Phenylacetaldehyde

Base Information

• Chemical Name: Phenylacetaldehyde
• CAS No.: 122-78-1
• Deprecated CAS: 2170235-75-1
• Molecular Formula: C8H8O
• Molecular Weight: 120.151
• Hs Code.: 29122990
• European Community (EC) Number: 204-574-5
• NSC Number: 406309
• UNII: U8J5PLW9MR
• DSSTox Substance ID: DTXSID3021483
• Nikkaji Number: J2.494E
• Wikipedia: Phenylacetaldehyde
• Wikidata: Q424998
• RXCUI: 1367159
• Metabolomics Workbench ID: 38835
• ChEMBL ID: CHEMBL1233464
• Mol file: 122-78-1.mol

Synonyms:phenylacetaldehyde

Chemical Property of Phenylacetaldehyde

Chemical Property:

• Appearance/Colour: colourless to slightly yellow liquid
• Vapor Pressure: 0.368mmHg at 25°C
• Melting Point: -10 °C(lit.)
• Refractive Index: n20/D 1.535(lit.)
• Boiling Point: 198 °C at 760 mmHg
• Flash Point: 89.2 °C
• PSA: 17.07000
• Density: 1.029 g/cm³
• LogP: 1.42800
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: 2.21g/l slightly soluble
• Water Solubility.: 2.210 g/L (25 ºC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 120.057514874
• Heavy Atom Count: 9
• Complexity: 82.6

Purity/Quality:

99% ^*data from raw suppliers

Phenylacetaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,F
• Hazard Codes: Xn,F
• Statements: 22-36/37/38-43-11
• Safety Statements: 26-36-37-24-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: C1=CC=C(C=C1)CC=O
• Description: Phenylacetaldehyde is an organic compound which can be naturally found in buckwheat, flowers, and communication pheromones from various insect orders. It is commonly used for the preparation of fragrance as well as flavors, and applied in flavored cigarettes and beverages because of its honey-like sweet character. It is also applied in the synthesis of polymers, such as polyesters, as a rate controlling additive in polymerization reactions and used in the preparation of more complex chemicals like resmethrin, where it acts as a building block. Besides, the naturally sweet odor of phenylacetaldehyde makes it an insect attractant, which is effective to ensnare pests in blacklight trap. Its application also involves in the field of medicine, in which it is responsible for the antibiotic activity of maggot therapy.
• Uses: Phenylacetaldehyde is used in perfume compositions, in particular for hyacinth and rose notes. Phenylacetaldehyde was used in a study to analyse the role of plant derived volatile chemicals on foraging of 1st instar Helicoverpa armigera. Phenylacetaldehyde is an insect attractant and can be used in blacklight trap for pests. In perfumery; intermediate in organic synthesis. Phenylacetaldehyde is used for the preparation of fragrances and polymers like polyesters, which find application as a rate controlling additive in polymerization reactions. It is an active component of fragrances and floral scent due to its honey-like sweet character and finds application in flavored cigarettes and beverages. It is an insect attractant and utilized in blacklight trap for pests. It is also used as a building block in the synthesis of more complex chemicals, such as resmethrin. Furthermore, it is used in association with acetic anhydride and allyltrimethylsilane in three-component coupling process catalyzed by LiBF4 providing homoallylic acetates.

Technology Process of Phenylacetaldehyde

There total 720 articles about Phenylacetaldehyde 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: 83.0%

1-phenyl-2-bromoethane (103-63-9) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + phenylacetaldehyde (122-78-1)

Guidance literature:

With trimethylamine-N-oxide; In dimethyl sulfoxide; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(00)97742-6

Reference yield: 81.81%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → styrene oxide (96-09-3) + phenylacetaldehyde (122-78-1) + benzaldehyde (100-52-7) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With tert.-butylhydroperoxide; In water; acetonitrile; at 70 ℃; for 6h; Solvent; Temperature; Time;

