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2-BROMO-1-(4-CHLOROPHENYL)-2-PHENYLETHAN-1-ONE, commonly known as U-47700, is a synthetic opioid that has been recognized for its potent agonistic effects at the mu-opioid receptor. Structurally, it is related to other opioids such as fentanyl and AH-7921. Despite its ability to produce effects akin to prescription opioids like morphine and oxycodone, U-47700 is notorious for its high potential for abuse and the associated risks of overdose and death, leading to its classification as a Schedule I controlled substance in the United States and its ban in several other countries.

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  • 1889-78-7 Structure
  • Basic information

    1. Product Name: 2-BROMO-1-(4-CHLOROPHENYL)-2-PHENYLETHAN-1-ONE
    2. Synonyms: 2-BROMO-1-(4-CHLOROPHENYL)-2-PHENYLETHAN-1-ONE;2-BROMO-1-(4-CHLORO-PHENYL)-2-PHENYL-ETHANONE;2-Bromo-1-(4-chlorophenyl)-2-phenylethan-1-one, 95+%
    3. CAS NO:1889-78-7
    4. Molecular Formula: C14H10BrClO
    5. Molecular Weight: 309.59
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1889-78-7.mol
  • Chemical Properties

    1. Melting Point: 65 °C
    2. Boiling Point: 387.3°Cat760mmHg
    3. Flash Point: 188°C
    4. Appearance: /
    5. Density: 1.491g/cm3
    6. Vapor Pressure: 3.33E-06mmHg at 25°C
    7. Refractive Index: 1.625
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: 2-BROMO-1-(4-CHLOROPHENYL)-2-PHENYLETHAN-1-ONE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2-BROMO-1-(4-CHLOROPHENYL)-2-PHENYLETHAN-1-ONE(1889-78-7)
    12. EPA Substance Registry System: 2-BROMO-1-(4-CHLOROPHENYL)-2-PHENYLETHAN-1-ONE(1889-78-7)
  • Safety Data

    1. Hazard Codes:  C:Corrosive;
    2. Statements: 36/37/38
    3. Safety Statements: 26-36/37/39
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1889-78-7(Hazardous Substances Data)

1889-78-7 Usage

Uses

Used in Pharmaceutical Research:
2-BROMO-1-(4-CHLOROPHENYL)-2-PHENYLETHAN-1-ONE is used as a research chemical for understanding the mechanisms of opioid action and addiction. Its potent agonistic properties at the mu-opioid receptor make it a valuable tool in studying the effects and risks associated with opioid use.
Used in Drug Enforcement and Policy Making:
2-BROMO-1-(4-CHLOROPHENYL)-2-PHENYLETHAN-1-ONE is utilized in the development of drug testing methods and policies aimed at controlling the distribution and abuse of synthetic opioids. Its classification as a Schedule I controlled substance underscores the need for stringent regulations to prevent misuse and protect public health.
Used in Toxicology and Forensic Analysis:
In the field of toxicology and forensic science, 2-BROMO-1-(4-CHLOROPHENYL)-2-PHENYLETHAN-1-ONE is employed as a reference substance for the detection and analysis of synthetic opioids in biological samples. This aids in investigations related to drug-related fatalities and substance abuse cases.
Used in Addiction Treatment and Education:
2-BROMO-1-(4-CHLOROPHENYL)-2-PHENYLETHAN-1-ONE serves as a cautionary example in addiction treatment programs and educational initiatives, highlighting the dangers of synthetic opioids and the importance of responsible opioid use and management.

Check Digit Verification of cas no

The CAS Registry Mumber 1889-78-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,8 and 9 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1889-78:
(6*1)+(5*8)+(4*8)+(3*9)+(2*7)+(1*8)=127
127 % 10 = 7
So 1889-78-7 is a valid CAS Registry Number.
InChI:InChI=1/C14H10BrClO/c15-13(10-4-2-1-3-5-10)14(17)11-6-8-12(16)9-7-11/h1-9,13H

1889-78-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-bromo-1-(4-chlorophenyl)-2-phenylethanone

1.2 Other means of identification

Product number -
Other names 1-(4-chlorophenyl)-2-bromo-2-phenylethanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1889-78-7 SDS

1889-78-7Relevant articles and documents

Design, synthesis and biological evaluation of novel pyrrolidone-based derivatives as potent p53-MDM2 inhibitors

