Chemistry:2-Acetylbutyrolactone

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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
EC Number
  • 208-235-2
MeSH 2-acetylbutyrolactone
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
Safety data sheet Sigma-Aldrich SDS
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319, H335
P261, P271, P280, P302+352, P304+340, P305+351+338, P321, P362+364Script error: No such module "Preview warning".Category:GHS errors, P403+233, P405, P501
Flash point 113 °C (235 °F; 386 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

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. ↑ 1.0 1.1 1.2 "α-Acetylbutyrolactone Safety Data Sheet". January 20, 2020. https://www.sigmaaldrich.com/US/en/sds/aldrich/a13409. 
  2. ↑ 2.0 2.1 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" (in en). Journal of Pharmaceutical and Biomedical Analysis 40 (5): 1057–1067. doi:10.1016/j.jpba.2005.08.036. PMID 16256289. https://linkinghub.elsevier.com/retrieve/pii/S0731708505006114. 
  3. ↑ 3.0 3.1 3.2 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" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/10601#section=Safety-and-Hazards. 
  5. ↑ Koehler, Guenther (August 4, 1998). "Method for Preparing 2-Acetyl-y-Butyrolactone". https://patents.google.com/patent/US5789603A/en. 
  6. ↑ 6.0 6.1 Sabry, S M (2006). "Enhanced Spectrophotometry of Sulfonamides with Novel 2-Acetylbutyrolactone Derivatives". Analytical Letters 39 (13): 2591–2615. doi:10.1080/00032710600824748. 
  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. 



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