76650-08-3

Basic information

• Product Name: 2-BROMO-1-(3-BROMOPHENYL)-1-PROPANONE
• Synonyms: 2-BROMO-1-(3-BROMOPHENYL)-1-PROPANONE;2-BROMO-1-(3-BROMOPHENYL)-PROPAN-1-ONE;Bupropion Impurity 16
• CAS NO: 76650-08-3
• Molecular Formula: C₉H₈Br₂O
• Molecular Weight: 291.97
• Product Categories: Aromatic Ketones (substituted)
• Mol File: 76650-08-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-BROMO-1-(3-BROMOPHENYL)-1-PROPANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-1-(3-BROMOPHENYL)-1-PROPANONE(76650-08-3)
• EPA Substance Registry System: 2-BROMO-1-(3-BROMOPHENYL)-1-PROPANONE(76650-08-3)

Safety Data

• Hazardous Substances Data: 76650-08-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-BROMO-1-(3-BROMOPHENYL)-1-PROPANONE is used as an intermediate for the production of various pharmaceuticals. Its unique structure allows it to be a building block in the creation of organic molecules that can be further utilized in the development of new drugs.
Used in Organic Compound Synthesis:
In the field of organic chemistry, 2-BROMO-1-(3-BROMOPHENYL)-1-PROPANONE serves as a key intermediate, enabling the synthesis of a wide range of organic compounds. Its reactivity and structural features make it a valuable component in the formation of complex organic molecules.
Used in Research and Development:
2-BROMO-1-(3-BROMOPHENYL)-1-PROPANONE is also employed in the research and development of new drugs and chemicals. Its versatility and reactivity contribute to the exploration of novel chemical reactions and the discovery of innovative applications in various industries.
Safety Considerations:
It is important to handle 2-BROMO-1-(3-BROMOPHENYL)-1-PROPANONE with care, as it is considered a hazardous material. Its use should be confined to controlled laboratory settings to ensure the safety of researchers and the environment.

Upstream product

• 19829-31-3 1-(3-bromophenyl)-1-propanone 
• 6952-59-6 3-cyanobromobenzene 

Downstream Products

• 76650-09-4 1-(3-Bromo-phenyl)-2-fluoro-propan-1-one 
• 454464-60-9 5-(3-bromo-phenyl)-1-(3-chloro-phenylamino)-4-methyl-1H-imidazole-2-thiol 
• 76650-10-7 2-Bromo-1-(3-bromo-phenyl)-2-fluoro-propan-1-one 
• 842155-44-6 acetic acid 2-(3-bromo-phenyl)-1-methyl-2-oxo-ethyl ester 
• 1049974-35-7 2-(N-tert-butylamino)-3'-bromopropiophenone 
• 1214940-00-7 3′-bromo-α-pyrrolidinopropiophenone 
• 1214939-95-3 2-(N-cyclopentylamino)-3'-bromopropiophenone 
• 1321959-93-6 4-(3-bromophenyl)-5-methyl-N-(4-methylpyridin-2-yl)thiazol-2-amine 
• 19829-31-3 1-(3-bromophenyl)-1-propanone 

Relevant articles and documents

α-PPP and its derivatives are selective partial releasers at the human norepinephrine transporter: A pharmacological characterization of interactions between pyrrolidinopropiophenones and uptake1 and uptake2 monoamine transporters

While classical cathinones, such as methcathinone, have been shown to be monoamine releasing agents at human monoamine transporters, the subgroup of α-pyrrolidinophenones has thus far solely been characterized as monoamine transporter reuptake inhibitors. Herein, we report data from previously undescribed α-pyrrolidinopropiophenone (α-PPP) derivatives and compare them with the pharmacologically well-researched α-PVP (α-pyrrolidinovalerophenone). Radiotracer-based in vitro uptake inhibition assays in HEK293 cells show that the investigated α-PPP derivatives inhibit the human high-affinity transporters of dopamine (hDAT) and norepinephrine (hNET) in the low micromolar range, with α-PVP being ten times more potent. Similar to α-PVP, no relevant pharmacological activity was found at the human serotonin transporter (hSERT). Unexpectedly, radiotracer-based in vitro release assays reveal α-PPP, MDPPP and 3Br-PPP, but not α-PVP, to be partial releasing agents at hNET (EC50 values in the low micromolar range). Furthermore, uptake inhibition assays at low-affinity monoamine transporters, i.e., the human organic cation transporters (hOCT) 1–3 and human plasma membrane monoamine transporter (hPMAT), bring to light that all compounds inhibit hOCT1 and 2 (IC50 values in the low micromolar range) while less potently interacting with hPMAT and hOCT3. In conclusion, this study describes (i) three new hybrid compounds that efficaciously block hDAT while being partial releasers at hNET, and (ii) highlights the interactions of α-PPP-derivatives with low-affinity monoamine transporters, giving impetus to further studies investigating the interaction of drugs of abuse with OCT1-3 and PMAT.

