5731-10-2

Basic information

• Product Name: 4'-FLUORO-BIPHENYL-4-CARBOXYLIC ACID
• Synonyms: 4-BIPHENYL-4'-FLUORO-CARBOXYLIC ACID;4'-FLUORO-1,1'-BIPHENYL-4-CARBOXYLIC ACID;4'-FLUORO-BIPHENYL-4-CARBOXYLIC ACID;4-(4-FLUOROPHENYL)BENZOIC ACID;AKOS BAR-0028;AKOS B025021;[1,1'-BIPHENYL]-4-CARBOXYLIC ACID, 4'-FLUORO-;CHEMBRDG-BB 4400446
• CAS NO: 5731-10-2
• Molecular Formula: C₁₃H₉FO₂
• Molecular Weight: 216.21
• Product Categories: Biphenyls;pharmacetical;C13 to C42+;Carbonyl Compounds;Carboxylic Acids
• Mol File: 5731-10-2.mol

Chemical Properties

• Melting Point: 235-240 °C
• Boiling Point: 369.4 °C at 760 mmHg
• Flash Point: 177.2 °C
• Appearance: /
• Density: 1.261 gcm/³
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.14±0.10(Predicted)
• CAS DataBase Reference: 4'-FLUORO-BIPHENYL-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-FLUORO-BIPHENYL-4-CARBOXYLIC ACID(5731-10-2)
• EPA Substance Registry System: 4'-FLUORO-BIPHENYL-4-CARBOXYLIC ACID(5731-10-2)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 22-36/37/38-51/53
• Safety Statements: 26-60-61
• WGK Germany: 2
• HazardClass: IRRITANT
• Hazardous Substances Data: 5731-10-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4'-Fluoro-biphenyl-4-carboxylic acid is used as a building block in organic synthesis for the creation of various organic molecules. Its unique structure allows for the development of new compounds with specific properties, contributing to the advancement of chemical research and innovation.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4'-Fluoro-biphenyl-4-carboxylic acid is utilized as a key intermediate in the synthesis of drugs. Its potential pharmacological properties make it a valuable component in the development of new medications, particularly those targeting specific therapeutic areas.
Used in Agrochemical Development:
4'-Fluoro-biphenyl-4-carboxylic acid also finds application in the agrochemical sector, where it serves as a precursor for the synthesis of agrochemicals. Its structure and properties are harnessed to develop compounds with pesticidal or herbicidal activities, enhancing crop protection and yield.
Used in Scientific Research:
The unique chemical and physical properties of 4'-Fluoro-biphenyl-4-carboxylic acid, particularly due to the presence of the fluorine atom, make it an important molecule for study in various scientific fields. Researchers explore its reactivity, stability, and interactions with other molecules to gain insights into its potential applications and to expand the understanding of fluorinated compounds.

Upstream product

• 124-38-9 carbon dioxide 
• 10540-37-1 4-fluoro-4'-iodo-1,1'-biphenyl 
• 350792-81-3 (ethyl)(difluoro)(4-fluorophenyl)silane 
• 586-76-5 4-Bromobenzoic acid 
• 1765-93-1 4-fluoroboronic acid 
• 619-67-0 4-Hydrazinobenzoic acid 
• 15290-29-6 4-(trimethylsilyl)benzoic acid 
• 225916-39-2 2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 456-22-4 4-Fluorobenzoic acid 
• 130387-74-5 4-fluorophenylmagnesium chloride 
• 98-80-6 phenylboronic acid 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 60992-98-5 4-(4-fluorophenyl)benzaldehyde 
• 74-11-3 para-chlorobenzoic acid 

Downstream Products

• 406233-14-5 N-(4'-fluorobiphenyl-4-carbonyl)-4-(2-hydroxyethylamino)-3-nitrobenzenesulfonamide 
• 51-17-2 benzoimidazole 
• 299206-66-9 2-[4-(4-fluorophenoxy)phenyl]-1H-benzimidazole 
• 1017952-43-0 4'-fluoro-biphenyl-4-carboxylic acid (6-dimethylaminomethyl-naphthalen-1-ylmethyl)-amide TFA salt 
• 913182-53-3 8-{[(4'-fluoro-biphenyl-4-carbonyl)-amino]-methyl}-quinoline-3-carboxylic acid ethyl ester 
• 1359844-10-2 2-(4’-fluoro-[1,1’-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

A general palladium-catalyzed cross-coupling of aryl fluorides and organotitanium (IV) reagents

Pd(OAc)2/1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxy-piperidine was demonstrated to effectively catalyze cross-coupling of aryl fluoride and aryl(alkyl) titanium reagent. Both electron-deficient and electron-rich aryl fluoride can react effectively with nucleophile and provide extensive functional groups tolerance. 2-Arylated product was realized by selective activation of the C–F bond. Graphic abstract: [Figure not available: see fulltext.].

Improving the metabolic stability of antifungal compounds based on a scaffold hopping strategy: Design, synthesis, and structure-activity relationship studies of dihydrooxazole derivatives

L-amino alcohol derivatives exhibited high antifungal activity, but the metabolic stability of human liver microsomes in vitro was poor, and the half-life of optimal compound 5 was less than 5 min. To improve the metabolic properties of the compounds, the scaffold hopping strategy was adopted and a series of antifungal compounds with a dihydrooxazole scaffold was designed and synthesized. Compounds A33-A38 substituted with 4-phenyl group on dihydrooxazole ring exhibited excellent antifungal activities against C. albicans, C. tropicalis and C. krusei, with MIC values in the range of 0.03–0.25 μg/mL. In addition, the metabolic stability of compounds A33 and A34 in human liver microsomes in vitro was improved significantly, with the half-life greater than 145 min and the half-life of 59.1 min, respectively. Moreover, pharmacokinetic studies in SD rats showed that A33 exhibited favourable pharmacokinetic properties, with a bioavailability of 77.69%, and half-life (intravenous administration) of 9.35 h, indicating that A33 is worthy of further study.

