13391-38-3

Usage

Structure

Substituted benzene ring with a chlorine atom and a bromine atom

Explanation

The compound has a benzene ring (a six-carbon ring with alternating single and double bonds) with a chlorine atom and a bromine atom attached at different positions.

Explanation

The chlorine and bromine atoms are the functional groups in 1-(α-Chlorobenzyl)-4-bromobenzene, which contribute to its unique reactivity and properties.

Explanation

The compound is used as a building block for creating more complex molecules in various fields, including the production of pharmaceuticals, agrochemicals, and other specialty chemicals.

Explanation

The presence of both chlorine and bromine atoms on the benzene ring gives 1-(α-Chlorobenzyl)-4-bromobenzene unique reactivity, making it valuable in a wide range of chemical applications.

Explanation

Most organic compounds with molecular weights around 300 or less are solids at room temperature. Although the exact melting point is not provided, it is reasonable to assume that 1-(α-Chlorobenzyl)-4-bromobenzene is a solid at room temperature.

Explanation

Compounds with halogenated aromatic rings, like 1-(α-Chlorobenzyl)-4-bromobenzene, are generally soluble in organic solvents such as dichloromethane, ethyl acetate, and acetone.

Explanation

The compound is likely stable under normal conditions, such as room temperature and pressure, as it is used in various chemical applications without any specific mention of instability.

Explanation

As with many chemicals, 1-(α-Chlorobenzyl)-4-bromobenzene may pose health risks if not handled properly. It is important to follow safety guidelines and use appropriate protective equipment when working with 1-(α-Chlorobenzyl)-4-bromobenzene.

Explanation

To maintain the stability and safety of the compound, it should be stored in a cool, dry, and well-ventilated area, away from potential sources of ignition, such as heat, sparks, and open flames.

Functional groups

Chlorine (Cl) and bromine (Br) atoms

Applications

Organic synthesis, chemical research, pharmaceuticals, agrochemicals, and specialty chemicals

Reactivity

Unique due to the presence of both chlorine and bromine atoms

Physical state

Likely a solid at room temperature

Solubility

Soluble in organic solvents

Stability

Stable under normal conditions

Hazards

Potential irritant, toxic, or harmful if inhaled, ingested, or absorbed through the skin

Storage

Store in a cool, dry, and well-ventilated area, away from heat, sparks, and open flames

InChI:InChI=1/C13H10BrCl/c14-12-8-6-11(7-9-12)13(15)10-4-2-1-3-5-10/h1-9,13H

Upstream product

• 29334-16-5 phenyl(4-bromophenyl)methanol 
• 1122-91-4 4-bromo-benzaldehyde 
• 90-90-4 (4-bromophenyl)(phenyl)methanone 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 124419-82-5 1,3-Bis(4-bromphenyl)-1,3-diphenyl-1-propen 
• 102374-42-5 4'-bromo-3α-(diphenylmethoxy)tropane 
• 308110-11-4 tert-butyl 4-[(4-bromophenyl)(phenyl)methyl]-1-piperazinecarboxylate 
• 22524-18-1 1,2-diphenyl-1,2-di-p-bromophenylethane 
• 68240-62-0 1-((4-bromophenyl)(phenyl)methyl)piperazine 
• 90-90-4 (4-bromophenyl)(phenyl)methanone 
• 2116-36-1 1-benzyl-4-bromo-benzene 
• 308110-12-5 tert-butyl 4-[[4-(2-ethylbutanoyl)phenyl](phenyl)methyl]-1-piperazinecarboxylate 
• 80272-20-4 3-(4-bromophenyl)-3-phenyl-propionic acid 
• 1221398-65-7 tropinone O-((4-bromophenyl)phenylmethyl)oxime 
• 1423701-90-9 C₂₁H₁₇BrO₂ 
• 21771-89-1 α-(4-bromophenyl)phenylacetic acid 
• 5359-48-8 methyl 2-(4-bromophenyl)-2-phenylacetate 
• 1423700-11-1 methyl 2-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 1‐(Diarylmethyl)‐1h‐1,2,4‐triazoles and 1‐(diarylmethyl)‐1h‐imidazoles as a novel class of anti‐mitotic agent for activity in breast cancer

