139502-80-0

Basic information

• Product Name: 4'-CHLOROBIPHENYL-3-CARBALDEHYDE
• Synonyms: AKOS BAR-0065;4'-CHLOROBIPHENYL-3-CARBALDEHYDE;4'-CHLORO[1,1'-BIPHENYL]-3-CARBALDEHYDE;4'-CHLORO[1,1'-BIPHENYL]-3-CARBOXALDEHYDE;3-(4-CHLOROPHENYL)BENZALDEHYDE;4'-Chloro-3-formylbiphenyl, 3-(4-Chlorophenyl)benzaldehyde;4'-Chloro-biphenyl-3-carboxaldehyde
• CAS NO: 139502-80-0
• Molecular Formula: C₁₃H₉ClO
• Molecular Weight: 216.66
• Product Categories: pharmacetical
• Mol File: 139502-80-0.mol

Chemical Properties

• Melting Point: 56-60 °C
• Boiling Point: 358.9 °C at 760 mmHg
• Flash Point: 185.6 °C
• Appearance: /
• Density: 1.214 g/cm³
• CAS DataBase Reference: 4'-CHLOROBIPHENYL-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-CHLOROBIPHENYL-3-CARBALDEHYDE(139502-80-0)
• EPA Substance Registry System: 4'-CHLOROBIPHENYL-3-CARBALDEHYDE(139502-80-0)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 22-36/37/38-51/53
• Safety Statements: 26-36/37-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 139502-80-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4'-Chlorobiphenyl-3-carbaldehyde is used as a key intermediate in the synthesis of various pharmaceutical and agrochemical compounds. Its unique chemical structure allows it to be a versatile building block for the development of new drugs and pesticides, contributing to advancements in healthcare and agriculture.
Used in Dye and Pigment Production:
In the dye and pigment industry, 4'-chlorobiphenyl-3-carbaldehyde is employed as an intermediate for the production of a wide range of dyes and pigments. Its chemical properties enable the creation of diverse colorants used in various applications, such as textiles, plastics, and printing inks.
Used in Specialty Chemicals Manufacturing:
4'-Chlorobiphenyl-3-carbaldehyde also finds application in the manufacturing of specialty chemicals, where its unique characteristics are leveraged to produce high-value products for specific industries. These may include the development of new materials with enhanced properties or the creation of novel chemical compounds for niche applications.

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 1679-18-1 4-Chlorophenylboronic acid 
• 1075-77-0 (E)-4-chlorocinnamic aldehyde 

Downstream Products

• 1201662-46-5 N-benzyl-3-chloro-5-(N-((4'-chlorobiphenyl-3-yl)methyl)-N-(4-fluorobenzyl)sulfamoyl)-4-hydroxybenzamide 
• 1201662-72-7 3-chloro-N-((4'-chlorobiphenyl-3-yl)methyl)-N-(4-fluorobenzyl)-2-hydroxy-5-(trifluoromethyl)benzenesulfonamide 
• 1201663-80-0 3-chloro-5-(N-((4'-chlorobiphenyl-3-yl)methyl)-N-(4-fluorobenzyl)sulfamoyl)-4-hydroxybenzoic acid 
• 1201663-82-2 3-chloro-5-(N-((4'-chlorobiphenyl-3-yl)methyl)-N-(4-fluorobenzyl)sulfamoyl)-4-hydroxybenzoyl chloride 
• 1201662-71-6 3,5-dichloro-N-((4'-chlorobiphenyl-3-yl)methyl)-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide 
• 1470061-22-3 C₂₀H₁₉ClO₂ 
• 1454860-39-9 C₂₇H₂₇ClO₄ 
• 1454860-37-7 C₂₆H₂₅ClO₄ 
• 1454861-12-1 C₂₀H₁₇ClO₂ 
• 1201663-79-7 1-(4'-chlorobiphenyl-3-yl)-N-(4-fluorobenzyl)methanamine 

Relevant articles and documents

Microwave-assisted organic acid-base-co-catalyzed tandem Meinwald rearrangement and annulation of styrylepoxides

A novel organic acid-base-co-catalyzed conversion of styrylepoxides into [1,1′-biaryl]-3-carbaldehydes was realized under microwave irradiation. Styrylepoxides first underwent an acid-catalyzed Meinwald rearrangement followed by a tandem base-catalyzed Michael addition, aldol addition, and aromatization sequence to generate [1,1′-biaryl]-3-carbaldehydes.

