5000-66-8

Basic information

• Product Name: 2-Bromo-2'-chloroacetophenone
• Synonyms: 2-Bromo-1-(-2-chlorophenyl)ethanone;-Bromo-2-chloroacetophenone;2'-CHLOROPHENACYL BROMIDE;2-CHLOROPHENACYL BROMIDE;2-BROMO-1-(2-CHLOROPHENYL)-1-ETHANONE;2-BROMO-1-(2-CHLOROPHENYL)ETHAN-1-ONE;2-BROMO-2'-CHLORO ACETOPHENONE;2'-CHLORO-2-BROMOACETOPHENONE
• CAS NO: 5000-66-8
• Molecular Formula: C₈H₆BrClO
• Molecular Weight: 233.49
• Product Categories: Aromatics;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 5000-66-8.mol
• Article Data: 66

Chemical Properties

• Boiling Point: 105 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 1.602 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5900(lit.)
• Storage Temp.: Keep Cold
• Solubility: Acetone, Chloroform, Ethyl Acetate, Methanol
• Sensitive: Lachrymatory
• CAS DataBase Reference: 2-Bromo-2'-chloroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-2'-chloroacetophenone(5000-66-8)
• EPA Substance Registry System: 2-Bromo-2'-chloroacetophenone(5000-66-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2922 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 5000-66-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Bromo-2'-chloroacetophenone is used as a synthetic intermediate for the production of various organic compounds. Its unique structure with both bromine and chlorine atoms allows for a range of chemical reactions, making it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Bromo-2'-chloroacetophenone is used as a key intermediate in the synthesis of certain drugs. Its reactive bromine and chlorine atoms can be utilized to form new bonds with other molecules, leading to the development of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Agrochemical Industry:
2-Bromo-2'-chloroacetophenone also finds application in the agrochemical industry, where it is used as a starting material for the synthesis of various pesticides and other crop protection agents. Its chemical properties enable the creation of compounds with targeted pest control capabilities, contributing to improved agricultural productivity and crop protection.
Used in Chemical Research:
In the field of chemical research, 2-Bromo-2'-chloroacetophenone serves as a valuable compound for studying various reaction mechanisms and exploring new synthetic pathways. Its unique structure provides researchers with opportunities to investigate the effects of bromine and chlorine substitution on the reactivity and selectivity of acetophenone derivatives, furthering the understanding of organic chemistry principles.

Upstream product

• 108-90-7 chlorobenzene 
• 13524-04-4 2'-chloro-sec-phenethyl alcohol 
• 2039-87-4 2-chlorostyrene 
• 577-16-2 2-Methylacetophenone 
• 873-31-4 2-chlorophenylacetylene 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 17356-08-0 thiourea 
• 1056775-36-0 1-(bromoethynyl)-2-chlorobenzene 
• 186581-53-3 diazomethane 
• 609-65-4 o-chlorobenzoyl chloride 

Downstream Products

• 16815-58-0 3-(N-2-Hydroxy-2-o-chlor-phenylaethyl-N-aethyl)amino-3-methyl-but-1-in 
• 18381-75-4 N-(2-Chlorphenacyl)cyclopropylamin 
• 34356-83-7 2,2‐dibromo‐1‐(2‐chlorophenyl)ethan‐1‐one 
• 1010835-95-6 2-tert-butyl-4-(2-chlorophenyl)-1H-imidazole 
• 1189020-53-8 S-[2-(2-chlorophenyl)-2-oxoethyl]-2-aminobenzenecarbothioate 
• 1220284-47-8 6,7-dichloro-2-(2-chlorophenyl)quinoxaline 
• 1220284-44-5 6,7-dimethyl-2-(2-chlorophenyl)quinoxaline 
• 1084-80-6 2-(2-chlorophenyl)quinoxaline 
• 1000775-20-1 1-(2-chlorophenyl)-2-[2-(2-chlorophenyl)-2-oxo-ethylsulfanyl]-ethanone 
• 1472613-49-2 ((2R,3S)-3-phenyl-3,4-dihydro-2H-thiopyran-2,6-diyl)bis((2-chlorophenyl)methanone) 
• 1429341-36-5 3-(2-chlorophenyl)-7-(5-methyl-2-(pyridin-3-yl)thiazol-4-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine 
• 1429341-34-3 3-(2-chlorophenyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine 
• 1418009-66-1 2-(2-((2-chloro-8-methylquinolin-3-yl)methylene)hydrazinyl)-4-(2-chlorophenyl)thiazole 
• 1311291-96-9 3-(2-chlorophenyl)-2H-benzo[b][1,4]oxazine 