Green synthesis of biphenyl carboxylic acids via Suzuki–Miyaura cross-coupling catalyzed by a water-soluble fullerene-supported PdCl2 nanocatalyst

A green synthesis of variously substituted biphenyl carboxylic acids was achieved through Suzuki–Miyaura cross-coupling of a bromobenzoic acid with an aryl boronic acid using a water-soluble fullerene-supported PdCl2 nanocatalyst (C60-TEGs/ PdCl2). Yields of more than 90% were obtained at room temperature in 4 h using 0.05 mol% catalyst and 2 equiv. K2CO3.

Design, synthesis, and structure-activity relationship studies of L-amino alcohol derivatives as broad-spectrum antifungal agents

To discover broad spectrum antifungal agents, two strategies were applied, and a novel class of L-amino alcohol derivatives were designed and synthesized. 3-F substituted compounds 14i, 14n, 14s and 14v exhibited excellent antifungal activities with broad antifungal spectra against C. albicans and C. tropicalis, with MIC values in the range of 0.03–0.06 μg/mL, and against A. fumigatus and C. neoformans, with MIC values in the range of 1–2 μg/mL. Notably, Compounds 14i, 14n, 14s and 14v also displayed moderate activities against fluconazole-resistance strains 17# and CaR that were isolated from AIDS patients. Moreover, only compounds in the S-configuration showed antifungal activity. Preliminary mechanistic studies showed that the potent antifungal activity of compound 14v stemmed from inhibition of C. albicans CYP51. Compounds 14n and 14v were almost nontoxic to mammalian A549 cells, and their stability in human plasma was excellent.

Combating fluconazole-resistant fungi with novel β-azole-phenylacetone derivatives

A series of β-azole-phenylacetone derivatives with novel structures were designed and synthesized to combat the increasing incidence of susceptible fungal infections and drug-resistant fungal infections. The antifungal activity of the synthesized compounds was assessed against five susceptible strains and five fluconazole-resistant strains. Antifungal activity tests showed that most of the compounds exhibited excellent antifungal activities against five pathogenic strains with MIC values in the range of 0.03–1 μg/mL. Compounds with R1 = 3-F substituted and 15o and 15ae exhibited moderate antifungal activities against fluconazole-resistant strains 17# and CaR with MIC values in the range of 1–8 μg/mL. Compounds with R1 = H or 2-F (such as 15a, 15o, 15p) displayed moderate to good antifungal activity against fluconazole-resistant strains 632, 901 and 904 with MIC values in the range of 0.125–4 μg/mL. Notably, 15o and 15ae exhibited antifungal activity against five susceptible strains and five fluconazole-resistant strains. Preliminary mechanistic studies showed that the potent antifungal activity of compound 15ae stemmed from inhibition of C. albicans CYP51. Compounds 15o, 15z and 15ae were nearly nontoxic to mammalian A549 cells.

Method for synthesizing biphenylcarboxylic acid compound by using Suzuki coupling reaction

The invention provides a method for synthesizing a biphenylcarboxylic acid compound by using the Suzuki coupling reaction. According to the method, brominated aromatic hydrocarbon and arylboronic acidare used as raw materials, and water-soluble fullerene nanopalladium is used as a catalyst; and the equation of the Suzuki coupling reaction is as described in the specification. In the equation, R1and R2 represent substituents at different positions, may be acceptor or donor substituents, and may be monosubstitutents or polysubstitutent; and R1 and R2 may be identical or different groups. The water-soluble fullerene nanopalladium catalyst is cheap, easily available and environmentally friendly, and has high catalytic activity and stable properties. When the catalyst is used for catalysis ofthe Suzuki coupling reaction, conditions are mild, anhydrous anaerobic treatment and high-temperature treatment are not needed, and cost is low. The method can be applied to the industrial synthesisof non-steroidal anti-inflammatory drugs such as diphenylacetic acid and diflunisal.

Discovery of biphenyl imidazole derivatives as potent antifungal agents: Design, synthesis, and structure-activity relationship studies

Fungal infections have became a serious medical problem due to their high incidence and mortality. We describe the discovery and structure-activity relationships studies (SARs) of a series of novel biphenyl imidazole derivatives with excellent antifungal

Oxidation of aldehydes to carboxylic acids in water catalyzed by cobalt(II) Schiff-base complex anchored to SBA-15/MCM-41

Cobalt(II) Schiff-base complexes were successfully anchored to SBA-15/MCM-41 and used as a catalyst for the oxidation of aldehydes to afford carboxylic acids in water under the action of hydrogen peroxide. Reaction conditions, such as different catalyst type, reaction temperature, reaction time, solvents media, and catalyst amount were studied systematically. High yield (up to 98%) of the process was reached. Such substrate-supported catalyst can be reused up to five times without significant loss of its catalytic activity which is not lower than 85%.

A highly efficient catalyst of a nitrogen-based ligand for the Suzuki coupling reaction at room temperature under air in neat water

Glycine, as a kind of commercially available and inexpensive ligand, is used to prepare an air-stable and water-soluble catalyst for the Suzuki-Miyaura reaction in our study. In the presence of 0.1% [PdCl2(NH 2CH2COOH)2] as the catalyst, extremely excellent catalytic activity towards the Suzuki-Miyaura coupling of aryl halides containing the carboxyl group with various aryl boronic acids is observed at room temperature under air in neat water. the Partner Organisations 2014.