Palladium Palladium Nanoparticles Nanoparticles Supported Supported on β-cyclodextrin on β-Cyclodextrin Functionalised Functionalized Poly(amido Poly(amidoamine)s amine)s and their and Application Their Application in Suzuki-Miyaura in Suzuki-Miyaura Cross-Coupling Cross-Coupling Reactions Reactions

Herein, the synthesis, characterization and catalytic application of an organic-inorganic, palladium (Pd)-containing hybrid material, poly(amidoamine)-cyclodextrin (Pd@PAAs-CD), is reported as an efficient catalyst for Suzuki-Miyaura coupling reactions. The structure of Pd@PAAs-CD was confirmed by Fourier transform infrared spectroscopy (FTIR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), inductively-coupled plasma atomic emission spectroscopy (ICP-AES), and 1H nuclear magnetic resonance (NMR) spectroscopy. Furthermore, an efficient protocol has been developed using Pd@PAAs-CD as the catalyst in a Suzuki-Miyaura cross-coupling reaction in an aqueous medium in high yields. By using cyclodextrin (CD) as the mediator grafted onto PAAs, the Pd nanoparticles (NPs) were dispersed and enhanced the catalytic reaction by promoting host-guest interactions with the CD. In addition, the reusability of the Pd@PAAs-CD hybrid material is demonstrated for use in multiple sequential cross-coupling reactions.

Discovery of selective protein arginine methyltransferase 5 inhibitors and biological evaluations

Protein arginine methyltransferase 5 (PRMT5) is an important protein arginine methyltransferase that catalyzes the symmetric dimethylation of arginine resides on histones or non-histone substrate proteins. It has been thought as a promising target for many diseases, particularly cancer. Despite the potential applications of PRMT5 inhibitors in cancer treatment, very few of PRMT5i have been publicly reported. In this investigation, virtual screening and structure–activity relationship studies were carried out to discover novel PRMT5i, which finally led to the identification of a number of new PRMT5i. The most active compound, P5i-6, exhibited a considerable inhibitory potency against PRMT5 with an IC50 value of 0.57?μm, and a high selectivity for PRMT5 against other tested PRMTs. It displayed a very good antiviability activity against two colorectal cancer cell lines, HT-29 and DLD-1, and one hepatic cancer cell line, HepG2, in a sensitivity assay against 36 different cancer cell lines. Western blot assays indicated that P5i-6 selectively inhibited the symmetric dimethylations of H4R3 and H3R8 in DLD-1 cells. Overall, P5i-6 could be used as a chemical probe to investigate new functions of PRMT5 in biology and also served as a good lead compound for the development of new PRMT5-targeting therapeutic agents.

Probing the Azaaurone Scaffold against the Hepatic and Erythrocytic Stages of Malaria Parasites

The potential of azaaurones as dual-stage antimalarial agents was investigated by assessing the effect of a small library of azaaurones on the inhibition of liver and intraerythrocytic lifecycle stages of the malaria parasite. The whole series was screened against the blood stage of a chloroquine-resistant Plasmodium falciparum strain and the liver stage of P. berghei, yielding compounds with dual-stage activity and sub-micromolar potency against erythrocytic parasites. Studies with genetically modified parasites, using a phenotypic assay based on the P. falciparum Dd2-ScDHODH line, which expresses yeast dihydroorotate dehydrogenase (DHODH), showed that one of the azaaurone derivatives has the potential to inhibit the parasite mitochondrial electron-transport chain. The global urgency in finding new therapies for malaria, especially against the underexplored liver stage, associated with chemical tractability of azaaurones, warrants further development of this chemotype. Overall, these results emphasize the azaaurone chemotype as a promising scaffold for dual-stage antimalarials.

Synthesis and cross-coupling reactions of tetraalkylammonium organotrifluoroborate salts

Treatment of organoboronic acids with hydrofluoric acid generates an in situ tetracoordinate hydronium organotrifluoroborate species which undergoes counterion exchange with tetra-n-butylammonium hydroxide. The resultant tetraalkylammonium salts are as air and moisture stable as their potassium organotrifluoroborate counterparts with the added advantage of being readily soluble in organic media. They were found to undergo Pd-catalyzed Suzuki-Miyaura cross-couplings with a variety of aryl- and alkenylhalides under mild conditions. Their Pd-catalyzed cross-coupling with acid halides is also possible for the generation of ketones.

PHARMACOLOGICALLY ACTIVE TRIAZINONES

The compounds are substituted 1,2,4-triazin-5-ones which are histamine H 2-antagonists. Two specific compounds of the present invention are 3-2-(5-methyl-4-imidazolylmethylthio)ethylamino!-6-(3-methoxybenzyl)-1,2, 4-tr iazin-5-one and 3-2-(5-methyl-4-imidazolylmethylthio)ethylamino!-6-(3-pyridylmethyl)-1,2,4-tr iazin-5-one.