We report the synthesis and biochemical evaluation of compounds that are designed as hybrids of the microtubule targeting benzophenone phenstatin and the aromatase inhibitor letrozole. A preliminary screening in estrogen receptor (ER)‐positive MCF‐7 breast cancer cells identified 5‐((2H‐1,2,3‐triazol‐1‐yl)(3,4,5‐trimethoxyphenyl)methyl)‐2‐methoxyphenol 24 as a potent antiproliferative compound with an IC50 value of 52 nM in MCF‐7 breast cancer cells (ER+/PR+) and 74 nM in triple‐negative MDA‐MB‐231 breast cancer cells. The compounds demonstrated significant G2/M phase cell cycle arrest and induction of apoptosis in the MCF‐7 cell line, inhibited tubulin polymerisation, and were selective for cancer cells when evaluated in non-tumorigenic MCF‐10A breast cells. The immunofluorescence staining of MCF‐7 cells confirmed that the compounds targeted tubulin and induced multinucleation, which is a recognised sign of mitotic catastrophe. Computational docking studies of compounds 19e, 21l, and 24 in the colchicine binding site of tubulin indicated potential binding conformations for the compounds. Compounds 19e and 21l were also shown to selectively inhibit aromatase. These compounds are promising candidates for development as antiproliferative, aromatase inhibitory, and microtubule‐disrupting agents for breast cancer.

Desulfurative Chlorination of Alkyl Phenyl Sulfides

The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)benzene (PhICl2) is reported. This mild and rapid nucleophilic chlorination is extended to sulfa-Michael derived sulfides, affording elimination-sensitive β-chloro carbonyl and nitro compounds in good yields. The chlorination of enantioenriched benzylic sulfides to the corresponding inverted chlorides proceeds with high stereospecificity, thus providing a formal entry into enantioenriched chloro-Michael adducts. A mechanism implying the formation of a dichloro-λ4-sulfurane intermediate is proposed.

Synthesis and Anticancer Activity of 1-(1H -Indol-3-yl)-2-(4-diarylmethylpiperazine-1-yl)ethane-1,2-dione Derivatives

Several new 1-(4-diarylmethylpiperazine-1-yl)-2-(1H-indol-3-yl)ethane-1,2-dione derivatives were synthesized by acylation of 1-diarylmethylpiperazine with 2-(1H-indol-3-yl)-2-oxoacetyl chloride. Their structures were confirmed by 1H NMR, IR, mass spectra, and elemental analysis. These compounds were further evaluated for their anticancer activity, and most of them were found to have moderate-to-potent antiproliferative activities against Hela, A-549, and ECA-109 cancer cell lines in vitro.

LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS

Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.

Discovery of novel and potent benzhydryl-tropane trypanocides highly selective for Trypanosoma cruzi

A benzhydryl tropinone oxime that is potently toxic to Trypanosoma cruzi has been previously identified. An SAR investigation determined that no part of the original compound was superfluous and all early SAR probes led to significant drops in activity. The only alteration that could be achieved without loss of activity was replacement of the aryl chloride substituent with chloro homologues. This led to the discovery of a trifluoromethyl-containing analogue with an EC50 against T. cruzi of 30 nM and a cytotoxicity selectivity index of over 1000 relative to rat skeletal myoblast L-6 cells.

