alpha-Phthalimidopropiophenone

Base Information

• Chemical Name: alpha-Phthalimidopropiophenone
• CAS No.: 19437-20-8
• Molecular Formula: C17H13NO3
• Molecular Weight: 279.295
• Hs Code.: 2925190090
• European Community (EC) Number: 673-682-6
• UNII: A7U6W3UB2N
• DSSTox Substance ID: DTXSID70334107
• Nikkaji Number: J2.102.025G
• Wikipedia: Phthalimidopropiophenone
• Wikidata: Q145057
• ChEMBL ID: CHEMBL1576765
• Mol file: 19437-20-8.mol

Synonyms:2-(1-oxo-1-phenylpropan-2-yl)isoindole-1,3-dione;alpha-phthalimidopropiophenone;cathinone phthalimide

Chemical Property of alpha-Phthalimidopropiophenone

Chemical Property:

• Vapor Pressure: 3.43E-08mmHg at 25°C
• Melting Point: 87-88°C
• Refractive Index: 1.633
• Boiling Point: 447.2 °C at 760 mmHg
• Flash Point: 204.4 °C
• PSA: 54.45000
• Density: 1.304 g/cm³
• LogP: 2.49190
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 279.08954328
• Heavy Atom Count: 21
• Complexity: 429

Purity/Quality:

98%min ^*data from raw suppliers

α-Phthalimidopropiophenone ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

Useful:

• Canonical SMILES: CC(C(=O)C1=CC=CC=C1)N2C(=O)C3=CC=CC=C3C2=O
• Description: α-Phthalimidopropiophenone is a cathinone analog that has been identified in capsules being distributed by the illicit drug market. The substitution of the phthalimido moiety for the typical α-amino group may increase the stability of this cathinone in storage. Alternatively, similar nitrogen-protected propiophenones have been shown to be metabolized in vivo to produce cathinone, suggesting that this compound may act as a prodrug. The physiological and toxicological properties of this compound are not known. This product is intended for forensic and research applications.
• Uses: α-Phthalimidopropiophenone is a cathinone related phenylethylamine. The phthalamide addition at the nitrogen increases the stability of the cathinone in storage. Potential prodrug.

Technology Process of alpha-Phthalimidopropiophenone

There total 8 articles about alpha-Phthalimidopropiophenone 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: 86.2%

potassium phtalimide (1074-82-4) + 2-bromo-1-phenyl-1-propanone (2114-00-3) → 2-(1-oxo-1-phenylpropan-2-yl) isoindoline-1,3-dione (19437-20-8)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.joc.0c01438

Reference yield: 68.0%

phenylboronic acid (98-80-6) + 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid pyridin-2-yl ester → 2-(1-oxo-1-phenylpropan-2-yl) isoindoline-1,3-dione (19437-20-8)

Guidance literature:

With palladium diacetate; triphenylphosphine; In 1,4-dioxane; at 50 ℃; for 10h;

DOI:10.1021/ol048513o

Reference yield: 56.0%

phthalimide (136918-14-4,85-41-6) + 1-phenyl-propan-1-one (93-55-0) → 2-(1-oxo-1-phenylpropan-2-yl) isoindoline-1,3-dione (19437-20-8)

Guidance literature:

With sodium percarbonate; ammonium iodide; In N,N-dimethyl-formamide; at 50 ℃; for 18h;

DOI:10.1021/jo5015855

upstream raw materials:

(2R)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanoylchloride

benzene

potassium phtalimide

2-bromo-1-phenyl-1-propanone

Downstream raw materials:

(+/-)-cathinone

2-amino-1-phenylpropan-1-one hydrochloride

2-(3-phenylbut-3-en-2-yl)isoindoline-1,3-dione

3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-trimethylsilanyloxy-butyronitrile

Refernces

• 1、 Jiang, Qing,Xu, Bin,Zhao, An,Jia, Jing,Liu, Tian,Guo, Cancheng. "Transition-metal-free oxidative α-C-H amination of ketones via a radical mechanism: Mild synthesis of α-amino ketones". . p. 8750 - 8756. Retrieved 2015/01/08.
• 2、 Tatamidani, Hiroto,Kakiuchi, Fumitoshi,Chatani, Naoto. "A new ketone synthesis by palladium-catalyzed cross-coupling reactions of esters with organoboron compounds". . p. 3597 - 3599. Retrieved 2007/10/03.