850352-47-5

Basic information

• Product Name: 2-BroMo-1-(3,4-dichlorophenyl)butan-1-one
• Synonyms: 2-BroMo-1-(3,4-dichlorophenyl)butan-1-one
• CAS NO: 850352-47-5
• Molecular Formula: C₁₀H₉BrCl₂O
• Molecular Weight: 295.98786
• Mol File: 850352-47-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-BroMo-1-(3,4-dichlorophenyl)butan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BroMo-1-(3,4-dichlorophenyl)butan-1-one(850352-47-5)
• EPA Substance Registry System: 2-BroMo-1-(3,4-dichlorophenyl)butan-1-one(850352-47-5)

Safety Data

• Hazardous Substances Data: 850352-47-5(Hazardous Substances Data)

Upstream product

• 6582-45-2 1-(3,4-dichlorophenyl)butan-1-one 
• 6574-99-8 3,4-dichloro-benzonitrile 

Downstream Products

• 1193779-74-6 2-(tert-butylamino)-3',4'-dichlorobutyrophenone 

Relevant articles and documents

Unexpected Role of p-Toluenesulfonylmethyl Isocyanide as a Sulfonylating Agent in Reactions with α-Bromocarbonyl Compounds

The reactions of p-toluenesulfonylmethyl isocyanide (TosMIC) with α-bromocarbonyl compounds leading efficiently to α-sulfonated ketones, esters, and amides were reported, in which an explicit new role of TosMIC as the sulfonylating agent was uncovered for the first time. Mechanistic study by control experiments and DFT calculations suggested that the reaction is initiated by Cu(OTf)2-catalyzed hydration of TosMIC to form a formamide intermediate, which undergoes facile C-S bond cleavage under the mediation of a Cs2CO3 additive.

MONOAM1NE REUPTAKE INHIBITORS

The invention provides bupropion analogue compounds capable of inhibiting the reuptake of one or more monoamines. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine,and serotonin. Such compounds may be used to treat conditions that are responsive to inhibition of the reuptake of monoamines, including addiction, depression, and obesity

Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for cocaine addiction

A series of bupropion (1a) analogues (1b-1ff) were synthesized, and their in vitro and in vivo pharmacological properties evaluated with the goal of developing a 1a analogue that had better properties for treating addictions. Their in vitro pharmacological properties were examined by [3H] dopamine ([3H]DA), [3H]serotonin ([3H]5HT), and [3H]norepinephrine ([3H]NE) uptake inhibition studies, and by binding studies at the dopamine, serotonin, and norepinephrine transporters using [125I]RTI-55 in cloned transporters. Several analogues showed increased [3H]DAuptake inhibition with reduced or little change in [3H]5HT and [3H]NE uptake inhibition relative to bupropion. Thirty-five analogues were evaluated in a 1 h locomotor activity observation test and 32 in an 8 h locomotor activity observation test and compared to the locomotor activity of cocaine. Twenty-four analogues were evaluated for generalization to cocaine drug discrimination after i.p. administration, and twelve analogues were tested in a time course cocaine discrimination study using oral administration. 2-(N-Cyclopropylamino)-3- chloropropiophenone (1x) had the most favorable in vitro efficacy and in vivo pharmacological profile for an indirect dopamine agonist pharmacotherapy for treating cocaine, methamphetamine, nicotine, and other drugs of abuse addiction. 2009 American Chemical Society.

1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors

Dopamine, serotonin, and norepinephrine are essential for neurotransmission in the mammalian system. These three neurotransmitters have been the focus of considerable research because the modulation of their production and their interaction at monoamine receptors has profound effects upon a multitude of pharmacological outcomes. Our interest has focused on neurotransmitter reuptake mechanisms in a search for medications for cocaine abuse. Herein we describe the synthesis and biological evaluation of an array of 2-aminopentanophenones. This array has yielded selective inhibitors of the dopamine and norepinephrine transporters with little effect upon serotonin trafficking. A subset of compounds had no significant affinity at 5HT1A, 5HT1B, 5HT1C, D1, D2, or D3 receptors. The lead compound, racemic 1-(4-methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one 4a, was resolved into its enantiomers and the S isomer was found to be the most biologically active enantiomer. Among the most potent of these DAT/NET selective compounds are the 1-(3,4-dichlorophenyl)- (4u) and the 1-naphthyl- (4t) 2-pyrrolidin-1-yl-pentan-1-one analogues.

PYROVALERONE ANALOGS AND THERAPEUTIC USES THEREOF

New compounds that bind to monoamine transporters are described. The compounds of the present invention can be racemic or pure R-or S-enantiomers. Certain preferred compounds of the present invention have a high selectively dopamine transporter versus the serotonin transporter. Preferred monoamine transporters for the practice of the present invention include the dopamine transporter, the serotonin transporter and the norepinephrine transporter.