Si, Dongjuan,Luo, Huijuan,Zhang, Xiaomeng,Yang, Kundi,Wen, Hongmei,Li, Wei,Liu, Jian

, (2021/08/27)

Inhibition of the interactions of the tumor suppressor protein p53 with its negative regulators MDM2 in vitro and in vivo, representing a valuable therapeutic strategy for cancer treatment. The natural product chalcone exhibited moderate inhibitory activity against MDM2, thus based on the binding mode between chalcone and MDM2, a hit unsaturated pyrrolidone scaffold was obtained through virtual screening. Several unsaturated pyrrolidone derivatives were synthesized and biological evaluated. As a result, because the three critical hydrophobic pockets of MDM2 were occupied by the substituted-phenyl linked at the pyrrolidone fragment, compound 4 h demonstrated good binding affinity with the MDM2. Additionally, compound 4 h also showed excellent antitumor activity and selectivity, and no cytotoxicity against normal cells in vitro. The further antitumor mechanism studies were indicated that compound 4 h could successfully induce the activation of p53 and corresponding downstream p21 proteins, thus successfully causing HCT116 cell cycle arrest in the G1/M phase and apoptosis. Thus, the novel unsaturated pyrrolidone p53-MDM2 inhibitors could be developed as novel antitumor agents.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

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Paragraph 00630; 00631; 001837; 001840, (2021/01/22)

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 a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

3D-QSAR assisted identification of FABP4 inhibitors: An effective scaffold hopping analysis/QSAR evaluation

Floresta, Giuseppe,Cilibrizzi, Agostino,Abbate, Vincenzo,Spampinato, Ambra,Zagni, Chiara,Rescifina, Antonio

, p. 276 - 284 (2018/12/11)

Following on the recent publication of pharmacologically relevant effects, small molecule inhibitors of adipocyte fatty-acid binding protein 4 (FABP4) have attracted high interest. FABP4 is mainly expressed in macrophages and adipose tissue, where it regulates fatty acid storage and lipolysis, being also an important mediator of inflammation. In this regard, FABP4 recently demonstrated an interesting molecular target for the treatment of type 2 diabetes, other metabolic diseases and some type of cancers. In the past years, hundreds of effective FABP4 inhibitors have been synthesized. In this paper, a quantitative structure-activity relationship (QSAR) model has been produced, in order to predict the bioactivity of FABP4 inhibitors. The methodology has been combined with a scaffold-hopping approach, allowing to identify three new molecules that act as effective inhibitors of this protein. These molecules, synthesized and tested for their FABP4 inhibitor activity, showed IC50 values between 3.70 and 5.59 μM, with a high level of agreement with the predicted values.

Discovery of the First in Vivo Active Inhibitors of the Soluble Epoxide Hydrolase Phosphatase Domain

Kramer, Jan S.,Woltersdorf, Stefano,Duflot, Thomas,Hiesinger, Kerstin,Lillich, Felix F.,Kn?ll, Felix,Wittmann, Sandra K.,Klingler, Franca-M.,Brunst, Steffen,Chaikuad, Apirat,Morisseau, Christophe,Hammock, Bruce D.,Buccellati, Carola,Sala, Angelo,Rovati, G. Enrico,Leuillier, Matthieu,Fraineau, Sylvain,Rondeaux, Julie,Hernandez-Olmos, Victor,Heering, Jan,Merk, Daniel,Pogoryelov, Denys,Steinhilber, Dieter,Knapp, Stefan,Bellien, Jeremy,Proschak, Ewgenij

, p. 8443 - 8460 (2019/10/16)

The emerging pharmacological target soluble epoxide hydrolase (sEH) is a bifunctional enzyme exhibiting two different catalytic activities that are located in two distinct domains. Although the physiological role of the C-terminal hydrolase domain is well-investigated, little is known about its phosphatase activity, located in the N-terminal phosphatase domain of sEH (sEH-P). Herein we report the discovery and optimization of the first inhibitor of human and rat sEH-P that is applicable in vivo. X-ray structure analysis of the sEH phosphatase domain complexed with an inhibitor provides insights in the molecular basis of small-molecule sEH-P inhibition and helps to rationalize the structure-activity relationships. 4-(4-(3,4-Dichlorophenyl)-5-phenyloxazol-2-yl)butanoic acid (22b, SWE101) has an excellent pharmacokinetic and pharmacodynamic profile in rats and enables the investigation of the physiological and pathophysiological role of sEH-P in vivo.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

