60691-88-5

Usage

Uses

Used in Medical Research:
(E)-3-(4-chlorophenyl)prop-2-en-1-amine is used as a research chemical for [application reason] understanding the effects of psychoactive substances on the central nervous system. Its study contributes to the broader knowledge of psychopharmacology and may aid in the development of new treatments for various neurological and psychiatric conditions.
Used in Illicit Drug Preparations:
Although not a recommended or legal application, (E)-3-(4-chlorophenyl)prop-2-en-1-amine has been used in the past as an ingredient in illicit drug preparations. However, due to its potential for abuse and harm, it has been controlled or banned in some jurisdictions.

Upstream product

• 24583-70-8 3-(4-chlorophenyl)-2-propene-1-ol 
• 22621-98-3 (E)-2-(3-(4-chlorophenyl)allyl)isoindoline-1,3-dione 
• 637-87-6 1-Chloro-4-iodobenzene 
• 24583-70-8 (E)-3-(p-chlorophenyl)prop-2-en-1-ol 
• 103979-29-9 para-chlorocinnamyl chloride 

Downstream Products

• 1417560-16-7 (E)-N-[3-(4-chlorophenyl)allyl]acetamide 
• 98978-00-8 (E)-N-<3-(4-chlorophenyl)-2-propenyl>-N-methyl-1-naphthalenemethanamine 
• 1000979-70-3 4-methyl-N-[(2E)-3-(4-chlorophenyl)-2-propenyl]benzenesulfonamide 
• 1397699-28-3 C₁₅H₁₃ClO₂S 
• 1355342-88-9 2-chloro-N-[4,5-dichloro-2-[[1-[(2E)-3-(4-chlorophenyl)-2-propen-1-yl]-3-azetidinyl]oxy]phenyl]-4-pyridinecarboxamide 
• 1355345-59-3 4,5-dichloro-2-[[1-[(2E)-3-(4-chlorophenyl)-2-propen-1-yl]-3-azetidinyl]oxy]benzenamine 
• 1355345-58-2 1-[(2E)-3-(4-chlorophenyl)-2-propen-1-yl]-3-(4,5-dichloro-2-nitrophenoxy)azetidine 
• 944819-01-6 5-(2,4-dichloro-phenyl)penta-2,4-dienoic acid [3-(4-chloro-phenyl)-allyl]-amide 
• 944819-00-5 5-(2,4-dichloro-phenyl)-penta-2,4-dienoic acid [3-(4-chloro-phenyl)-allyl]-amide 
• 21156-92-3 Chloressigsaeure-(4-chlorcinnamylamid) 

Relevant academic research and scientific papers

Direct use of allylic alcohols and allylic amines in palladium-catalyzed allylic amination

Allylic alcohols and allylic amines were directly utilized in a Pd-catalyzed hydrogen-bond-activated allylic amination under mild reaction conditions in the absence of any additives. The cooperative action of a Pd-catalyst and a hydrogen-bonding solvent is most likely responsible for its high reactivity. The catalytic system is compatible with a variety of functional groups and can be used to prepare a wide range of linear allylic amines in good to excellent yields. Furthermore, this methodology can be easily applied to the one-step synthesis of two drugs, cinnarizine and naftifine, on a gram scale.

Rhodium/Yanphos-Catalyzed Asymmetric Interrupted Intramolecular Hydroaminomethylation of trans-1,2-Disubstituted Alkenes

The first interrupted asymmetric hydroaminomethylation reaction was developed. The challenging trans-1,2-disubstituted olefins were employed as substrates, and a series of valuable chiral pyrrolidinones and pyrrolidines were obtained in high yields with high regioselectivities and excellent enantioselectivities. Several synthetic transformations were conducted, demonstrating the high synthetic utility of our method. A creative route for the synthesis of vernakalant and Enablex was also developed.

The Heck reaction of polymer-supported allylamine with aryl iodides

The Heck reaction of Wang resin-bound allylamine with aryl iodides produces various, substituted cinnamylamines. The catalyst and additive system consisting of palladium(II) acetate, n-Bu4NOAc and potassium chloride, in addition to potassium carbonate in N,N-dimethylformamide, accomplishes a regioselective γ-arylation. By utilising the easily formed and stable carbamate linker on Wang resin, the incompatibility of free amines with the palladium catalyst is avoided. The cinnamylamine products are cleaved from the resin with trifluoroacetic acid under mild conditions and are converted into chromatographically separable acetamides. Our solid-phase method offers a new alternative for the synthesis of cinnamylamine derivatives, as biologically interesting compounds and useful synthetic intermediates.

Heck reaction of arenediazonium salts with N,N-diprotected allylamines. Synthesis of cinnamylamines and indoles

Novel palladium-catalyzed reactions of arenediazonium tetrafluoroborates with N,N-diprotected allylamines are presented. The reaction of arenediazonium tetrafluoroborates with N,N-(Boc)2 allylamine allows for an easy approach to cinnamylamines whereas using 2-alkynyl-N-(allyl) trifluoroacetanilides and 2-iodo-N-(allyl)trifluoroacetanilide the reaction provides a useful tool for appending indole rings to aniline fragments.

Highly Stereoselective Route to (E)-Allyl Amines via Vinyltri-n-butylphosphonium Salts (Schweizer Reaction)

The reaction of vinyltri-n-butylphosphonium salts, aldehydes, and sodiophthalimide in THF gave good yields of the allylic phthalimides with high E stereoselectivity (75-100percent).The use of the vinyltriphenylphosphonium salts (Schweizer reaction) gave the allyl phthalimide with the Z isomer predominating.A study of the phthalimide cation and the effect of added lithium salt showed some reversal in the olefin geometry but in general the selectivity was only 3:1