100542-64-1

Basic information

• Product Name: 2-[1-(4-chlorophenyl)propenyl]pyridine
• Synonyms: 2-[1-(4-chlorophenyl)propenyl]pyridine
• CAS NO: 100542-64-1
• Molecular Weight: 229.709
• Mol File: 100542-64-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-[1-(4-chlorophenyl)propenyl]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[1-(4-chlorophenyl)propenyl]pyridine(100542-64-1)
• EPA Substance Registry System: 2-[1-(4-chlorophenyl)propenyl]pyridine(100542-64-1)

Safety Data

• Hazardous Substances Data: 100542-64-1(Hazardous Substances Data)

Upstream product

• 17624-36-1 2-pyridyllithium 
• 27652-89-7 (4-chlorophenyl)-2-pyridylmethanol 
• 6318-51-0 2-(4-chlorobenzoyl)pyridine 
• 106-39-8 bromochlorobenzene 
• 1121-60-4 pyridine-2-carbaldehyde 
• 107776-02-3 1-(4-chlorophenyl)-1-(2-pyridyl)-1-propanol 
• 6285-05-8 4'-chloropropiophenone 

Downstream Products

• 861902-62-7 2-[2-(4-chlorophenyl)-3-methyloxiranyl]pyridine 

Relevant articles and documents

Slow-onset, long-duration, alkyl analogues of methylphenidate with enhanced selectivity for the dopamine transporter

Methylphenidate analogues, in which the carbomethoxy has been replaced by an alkyl group and with different phenyl substituents, have been synthesized and tested in monoamine transporter assays. As predicted from a pharmacophore model, most of the RR/SS diastereomers showed high potency as dopamine reuptake inhibitors. Analogues with a 4-chlorophenyl group and an unbranched initial alkyl atom had consistently enhanced selectivity for the dopamine transporter. The most potent compounds were those with a three- or four-carbon chain. The "inactive" RS/SR diastereomers showed substantial activity when the phenyl substituent was 3,4-dichloro. On a locomotor assay, one compound was found to have a slow onset and a long duration of action. The activity of these compounds provides additional evidence for a conformational/superposition model of methylphenidate with cocaine-like structures. A ketone analogue, obtained by hydrogenating a previously described vinylogous amide, had activity similar to that of methylphenidate.

Vinylogous amide analogs of methylphenidate

In an effort to produce compounds with longer durations of action, we attempted to synthesize ketone analogs of methylphenidate which, however, appear to be highly unstable due to a highly acidic proton alpha to the ketone and phenyl groups. Nevertheless, vinylogous amide by products have been synthesized and tested for activity at dopamine, norepinephrine, and serotonin transporters. The compounds were found to be weak inhibitors of monoamine reuptake despite rigid three dimensional structures that are quite similar to the global minimum of threo-(R,R)-methylphenidate. The structures were confirmed by X-ray crystallography.