. Morocromen (Ex 35)[7][8]
  6. Novoldiamine (1-Diethylamino-4-aminopentane) [140-80-7]
  7. Ocaperidone
  8. Paliperidone
  9. Pirenperone
  10. Risperidone
  11. Ritanserin
  12. R 59-022 [93076-89-2]
  13. Santalene[9]
  14. Seganserin
  15. Setoperone
  16. α-methylene-γ-butyrolactones.[10]

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. ^ Karl Heinz Becker, et al. US3930003 (1975 to Troponwerke Dinklage and Co).
  8. ^ Castañer, J., Hillier, K. (1977). "Morocromen". Drugs of the Future. 2 (2): 120. doi:10.1358/dof.1977.002.02.998240. ISSN 0377-8282.
  9. ^ 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.
  10. ^ 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.
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