Benzylideneacetone

Base Information

• Chemical Name: Benzylideneacetone
• CAS No.: 1896-62-4
• Molecular Formula: C10H10O
• Molecular Weight: 146.189
• Hs Code.: 29143990
• European Community (EC) Number: 204-555-1,217-587-6
• NSC Number: 5605
• UNII: B03X40BMT5
• DSSTox Substance ID: DTXSID1031626
• Nikkaji Number: J5.357K,J80.339A
• Wikipedia: Benzylideneacetone
• Wikidata: Q4380955
• Metabolomics Workbench ID: 44990
• ChEMBL ID: CHEMBL73639
• Mol file: 1896-62-4.mol

Synonyms:4-phenyl-3-buten-2-one;4-phenylbutenone;benzalacetone;benzylideneacetone;benzylideneacetone, (E)-isomer;benzylideneacetone, (Z)-isomer;t-PBO;trans-4-phenyl-3-buten-2-one

Chemical Property of Benzylideneacetone

Chemical Property:

• Appearance/Colour: light yellow low melting crystalline mass
• Vapor Pressure: 0.01 mm Hg ( 25 °C)
• Melting Point: 39-42 °C(lit.)
• Refractive Index: 1.5836 (estimate)
• Boiling Point: 260.8 °C at 760 mmHg
• Flash Point: 65.6 °C
• PSA: 17.07000
• Density: 1.014 g/cm³
• LogP: 2.28880
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: alcohol: freely soluble(lit.)
• Water Solubility.: practically insoluble
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 146.073164938
• Heavy Atom Count: 11
• Complexity: 152

Purity/Quality:

99% ^*data from raw suppliers

trans-4-Phenyl-3-buten-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-43-42/43
• Safety Statements: 7-26-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: CC(=O)C=CC1=CC=CC=C1
• Isomeric SMILES: CC(=O)/C=C/C1=CC=CC=C1
• Uses: trans-4-Phenyl-3-buten-2-one is used in various synthetic preparations.

Technology Process of Benzylideneacetone

There total 340 articles about Benzylideneacetone 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: 92.0%

benzaldehyde (100-52-7) + isopropyl alcohol (67-63-0,8013-70-5) → (E)-benzalacetone (1896-62-4) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

at 225 ℃; for 24h;

DOI:10.1039/a808977i

Reference yield: 92.0%

benzaldehyde (100-52-7) → (E)-benzalacetone (1896-62-4) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With isopropyl alcohol; at 225 ℃; for 24h;

DOI:10.1071/C98156

Reference yield: 76.0%

trans-1-phenyl-1-butene (1005-64-7) → benzaldehyde (100-52-7) + (E)-benzalacetone (1896-62-4)

Guidance literature:

With trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate; tetrabutyl ammonium fluoride; In acetonitrile; at 20 ℃; for 0.166667h;

DOI:10.1055/s-0033-1338947

upstream raw materials:

4-methyleneoxetan-2-one

benzaldehyde

3-chloro-4-phenylbutan-2-one

6-(phenyl)-dihydro-2H-pyran-2,4(3H)-dione

Downstream raw materials:

5-Phenyl-2-morpholinothiophene

4-morpholin-4-yl-4-phenyl-butan-2-one

3,4-dimorpholino-4-phenylbutan-2-one

4-(3,4-dihydro-1H-[2]isoquinolyl)-4-phenyl-butan-2-one

Refernces

• 1、 Martínez, Sandra,Vallribera, Adelina,Cotet, Cosmin L.,Popovici, Mihaela,Martín, Laura,Roig, Anna,Moreno-Ma?as, Marcial,Molins, Elies. "Nanosized metallic particles embedded in silica and carbon aerogels as catalysts in the Mizoroki-Heck coupling reaction". . p. 1342 - 1345. Retrieved 2005.
• 2、 Molnár, Katalin,Takács, László,Kádár, Mihály,Faigl, Ferenc,Kardos, Zsuzsanna. "Z- and E-selective Horner–Wadsworth–Emmons reactions". . p. 1214 - 1224. Retrieved 2017.
• 3、 Coleman, Michael G.,Brown, Alec N.,Bolton, Brett A.,Guan, Hairong. "Iron-catalyzed oppenauer-type oxidation of alcohols". . p. 967 - 970. Retrieved 2010.
• 4、 Kjonaas, Richard A.. "Ketovinylation of Arylthallium Compounds Catalyzed by Lithium Tetrachloropalladate". . p. 3708 - 3710. Retrieved 1986.
• 5、 Noyce,Reed. "-". . p. 5539. Retrieved 1958.
• 6、 Shibata, Ikuya,Nishio, Masahiro,Baba, Akio,Matsuda, Haruo. "Preparation of α,β-Unsaturated Methyl Ketones from Diketene Using Bis(tributyltin) Oxide". . p. 1219 - 1222. Retrieved 1993.
• 7、 Guram, Anil S.,Jordan, Richard F.. "Synthesis and Reactivity of Cp2Zr(η2-C,N-CCH3)(1+). Regioselective Acetylation of Alkynes and Alkenes". . p. 5595 - 5597. Retrieved 1993.
• 8、 Giel, Marie-Claire,Barrow, Andrew S.,Smedley, Christopher J.,Lewis, William,Moses, John E.. "Aminium cation-radical catalysed selective hydration of (E)-aryl enynes". supporting information. p. 6991 - 6994. Retrieved 2021/07/21.
• 9、 Polaquini, Carlos R.,Marques, Beatriz C.,Ayusso, Gabriela M.,Mor?o, Luana G.,Sardi, Janaína C.O.,Campos, Débora L.,Silva, Isabel C.,Cavalca, Lúcia B.,Scheffers, Dirk-Jan,Rosalen, Pedro L.,Pavan, Fernando R.,Ferreira, Henrique,Regasini, Luis O.. "Antibacterial activity of a new monocarbonyl analog of curcumin MAC 4 is associated with divisome disruption". . . Retrieved 2021/02/22.