Design, synthesis, and structure-activity relationships of pyrazolo[3,4-d]pyrimidines: A novel class of potent enterovirus inhibitors

A series of pyrazolo[3,4-d]pyrimidines were synthesized and their antiviral activity was evaluated in a plaque reduction assay. It is very interesting that this class of compounds provide remarkable evidence that they are very specific for human enteroviruses, in particular, coxsackieviruses. Some derivatives proved to be highly effective in inhibiting enterovirus replication at nanomolar concentrations. SAR studies revealed that the phenyl group at the N-1 position and the hydrophobic diarylmethyl group at the piperazine largely influenced the in vitro antienteroviral activity of this new class of potent antiviral agents. It was found that the pyrazolo[3,4-d]pyrimidines with a thiophene substituent, such as compounds 20-24, in general exhibited high activity against coxsackievirus B3 (IC50=0.063-0.089μM) and moderate activity against enterovirus 71 (IC50=0.32-0.65μM) with no apparent cytotoxic effect toward RD (rhabdomyosarcoma) cell lines (CC5025μ M).

New diarylmethylpiperazines as potent and selective nonpeptidic δ opioid receptor agonists with increased in vitro metabolic stability

Nonpeptide δ opioid agonists are analgesics with a potentially improved side-effect and abuse liability profile, compared to classical opioids. Andrews analysis of the NIH nonpeptide lead SNC-80 suggested the removal of substituents not predicted to contribute to binding. This approach led to a simplified lead, N,N-diethyl-4-[phenyl(1-piperazinyl)methyl]benzamide (1), which retained potent binding affinity and selectivity to the human δ receptor (IC50 = 11 nM, μ/δ = 740, κ/δ > 900) and potency as a full agonist (EC50 = 36 nM) but had a markedly reduced molecular weight, only one chiral center, and increased in vitro metabolic stability. From this lead, the key pharmacophore groups for δ receptor affinity and activation were more clearly defined by SAR and mutagenesis studies. Further structural modifications on the basis of 1 confirmed the importance of the N,N-diethylbenzamide group and the piperazine lower basic nitrogen for δ binding, in agreement with mutagenesis data. A number of piperazine N-alkyl substituents were tolerated. In contrast, modifications of the phenyl group led to the discovery of a series of diarylmethylpiperazines exemplified by N,N-diethyl-4-[1-piperazinyl(8-quinolinyl)-methyl]benzamide (56) which had an improved in vitro binding profile (IC50 = 0.5 nM, μ/δ = 1239, EC50 = 3.6 nM) and increased in vitro metabolic stability compared to SNC-80.

Novel 4'-Substituted and 4',4"-Disubstituted 3α-(Diphenylmethoxy)tropane Analogs as Potent and Selective Dopamine Uptake Inhibitors

A series of 4'-substituted and 4',4"-disubstituted 3α-(diphenylmethoxy)tropane analogs were prepared as novel probes for the dopamine transporter.These compounds were evaluated in radiolabeled binding assays for the dopamine, norepinephrine, and serotonin transporters.All of these compounds monophasically displaced WIN 35,428 binding in rat caudate putamen with Ki values ranging from 11.8 to 2000 nM.The most potent compound in this series was 4',4"-difluoro 3α-(diphenylmethoxy)tropane 7c with Ki=11.8 nM.All of the compounds inhibited dopamine uptake in rat caudate putamen (IC50 = 24-4456 nM) which correlated significantly (r = 0.907; p > 0.0001) with binding affinities at the dopamine transporter.None of the compounds demonstrated high-affinity binding at the norepinephrine (Ki > 4800 nM) or serotonin (Ki > 690 nM)transporters.Therefore, the most potent dopamine uptake inhibitors in this series were highly selective for the dopamine transporter.Preliminary behavioral studies of several of these analogs (7a-e) suggested that the compounds did not display a cocaine-like behavioral profile, despite their ability to inhibit dopamine uptake.The present data coupled with the 3α-(diphenylmethoxy)tropane analogs may be interacting at a different active site than cocaine on the dopamine transporter and that an additional binding domain might be exploited for the identification of potential therapeutics for the treatment of cocaine abuse.