-

Paragraph 00672; 00673; 00674; 001879; 001880; 001883, (2019/07/17)

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 glycolate oxidase (GO). Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

Copper nitrate-catalyzed α -bromination of aryl ketones with hydrobromic acid

Wang, Jianqiang,Wang, Xiaolei,Niu, Zong-Qiang,Wang, Jian,Zhang, Man,Li, Jing-Hua

, p. 165 - 168 (2016/02/23)

An efficient method for α-bromination of aryl ketones, using the combination of molecular oxygen and aqueous hydrobromic acid as a brominating agent in the presence of the copper nitrate, has been developed. This catalytic system, which uses cheap and readily available reactants, shows good atom economy with water as the only by-product.

Synthesis, characterization, and in vitro antimicrobial activity of methyleneamine-linked bis-heterocycles

Babulreddy,Hymavathi,Hussain, Md. Manzoor,Narayana Swamy

, p. 727 - 733 (2013/06/27)

A new class of methyleneamine-linked bis-heterocycles that exhibit antimicrobial activity was synthesized. Bromination of 1 followed by condensation with thiourea gave 3. The reaction of 3 with propargyl bromide in dry toluene under inert atmosphere led t

Synthesis and antimicrobial activity of a new class of methyleneamine- linked bis-heterocycles

Reddy, A. Babul,Hymavathi,Chandrasekhar,Naveen,Swamy, G. Narayana

experimental part, p. 1175 - 1180 (2011/11/06)

A new class of methyleneamine-linked bis-heterocycles that exhibit antimicrobial activity was synthesized. Bromination of 1 followed by condensation with thiourea gave 3. The reaction of 3 with propargyl bromide in dry toluene under inert atmosphere led to the formation of 4. Its subsequent reaction with different aromatic azides 5 using CuSO4.5H 2O-sodiumascorbate system in a 2:1 mixture of water and tert-butylalcohol yielded the title compounds 6a-j in good yields. The identities of these compounds were confirmed following elemental analysis, IR, 1H, 13C NMR, and mass spectral studies. All the title compounds exhibited pronounced in vitro antibacterial and antifungal activities.

Novel bisaryl substituted thiazoles and oxazoles as highly potent and selective peroxisome proliferator-activated receptor δ agonists

Epple, Robert,Cow, Christopher,Xie, Yongping,Azimioara, Mihai,Russo, Ross,Wang, Xing,Wityak, John,Karanewsky, Donald S.,Tuntland, Tove,Nguyê?-Tran, Van T. B.,Ngo, Cara Cuc,Huang, David,Saez, Enrique,Spalding, Tracy,Gerken, Andrea,Iskandar, Maya,Seidel, H. Martin,Tian, Shin-Shay

experimental part, p. 77 - 105 (2010/04/30)

The discovery, synthesis, and optimization of compound 1 from a high-throughput screening hit to highly potent and selective peroxisome proliferator-activated receptor δ (PPARδ) agonists are reported. The synthesis and structure-activity relationship in this series are described in detail. On the basis of a general schematic PPAR pharmacophore model, scaffold 1 was divided into headgroup, linker, and tailgroup and successively optimized for PPAR activation using in vitro PPAR transactivation assays. A (2-methylphenoxy)acetic acid headgroup, a flexible linker, and a five-membered heteroaromatic center ring with two hydrophobic aryl substituents were required for efficient and selective PPARδ activation. The fine-tuning of these aryl substituents led to an array of highly potent and selective compounds such as compound 38c, displaying an excellent pharmacokinetic profile in mouse. In an in vivo acute dosing model, selected members of this array were shown to induce the expression of pyruvate dehydrogenase kinase-4 (PDK4) and uncoupling protein-3 (UCP3), genes that are known to be involved in energy homeostasis and regulated by PPARδ in skeletal muscle.

NOVEL IMIDAZO[1,2-a]PYRIDINE CANNABINOID RECEPTOR LIGANDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

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Page/Page column 38-39, (2008/06/13)

The present invention relates to novel imidazo[1,2-a]pyridine cannabinoid receptor ligands, in particular cannabinoid 1 (CB1) or cannabinoid 2 (CB2) receptor ligands, and uses thereof for treating diseases, conditions and/or disorders modulate by a cannab

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