gamma-Phenyl-gamma-butyrolactone

Base Information

• Chemical Name: gamma-Phenyl-gamma-butyrolactone
• CAS No.: 1008-76-0
• Molecular Formula: C10H10 O2
• Molecular Weight: 162.188
• Hs Code.: 29322985
• European Community (EC) Number: 213-761-0
• NSC Number: 48048,24259
• DSSTox Substance ID: DTXSID50870831
• Nikkaji Number: J75.506K
• ChEMBL ID: CHEMBL191989
• Mol file: 1008-76-0.mol

Synonyms:1008-76-0;gamma-Phenyl-gamma-butyrolactone;5-phenyloxolan-2-one;5-Phenyldihydrofuran-2(3H)-one;4-Phenylbutyrolactone;4-Phenylbutanolide;2(3H)-Furanone, dihydro-5-phenyl-;4-Phenyl-4-butanolide;5-Phenyltetrahydrofuran-2-one;NSC 24259;4-Phenyl-4-hydroxybutanoic acid lactone;NSC 48048;4,5-Dihydro-5-phenyl-2(3H)-furanone;EINECS 213-761-0;.gamma.-Phenyl-.gamma.-butyrolactone;.gamma.-Phenylbutyrolactone;2(3H)-FURANONE, 4,5-DIHYDRO-5-PHENYL-;BRN 0125169;5-Phenyl-dihydro-furan-2-one;CHEMBL191989;5-17-10-00026 (Beilstein Handbook Reference);MFCD00005398;5-phenyloxolane-2-one;gamma-phenyl butyrolactone;4-phenyl-gamma-butyrolactone;SCHEMBL982856;ghl.PD_Mitscher_leg0.1063;AEUULUMEYIPECD-UHFFFAOYSA-;5-Phenyldihydro-2(3H)-furanone;DTXSID50870831;NSC24259;NSC48048;5-Phenyldihydro-2(3H)-furanone #;gamma -Phenyl- gamma -butyrolactone;BBL104384;BDBM50168005;NSC-24259;NSC-48048;STL558654;AKOS005216508;AKOS017344739;gamma-Phenyl-gamma-butyrolactone, 99%;LS-70463;2(3H)-Furanone, dihydro-5-phenyl- (8CI);CS-0214976;FT-0626620;P1321;D92106;EN300-210214;A910937;J-000243

Chemical Property of gamma-Phenyl-gamma-butyrolactone

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid after melting
• Vapor Pressure: 0.000793mmHg at 25°C
• Melting Point: 36-37 °C(lit.)
• Refractive Index: 1.5415-1.5435
• Boiling Point: 306 °C(lit.)
• Flash Point: 135.5°C
• PSA: 26.30000
• Density: 1.154g/cm³
• LogP: 2.06470
• Water Solubility.: Insoluble in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 171

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Phenyloxolan-2-one ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(=O)OC1C2=CC=CC=C2

Technology Process of gamma-Phenyl-gamma-butyrolactone

There total 140 articles about gamma-Phenyl-gamma-butyrolactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

succinylbenzene (2051-95-8) → 4,5-dihydro-5-phenyl-2(3H)-furanone (1008-76-0)

Guidance literature:

With ammonium hydroxide; titanium(III) chloride; In methanol; at 20 - 25 ℃; for 0.0833333h; pH=10 - 11;

DOI:10.1002/1099-0690(200210)2002:19<3326::AID-EJOC3326>3.0.CO;2-V

Reference yield: 94.0%

4-Phenylbutyric acid (1821-12-1) → 4,5-dihydro-5-phenyl-2(3H)-furanone (1008-76-0)

Guidance literature:

With 2,4,6-triphenylpyrylium tetrafluoroborate; iodine; In 1,2-dichloro-ethane; at 20 ℃; for 18h; Solvent; Irradiation;

DOI:10.1039/c8cc08594c

Reference yield: 92.0%

4-Phenyl-4-(trimethylsiloxy)butansaeure-methylester (106543-48-0) → 4,5-dihydro-5-phenyl-2(3H)-furanone (1008-76-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 0.25h;

DOI:10.1016/j.tet.2017.01.013

upstream raw materials:

styrene oxide

ethanol

sodium diethylmalonate

α-bromoacetophenone

Downstream raw materials:

γ-phenyl-γ-hydroxybutyric acid methylester

diethyl 2,2,3,3-tetramethylsuccinate

ethyl 6-hydroxy-6-phenyl-2,2-dimethyl-3-oxo-hexanoate

trans-2-(methylthio)-4-phenylbutyrolactone

Refernces

• 1、 Pea-Lpez, Miguel,Neumann, Helfried,Beller, Matthias. "Iron(II) pincer-catalyzed synthesis of lactones and lactams through a versatile dehydrogenative domino sequence". . p. 865 - 871. Retrieved 2015.
• 2、 Mebane, Robert C.,Grimes, Kimberly D.,Jenkins, Summer R.,Deardorff, Jonathan D.,Gross, Benjamin H.. "Deiodination of iodolactones by transfer hydrogenolysis using Raney nickel and 2-propanol". . p. 2049 - 2054. Retrieved 2002.
• 3、 Doyle, Michael P.,Bagheri, Vahid. "Regioselective Oxidations of Primary Alcohols in 1,4-Diols". . p. 4806 - 4808. Retrieved 1981.
• 4、 Tang, Yidan,Meador, Rowan I. L.,Malinchak, Casina T.,Harrison, Emily E.,McCaskey, Kimberly A.,Hempel, Melanie C.,Funk, Timothy W.. "(Cyclopentadienone)iron-Catalyzed Transfer Dehydrogenation of Symmetrical and Unsymmetrical Diols to Lactones". . p. 1823 - 1834. Retrieved 2020.
• 5、 Heiba,Dessau. "-". . p. 995,996. Retrieved 1971.
• 6、 Ando, Takashi,Kimura, Takahide,Leveque, Jean-Marc,Lorimer, J. Philip,Luche, Jean-Louis,Mason, Timothy J.. "Sonochemical reactions of lead tetracarboxylates with styrene". . p. 9561 - 9564. Retrieved 1998.
• 7、 Brouwer, Albert M.,De Bruin, Bas,Van Leeuwen, Nicole S.,Van Vliet, Kaj M.. "Visible-light-induced addition of carboxymethanide to styrene from monochloroacetic acid". . p. 398 - 408. Retrieved 2020.
• 8、 Yus, Miguel,Torregrosa, Rosario,Pastor, Isidro M.. "Masked ω-lithio ester enolates: Synthetic applications". . p. 330 - 348. Retrieved 2004.
• 9、 Zhang, Bijun,Han, Liuquan,Li, Tingting,Yan, Jie,Yang, Zhenping. "Ammonium iodide-promoted cyclization of aryl-substituted carboxylic acids". . p. 1608 - 1613. Retrieved 2014.
• 10、 Pastor, Isidro M.,Yus, Miguel. "Lithium- α-lithioacetate and β-lithiopropionate: Useful intermediates in organic synthesis". . p. 5335 - 5339. Retrieved 2000.