Acrylophenone

Base Information

• Chemical Name: Acrylophenone
• CAS No.: 768-03-6
• Molecular Formula: C9H8O
• Molecular Weight: 132.162
• Hs Code.: 2914399090
• European Community (EC) Number: 212-190-4
• NSC Number: 174109
• UNII: O4QWF7V5AA
• DSSTox Substance ID: DTXSID30227607
• Nikkaji Number: J36.799K
• Wikipedia: Acrylophenone
• Wikidata: Q20707278
• Metabolomics Workbench ID: 130293
• ChEMBL ID: CHEMBL3099615
• Mol file: 768-03-6.mol

Synonyms:1-phenyl-2-propen-1-one;3-oxo-3-phenylpropene

Chemical Property of Acrylophenone

Chemical Property:

• Vapor Pressure: 0.29mmHg at 25°C
• Refractive Index: 1.525
• Boiling Point: 202.6 °C at 760 mmHg
• Flash Point: 73.7 °C
• PSA: 17.07000
• Density: 0.996 g/cm³
• LogP: 2.05530
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 132.057514874
• Heavy Atom Count: 10
• Complexity: 132

Purity/Quality:

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

1-Phenyl-2-propen-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC(=O)C1=CC=CC=C1
• Uses: 1-Phenyl-2-propen-1-one is a chemical reagent used in the synthesis of pharmaceutical agents. Used in the preparation of functionalized aminoindolizines as well as pyrano[3,2-x]coumarins.

Technology Process of Acrylophenone

There total 233 articles about Acrylophenone 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: 60.0%

1-Phenylprop-1-yne (673-32-5) → Phenyl vinyl ketone (768-03-6,26742-84-7) + 1-Phenylpropane-1,2-dione (579-07-7)

Guidance literature:

With 2,6-dichloropyridine N-oxide; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; at 60 ℃; regioselective reaction;

DOI:10.1002/anie.201504511

Reference yield: 45.0%

3-chloropropiophenone (936-59-4) + 4-isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester (1539-32-8) → 4-methyl-1-phenylpentan-1-one (2050-07-9) + Phenyl vinyl ketone (768-03-6,26742-84-7)

Guidance literature:

With di-tert-butyl peroxide; α,α,α-trifluorotoluene; copper; at 100 ℃; for 48h; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/acs.joc.9b02323

Reference yield: 27.0%

1,3,6-triphenyl-1,4,5,6-tetrahydropyridazine (137116-92-8) → benzaldehyde (100-52-7) + 4-benzoyl-2-phenyl-1,2,3,4-tetrahydroquinoline (137117-04-5,137117-05-6) + Phenyl vinyl ketone (768-03-6,26742-84-7)

Guidance literature:

With PPA; Polyphosphoric acid (PPA); at 110 ℃; for 0.5h; Yields of byproduct given;

upstream raw materials:

carbon disulfide

ethene

β-Propiolactone

benzene

Downstream raw materials:

3-(4-methylpiperazin-1-yl)-1-phenylpropan-1-one

3-(5-methylfuran-2-yl)-1-phenylpropan-1-one

3-dimethylaminopropiophenone

3-ethoxy-1-phenyl-propan-1-one-(2,4-dinitro-phenylhydrazone)

Refernces

• 1、 Deng, Guo-Jun,Huang, Huawen,Ji, Xiaochen,Wang, Chunlian. "Copper-catalyzed three-component: N -alkylation of quinazolinones and azoles". supporting information. p. 1200 - 1204. Retrieved 2022/02/21.
• 2、 Chen, Jinkang,Yin, Chuanliu,Zhou, Jian,Yu, Chuanming. "Cobalt(II)-Catalyzed C?H/N?H Functionalization and Annulation of N-(quinolin-8-yl)benzamide with Cyclopropanols". supporting information. p. 915 - 923. Retrieved 2021/02/06.