SUBSTITUTED CYANOPYRROLIDINES WITH ACTIVITY AS USP30 INHIBITORS

The present invention relates to a class of substituted-cyanopyrrolidines with activity as inhibitors of the deubiquitylating enzyme USP30, having utility in a variety of therapeutic areas, including conditions involving mitochondrial dysfunction, cancer

Synthesis of α,β-dibromo ketones by photolysis of α-bromo ketones with N-bromosuccinimide: Photoinduced β-bromination of α-bromo ketones

Irradiation of α-bromopropiophenones in the presence of NBS results in the formation of α,β-dibromopropiophenones, which can be viewed as β-bromination of α-bromopropiophenones. The reaction is believed to go through a series of reactions; photoinduced C–Br bond cleavage, elimination of HBr to give α,β-unsaturated ketone intermediates, and addition of Br2, which are formed by the reaction between HBr and NBS. From mechanistic studies of the reaction, we have also found a very convenient method for α-debromination of the α,β-dibromopropiophenones which is by simple irradiation of the dibromo ketones in acetone or 2-propanol without the use of any additives. Our results demonstrate that bromine can be added into or eliminated from the alpha, beta, or both positions to the carbonyl group by photochemical methods, which make synthetic options of bromine containing carbonyl compounds versatile.

Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones

Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.

Enantioselective and Diastereoselective Construction of Chiral Amino Alcohols by Iridium-f-Amphox-Catalyzed Asymmetric Hydrogenation via Dynamic Kinetic Resolution

The iridium-f-amphox-catalyzed asymmetric hydrogenation of racemic α-amino β-unfunctionalized ketones proceeds via a DKR (dynamic kinetic resolution) process for the construction of various chiral N,N-disubstituted α-amino β-unfunctionalized alcohols in quantitative yields with excellent enantioselectivities and diastereoselectivities (all products >99% ee and >99:1 dr, TON up to 100 000). Importantly, this catalytic asymmetric hydrogenation with a DKR process provided a highly efficient and powerful synthetic strategy for the preparation of key chiral intermediates of the preclinical antitumor agent (S,S)-R116010.

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

Copper-catalyzed 1,2-addition of α-carbonyl iodides to alkynes

β,γ-Unsaturated ketones are an important class of organic molecules. Herein, copper catalysis has been developed for the synthesis of β-γ-unsaturated ketones through 1,2-addition of α-carbonyl iodides to alkynes. The reactions exhibit wide substrate scope and high functional group tolerance. The reaction products are versatile synthetic intermediates to complex small molecules. The method was applied for the formal synthesis of (±)-trichostatin A, a histone deacetylase inhibitor.

Hybrid dopamine uptake blocker-serotonin releaser ligands: A new twist on transporter-focused therapeutics

As part of our program to study neurotransmitter releasers, we report herein a class of hybrid dopamine reuptake inhibitors that display serotonin releasing activity. Hybrid compounds are interesting since they increase the design potential of transporter related compounds and hence represent a novel and unexplored strategy for therapeutic drug discovery. A series of N-alkylpropiophenones was synthesized and assessed for uptake inhibition and release activity using rat brain synaptosomes. Substitution on the aromatic ring yielded compounds that maintained hybrid activity, with the two disubstituted analogues (PAL-787 and PAL-820) having the most potent hybrid activity.

Substituted 2-aminothiazoles are exceptional inhibitors of neuronal degeneration in tau-driven models of Alzheimer's disease

A novel series of 2-aminothiazoles with strong protection in an Alzheimer's disease (AD) model comprising tau-induced neuronal toxicity is disclosed. These derivatives can be synthesized in one-pot and a small SAR of the substitution within these series afforded several compounds that counteracted tau-induced cell toxicity at nanomolar concentrations. These congeners therefore have strong potential as possible treatment for Alzheimer's disease and other related tauopathies.

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