Relevant articles and documents

Tulobuterol crystal form and preparation method thereof

The invention provides a tulobuterol crystal form and a preparation method thereof. The preparation method comprises the following steps of: dissolving tulobuterol in ethyl acetate and other good solvents, dropwisely adding n-heptane and other poor solvents into the system, filtering, taking the filter cake, and drying the filter cake to obtain the tulobuterol crystal form crystal. The crystal form is high in purity and good in stability, has superiority in process production, and is suitable for long-term storage in the preparation process.

Synthesis and anti-methicillin-resistant Staphylococcus aureus activity of 5,7-dibromo-2-benzoylbenzofurans alone and in combination with antibiotics

A series of 5,7-dibromo-2-benzoylbenzofurans were synthesized by the Rap–Stoermer condensation of 5,7-dibromosalicylaldehyde with diverse phenacyl bromides and evaluated for in-vitro antibacterial activities against methicillin-sensitive Staphylococcus aureus (MSSA) ATCC 29213, methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300, and MRSA ATCC 33591 by agar dilution method. The synergistic effects were determined by using the agar dilution checkerboard assay. The derivatives bearing carboxylic acid functional groups exhibited reasonable activity against MRSA strains with the best MIC = 32 μg/mL (9b, 9d). Moreover, the additive or synergistic interactions against MRSA strains was observed in six combinations (1b + cefuroxime/gentamicin, 1c + ciprofloxacin/gentamicin, 9b + gentamicin, and 9c + ciprofloxacin) with the fractional inhibitory concentration index (FICI) values in the range of 0.375–1.0. Significantly, the MICs of these antibiotics were reduced 2–4-fold. The results of the MTT assay illustrated the low mammalian cell cytotoxicity of these potent compounds.

Novel BuChE-IDO1 inhibitors from sertaconazole: Virtual screening, chemical optimization and molecular modeling studies

In our effort towards the identification of novel BuChE-IDO1 dual-targeted inhibitor for the treatment of Alzheimer's disease (AD), sertaconazole was identified through a combination of structure-based virtual screening followed by MM-GBSA rescoring. Preliminary chemical optimization was performed to develop more potent and selective sertaconazole analogues. In consideration of the selectivity and the inhibitory activity against target proteins, compounds 5c and 5d were selected for the next study. Further modification of compound 5c led to the generation of compound 10g with notably improved selectivity towards BuChE versus AChE. The present study provided us with a good starting point to further design potent and selective BuChE-IDO1 inhibitors, which may benefit the treatment of late stage AD.

Design and synthesis of 7-O-1,2,3-triazole hesperetin derivatives to relieve inflammation of acute liver injury in mice

Based on the previous research results of our research group, to further improve the anti-inflammatory activity of hesperetin, we substituted triazole at the 7-OH branch of hesperetin. We also evaluated the anti-inflammatory activity of 39 new hesperetin derivatives. All compounds showed inhibitory effects on nitric oxide (NO) and inflammatory factors in lipopolysaccharide-induced RAW264.7 cells. Compound d5 showed a strong inhibitory effect on NO (half maximal inhibitory concentration = 2.34 ± 0.7 μM) and tumor necrosis factor-α, interleukin (IL)-1β, and (IL-6). Structure–activity relationships indicate that 7-O-triazole is buried in a medium-sized hydrophobic cavity that binds to the receptor. Compound d5 can also reduce the reactive oxygen species production and significantly inhibit the expression of inducible NO synthase and cyclooxygenase-2 through the nuclear factor-κB signaling pathway. In vivo results indicate that d5 can reduce liver inflammation in mice with acute liver injury (ALI) induced by CCI4. In conclusion, d5 may be a candidate drug for treating inflammation associated with ALI.

