3-Phenylprop-2-enyl acetate

Base Information

• Chemical Name: 3-Phenylprop-2-enyl acetate
• CAS No.: 103-54-8
• Molecular Formula: C11H12O2
• Molecular Weight: 176.215
• Hs Code.: 29153900
• DSSTox Substance ID: DTXSID2044765
• Wikidata: Q61734302
• Metabolomics Workbench ID: 130637
• ChEMBL ID: CHEMBL3185011
• Mol file: 103-54-8.mol

Synonyms:DTXSID2044765;3-phenylprop-2-enyl acetate;MFCD00008722;(Acetoxymethyl)styrene;CHEMBL3185011;acetic acid 3-phenyl-allyl ester;AKOS032455783;NCGC00248267-01;SY033240;FT-0623840

Chemical Property of 3-Phenylprop-2-enyl acetate

Chemical Property:

• Appearance/Colour: Colorless to yellow clear liquid
• Vapor Pressure: 0.0094mmHg at 25°C
• Melting Point: 30 °C
• Refractive Index: n20/D 1.541(lit.)
• Boiling Point: 265 °C at 760 mmHg
• Flash Point: 130.5 °C
• PSA: 26.30000
• Density: 1.054 g/cm³
• LogP: 2.26290
• Storage Temp.: 2-8°C
• Solubility.: alcohol: soluble(lit.)
• Water Solubility.: 176.2mg/L(temperature not stated)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 176.083729621
• Heavy Atom Count: 13
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

Cinnamyl Acetate >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC=CC1=CC=CC=C1
• Uses: Cinnamyl Acetate is used in preparation and characterization of cinnamon essential oil nanocapsules and comparison of volatile components and antibacterial ability of cinnamon essential oil before and after encapsulation. Perfumery (fixative), flavoring.

Technology Process of 3-Phenylprop-2-enyl acetate

There total 89 articles about 3-Phenylprop-2-enyl acetate 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: 99.0%

3-Phenylpropenol (104-54-1) + acetic anhydride (108-24-7) → cinnamyl acetate (103-54-8)

Guidance literature:

With Cp₂Ti(OSO₂C₈F₁₇)2; at 20 ℃; for 0.0833333h; Neat (no solvent);

DOI:10.1016/j.jorganchem.2010.01.025

Reference yield: 97.0%

Isopropenyl acetate (108-22-5) + 3-Phenylpropenol (104-54-1) → cinnamyl acetate (103-54-8)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1016/j.tetlet.2017.09.007

Reference yield: 95.0%

1-Phenylprop-1-yne (673-32-5) + acetic acid (64-19-7,77671-22-8) → cinnamyl acetate (103-54-8)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In toluene; at 110 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tet.2011.02.008

upstream raw materials:

1,1-diacetoxy-3-phenylprop-2-ene

3-Phenylpropenol

acetic anhydride

1-Phenyl-2-propen-1-ol

Downstream raw materials:

2-Ethoxymethyl-1-phenyl-propen-⁽¹⁾-ol-⁽³⁾

4-nitro-3,4-diphenyl-1-butene

4-nitro-1,4-diphenyl-1-butene

1-phenylhept-1-ene

Refernces

• 1、 Temperini, Andrea,Minuti, Lucio,Morini, Tommaso,Rosati, Ornelio,Piazzolla, Francesca. "Isopropenyl acetate: A cheap and general acylating agent of alcohols under metal-free conditions". . p. 4051 - 4053. Retrieved 2017.
• 2、 Yue, Hongmei,Yu, Hao,Liu, Sheng,Xu, Chunli. "Ag-Cu nanoparticles as efficient catalysts for transesterification of β-keto esters under acid/base-free conditions". . p. 19041 - 19051. Retrieved 2016.
• 3、 Shirini, Farhad,Zolfigol, Mohammad Ali,Khaleghi, Mahroo. "Silica chloride as a mild and efficient reagent for acetylation of alcohols". . p. 1999 - 2002. Retrieved 2003.
• 4、 Asadolah,Heravi,Hekmatshoar. "Solvent-free DABCO-catalyzed one-pot conversion of tetrahydropyranyl ethers into acetates by the action of bismuth(III) nitrate under microwave irradiation". . p. 1110 - 1111. Retrieved 2009.
• 5、 Uemura, Sakae,Fukuzawa, Shin-ichi,Toshimitsu, Akio,Okano, Masaya. "PALLADIUM-CATALYZED ALLYLIC OXIDATION OF OLEFINS BY t-BUTYL HYDROPEROXIDE AND TELLURIUM(IV) OXIDE". . p. 87 - 90. Retrieved 1982.
• 6、 Wolfe, Saul,Campbell, Peter G. C.. "SECONDARY TRITIUM ISOTOPE EFFECTS, A USEFUL MECHANISTIC PROBE FOR THE STUDY OF ACETOXYL PARTICIPATION AND TRANSFER". . p. 1227 - 1230. Retrieved 1982.
• 7、 Yadav, Ganapati D.,Devendran, Saravanan. "Lipase catalyzed synthesis of cinnamyl acetate via transesterification in non-aqueous medium". . p. 496 - 502. Retrieved 2012.
• 8、 Booker-Milburn, Kevin I.,Knowles, Jonathan P.,Latter, Francesca,Schwarz, Maria,Steeds, Hannah G.. "Pd-Catalyzed Cascade Reactions of Aziridines: One-Step Access to Complex Tetracyclic Amines". . p. 4986 - 4990. Retrieved 2021.
• 9、 Li, Xiaohan,Sun, Bin,Zhou, Jiadi,Jin, Can,Yu, Chuangming. "Regioselective Acetoxylation of Terminal Olefins Using a Palladium(II)–Thiadiazole Catalyst". . p. 2635 - 2638. Retrieved 2019.
• 10、 Bhosale, Manohar A.,Ummineni, Divya,Sasaki, Takehiko,Nishio-Hamane, Daisuke,Bhanage, Bhalchandra M.. "Magnetically separable γ-Fe2O3 nanoparticles: An efficient catalyst for acylation of alcohols, phenols, and amines using sonication energy under solvent free condition". . p. 8 - 17. Retrieved 2015.