89901-02-0

Basic information

• Product Name: METHYL 4'-CHLORO[1,1'-BIPHENYL]-4-CARBOXYLATE
• Synonyms: RARECHEM AL BF 1239;METHYL 4'-CHLORO[1,1'-BIPHENYL]-4-CARBOXYLATE;AKOS BAR-0279;Methyl 4'-chlorobiphenyl-4-carboxylate, 95%;Methyl 4-(4-chlorophenyl)benzoate
• CAS NO: 89901-02-0
• Molecular Formula: C₁₄H₁₁ClO₂
• Molecular Weight: 246.69
• Mol File: 89901-02-0.mol

Chemical Properties

• Melting Point: 113-115°C
• Appearance: /
• CAS DataBase Reference: METHYL 4'-CHLORO[1,1'-BIPHENYL]-4-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4'-CHLORO[1,1'-BIPHENYL]-4-CARBOXYLATE(89901-02-0)
• EPA Substance Registry System: METHYL 4'-CHLORO[1,1'-BIPHENYL]-4-CARBOXYLATE(89901-02-0)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 89901-02-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
METHYL 4'-CHLORO[1,1'-BIPHENYL]-4-CARBOXYLATE is used as a key intermediate in the synthesis of various organic compounds, particularly in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatile structure allows for further functionalization and modification, making it a valuable building block in organic chemistry.
Used in Catalyst Preparation:
METHYL 4'-CHLORO[1,1'-BIPHENYL]-4-CARBOXYLATE is used as a precursor in the preparation of ionic compound-supported palladium complexes. These palladium complexes serve as efficient catalysts for the Suzuki-Miyaura coupling of aryl halides, a widely used cross-coupling reaction in organic synthesis. This reaction is particularly important for the formation of carbon-carbon bonds in the synthesis of biologically active molecules, pharmaceuticals, and advanced materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL 4'-CHLORO[1,1'-BIPHENYL]-4-CARBOXYLATE is used as a starting material for the synthesis of various drug candidates. Its unique structure and reactivity make it a promising candidate for the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
METHYL 4'-CHLORO[1,1'-BIPHENYL]-4-CARBOXYLATE is also used in the agrochemical industry for the synthesis of active ingredients in pesticides and herbicides. Its ability to form stable complexes with metal ions makes it a potential candidate for the development of new agrochemicals with enhanced efficacy and selectivity.

Upstream product

• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 1679-18-1 4-Chlorophenylboronic acid 
• 108-90-7 chlorobenzene 
• 1571-08-0 methyl 4-formylbenzoate 

Downstream Products

• 1595145-37-1 4-(4-{6-[(2S)-2-{[2-(4-cyanophenyl)ethyl]carbamoyl}azetidin-1-yl]-2-(trifluoromethyl)pyrimidin-4-yl}phenyl)benzoic acid 
• 1595145-35-9 (S)-methyl 4'-(6-(2-((4-cyanophenylethyl)carbamoyl)azetidin-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)-[1,1'-biphenyl]-4-carboxylate 
• 1381957-27-2 methyl 4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1’-biphenyl-4-carboxylate 
• 5748-41-4 4'-chlorobiphenyl-4-carboxylic acid 

Relevant articles and documents

para-Selective arylation and alkenylation of monosubstituted arenes using thianthreneS-oxide as a transient mediator

Using thianthreneS-oxide (TTSO) as a transient mediator,para-arylation and alkenylation of mono-substituted arenes have been demonstratedviaapara-selective thianthrenation/Pd-catalyzed thio-Suzuki-Miyaura coupling sequence under mild conditions. This reaction features a broad substrate scope, and functional group and heterocycle tolerance. The versatility of this approach was further demonstrated by late-stage functionalization of complex bioactive scaffolds, and direct synthesis of some pharmaceuticals, including Tetriprofen, Ibuprofen, Bifonazole, and LJ570.

Preparation method of para-substituted aryl compound

The invention discloses a preparation method of a para-substituted aryl compound shown as a formula (I) which is described in the specfication. The preparation method is characterized by comprising the following step of: subjecting an aryl sulfonium salt shown as a formula (II) which is described in the specfication and boride to a coupling reaction in a solvent in an inert atmosphere under the action of alkali and a palladium catalyst to obtain the para-substituted aryl compound. According to the method, mono-substituted aromatic hydrocarbon is taken as a substrate, the aryl sulfonium salt isconstructed in situ, and the palladium catalyst catalyzes the aryl sulfonium salt constructed in situ to undergo the Suzuki-Miyaura coupling reaction, so a mono-substituted aromatic hydrocarbon para-arylation or alkenylation product is constructed quickly and efficiently. The method is mild in conditions, high in substrate universality and wide in tolerance of a heterocyclic coupling substrate.

An Active Palladium Colloidal Catalyst for the Selective Oxidative Heterocoupling of (Hetero)Aryl Boronic Acids

A highly selective oxidative heterocoupling protocol for (hetero)aryl boronic acids with an active palladium colloidal catalyst was developed. The judicious choice of electronically different aryl boronic acids made possible such couplings under mild conditions, with air as oxidant, while embracing a wide substrate scope. This successful approach further allowed the development of a unique one-pot sequential oxidative heterocoupling/Suzuki–Miyaura cross-coupling tandem process for accessing substituted terphenyls.

Metal-free oxidative decarbonylative coupling of aromatic aldehydes with arenes: Direct access to biaryls

A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds was developed. This novel coupling was proposed to proceed via a non-chain radical homolytic aromatic substitution (HAS) type mechanism, based on the substrate scope, ortho-regioselectivity, radical trapping experiments and DFT calculation studies. With the ready availability of aromatic aldehydes and arenes, metal-free conditions should make this coupling attractive for the biaryl synthesis.