216443-25-3

Basic information

• Product Name: 3'-CHLORO-BIPHENYL-2-CARBALDEHYDE
• Synonyms: 3'-CHLORO-BIPHENYL-2-CARBALDEHYDE;3'-CHLORO[1,1'-BIPHENYL]-2-CARBALDEHYDE;3'-CHLORO-[1,1'-BIPHENYL]-2-CARBOXALDEHYDE;AKOS BAR-0182;2-chloro-6-phenylbenzaldehyde;3'-Chloro-biphenyl-2-carboxaldehyde
• CAS NO: 216443-25-3
• Molecular Formula: C₁₃H₉ClO
• Molecular Weight: 216.66
• EINECS: 200-589-5
• Mol File: 216443-25-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 363.5 °C at 760 mmHg
• Flash Point: 187.3 °C
• Appearance: /
• Density: 1.214g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3'-CHLORO-BIPHENYL-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-CHLORO-BIPHENYL-2-CARBALDEHYDE(216443-25-3)
• EPA Substance Registry System: 3'-CHLORO-BIPHENYL-2-CARBALDEHYDE(216443-25-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 216443-25-3(Hazardous Substances Data)

Usage

General Description

3'-Chloro-biphenyl-2-carbaldehyde is a chemical compound with the molecular formula C13H9ClO. It is a derivative of biphenyl, consisting of two benzene rings linked by a single carbon-carbon bond. The compound features a chloro group positioned at the third carbon atom of one of the benzene rings and an aldehyde functional group attached to the second carbon atom of the other benzene ring. It is commonly used as a building block in organic synthesis and pharmaceutical research. This chemical is known for its potential applications in the production of various organic compounds and materials due to its versatile reactivity and functional group compatibility. However, it is important to handle and use this compound with caution, as it may pose health and safety risks if not handled properly.

Upstream product

• 63503-60-6 3-chlorophenylboronic acid 
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• 36229-42-2 (3-chlorophenyl)magnesium bromide 
• 579-72-6 2-(dimethylamino)benzaldehyde 
• 108-37-2 1-bromo-3-chlorobenzene 
• 135-02-4 ortho-anisaldehyde 
• 93308-05-5 7-<3-Chlor-phenyl>-tropiliden 

Downstream Products

• 1292302-54-5 3-chloro-9-[(4-methylphenyl)sulfonylamino]fluorene 
• 1430810-73-3 1-(3'-chlorobiphenyl-2-ylmethyl)-4-(2-methoxyphenyl)piperazine 

Relevant articles and documents

Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement

Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.

Synthesis of dibenzopyranones and pyrazolobenzopyranones through copper(0)/Selectfluor system-catalyzed double C[sbnd]H activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes

A mild and efficient protocol for the synthesis of dibenzopyranones and pyrazolobenzopyranones was developed involving a copper(0)/Selectfluor system-catalyzed double C[sbnd]H activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes. Preliminary mechanistic studies suggest that both water and dioxygen act as the oxygen source in the formation of pyranone scaffolds.

Low-Valent, High-Spin Chromium-Catalyzed Cleavage of Aromatic Carbon-Nitrogen Bonds at Room Temperature: A Combined Experimental and Theoretical Study

The cleavage of aromatic carbon-nitrogen bonds catalyzed by transition metals is of high synthetic interest because such bonds are common in organic chemistry. However, few metal catalysts can be used to selectively break C(aryl)-N bonds in electronically neutral molecules. We report here the first low-valent, high-spin chromium-catalyzed cleavage of C(aryl)-N bonds in electronically neutral aniline derivatives at room temperature. By using simple and inexpensive chromium(II) chloride as precatalyst, accompanied by an imino auxiliary, the selective arylative and alkylative C-C coupling of C(aryl)-N bonds can be achieved. Crossover experiments indicate that a low-valent chromium species, formed in situ by reduction of CrCl2 with Grignard reagent, is responsible for the catalytic cleavage of C(aryl)-N bonds. DFT calculations show that facile insertion of the C(aryl)-N bond by chromium(0) can take place in a high-spin quintet (S = 2) ground state, whereas the lower-spin singlet (S = 0) and triplet (S = 1) states are inaccessible in energy. It was found that both donation of the sole paired d electrons in the d6 shell of high-spin chromium(0) to the antibonding orbital of the C(aryl)-N bond and the nitrogen ligating interaction to the metal center with its lone pair play important roles in the cleavage of the C(aryl)-N bond by the zerovalent chromium species.