DOI:10.1016/j.catcom.2017.08.017

Reference yield: 44.0%

β-styrylmagnesium bromide (30094-01-0,35672-47-0,56516-81-5) + 2-Chloronitrobenzene (88-73-3) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + phenylacetaldehyde (122-78-1) + 7-chloro-3-phenyl-1H-indole (124608-85-1)

Guidance literature:

In tetrahydrofuran; at -40 ℃;

DOI:10.1016/S0040-4039(01)93730-X

upstream raw materials:

N-Formylpiperidine

benzylmagnesium chloride

styrene oxide

acetic acid

Downstream raw materials:

(E)-N-(2-phenylethenyl)morpholine

5-methyl-4-phenethylidene-2-phenyl-2,4-dihydro-pyrazol-3-one

1-phenethyl-4-phenyl-piperidine-4-carboxylic acid ethyl ester

1,5-dimethyl-4-phenethylamino-2-phenyl-1,2-dihydro-pyrazol-3-one

Refernces

• 1、 Matsuda,Sugishita. "-". . p. 1446,1449. Retrieved 1962.
• 2、 Razenberg, Johannes A. S. J.,Nolte, Roeland J. M.,Drenth, Wiendelt. "Mechanism of Alkene Epoxidation by a Cytochrome P-450 Model. Effect of Additives". . p. 277 - 279. Retrieved 1986.
• 3、 Fujitsu, Hiroshi,Shirahama, Shinichi,Matsumura, Eiichi,Takeshita, Kenjiro,Mochida, Isao. "Catalytic Hydrogenation of Styrene Oxide with Cationic Rhodium Complexes". . p. 2287 - 2290. Retrieved 1981.
• 4、 Paret, Nicolas,Trachsel, Alain,Berthier, Damien L.,Herrmann, Andreas. "Controlled release of encapsulated bioactive volatiles by rupture of the capsule wall through the light-induced generation of a gas". . p. 2275 - 2279. Retrieved 2015.
• 5、 Chen, Tse-Hong,Kwong, Ka Wai,Carver, Aaron,Luo, Weilong,Zhang, Rui. "Enhanced iron(III) corrole-catalyzed oxidations with iodobenzene diacetate: Synthetic and mechanistic investigations". . p. 121 - 126. Retrieved 2015.
• 6、 Kaithal, Akash,Schmitz, Marc,H?lscher, Markus,Leitner, Walter. "On the Mechanism of the Ruthenium-catalyzed β-methylation of Alcohols with Methanol". . p. 781 - 787. Retrieved 2020.
• 7、 Fronza, Giovanni,Fuganti, Claudio,Grasselli, Piero,Servi, Stefano,Zucchi, Gioia,et al.. "Natural Abundance 2H Nuclear Magnetic Resonance Study of the Origin of 2-Phenylethanol and 2-Phenylethyl Acetate". . p. 439 - 443. Retrieved 1995.
• 8、 Davies, Thomas E.,Kondrat, Simon A.,Nowicka, Ewa,Kean, Joseline L.,Harris, Christopher M.,Socci, Joseph M.,Apperley, David C.,Taylor, Stuart H.,Graham, Andrew E.. "Nanoporous alumino- and borosilicate-mediated Meinwald rearrangement of epoxides". . p. 17 - 24. Retrieved 2015.
• 9、 Zhou,Tang,Lu,Wei,Li,Xia. "Co2+-exchanged MOR and 5A zeolites as efficient solid catalysts for the epoxidation of styrene with air". . p. 124 - 128. Retrieved 2014.
• 10、 Bata, Zsófia,Qian, Renzhe,Roller, Alexander,Horak, Jeannie,Bencze, László Csaba,Paizs, Csaba,Hammerschmidt, Friedrich,Vértessy, Beáta G.,Poppe, László. "A Methylidene Group in the Phosphonic Acid Analogue of Phenylalanine Reverses the Enantiopreference of Binding to Phenylalanine Ammonia-Lyases". . p. 2109 - 2120. Retrieved 2017.