Ru-Tethered (R,R)-TsDPEN with DMAB as an efficient catalytic system for high enantioselective one-pot synthesis of chiral β-aminolviaasymmetric transfer hydrogenation

This work reflects Ru-tethered-TsDPEN as an active chiral catalyst for one pot selective synthesis of optically active α-substituted alcohols and its derivatives from α-bromo ketones in the presence of dimethylamine borane (DMAB) as the hydrogen source. Various Ru-chiral catalysts have been screened and the methodology proceededviaa (R,R) Ru-tethered TsDPEN catalyst through asymmetric transfer hydrogenation (ATH) of the in-situ formed ketones to the corresponding chiral β-aminol product. Thus, the Ru-tethered TsDPEN-DMAB catalytic system works efficiently with higher yield and high enantiomeric excess over others for the ATH process. Based on a study ofortho,metaandparasubstituted α-bromo acetophenone derivatives, effective enantioselectivity has been observed fororthosubstituted β-aminol. The mechanism has been optimized depending on product analysis with the help of its kinetic AT-IR study. This work also focusses on the synthesis of various β-amino alcohol derivatives where the effect of an EWG and EDG on enantio-selectivity has been studied.

An umpolung oxa-[2,3] sigmatropic rearrangement employing arynes for the synthesis of functionalized enol ethers

An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C=O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic studies rule out the possibility of Pummerer-type rearrangement operating in this case.

BuChE-IDO1 inhibitor as well as preparation method and application thereof

The invention relates to the field of medicines, and particularly discloses a BuChE-IDO1 inhibitor as well as a preparation method and application thereof. The 7-chlorine-3-substituted benzothiophene part of sertaconazole is chemically modified, the influence of the 7-chlorine-3-substituted benzothiophene part of sertaconazole on the in-vitro inhibitory activity of AChE, BuChE and IDO1 is explored, the target compound is further optimized, and the technical problems that an existing BuChE-IDO1 inhibitor is poor in pertinence and safety are solved. What is explored is that an appropriate substituent group introduced to a 2-benzothiazole ring can form additional interaction with surrounding amino acids and heme iron, so that the binding affinity of the analogue with BuChE and IDO1 is increased, and a new idea is broadened for more efficient and targeted treatment of advanced AD diseases.

Chiral Bidentate Phosphoramidite-Pd Catalyzed Asymmetric Decarboxylative Dipolar Cycloaddition for Multistereogenic Tetrahydrofurans with Cyclic N-Sulfonyl Ketimine Moieties

An asymmetric [3 + 2] cycloaddition of vinyl ethylenecarbonates (VECs) and (E)-3-arylvinyl substituted benzo[d] isothiazole 1,1-dioxides has been developed using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst, providing a wide variety of chiral multistereogenic vinyltetrahydrofurans in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).

Facile Synthesis of α-Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source

An operationally simple and safe synthesis of α-haloketones using KBr and KCl as nonhazardous halogen sources is reported. It involves an iron-catalysed reaction of alkenes with KBr/KCl using O2 as terminal oxidant under the irradiation of visible-light. This strategy avoids the risks associated with handling halo-contained electrophiles (Cl2, Br2, NCS, NBS). The process is tolerant to several functional groups, and extended to a range of substituted styrenes in up to 89% yield. A radical reaction pathway is proposed based on control experiments and spectroscopy studies.

Microwave-assisted synthesis and luminescent activity of imidazo[1,2-a]pyridine derivatives

In this work, a series of phenacyl bromide derivatives was synthesized and employed as key intermediate for the synthesis of substituted imidazo[1,2-a]pyridines. First, phenacyl bromide molecules were obtained from the bromination reaction of acetophenones assisted by microwave irradiation, obtaining the products 4a-v in a 15 minutes reaction with yields in the range of 50% to 99%. Subsequently, the conjugation of these molecules with 2-aminopyridine conduced to the production of imidazo[1,2-a]pyridine derivatives (7a-v) in a 60-second reaction with yields of 24% to 99%. Improved yields were determined with respect to those obtained with more tedious methodologies like thermally and mechanically assisted routes. Intense luminescence emissions in the purple and blue regions of the electromagnetic spectra were observed under UV excitation according to the nature of the substituents. This environmentally friendly methodology is expected to constitute an important class of organic compounds for the development of biomarkers, photochemical sensors, and medicinal applications.