137045-30-8

Basic information

• Product Name: 3-FLUORO-4-BIPHENYLCARBOXYLIC ACID
• Synonyms: 3-FLUORO-4-BIPHENYLCARBOXYLIC ACID;2-Fluorobiphenyl-4-carboxylic acid 97%;FlurBiprofen impurity 5;Flurbiprofen EP Impurity E;3-fluoro-4-phenylbenzoic acid
• CAS NO: 137045-30-8
• Molecular Formula: C₁₃H₉FO₂
• Molecular Weight: 216.21
• Product Categories: C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 137045-30-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 223-227 °C(lit.)
• Boiling Point: 366.3°C at 760 mmHg
• Flash Point: 175.3°C
• Appearance: /
• Density: 1.261g/cm³
• Vapor Pressure: 5.21E-06mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 3.85±0.10(Predicted)
• CAS DataBase Reference: 3-FLUORO-4-BIPHENYLCARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-FLUORO-4-BIPHENYLCARBOXYLIC ACID(137045-30-8)
• EPA Substance Registry System: 3-FLUORO-4-BIPHENYLCARBOXYLIC ACID(137045-30-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 137045-30-8(Hazardous Substances Data)

Usage

Uses

2-Fluorobiphenyl-4-carboxylic Acid is an impurity of Flurbiprofen (F598700), an anti-inflammatory used as an analgesic. Flurbiprofen impurity E.

InChI:InChI=1/C13H9FO2/c14-12-8-10(6-7-11(12)13(15)16)9-4-2-1-3-5-9/h1-8H,(H,15,16)

Upstream product

• 41604-19-7 1-bromo-3-fluoro-4-phenylbenzene 
• 153556-42-4 4-bromo-3-fluorobenzoic acid 
• 98-80-6 phenylboronic acid 
• 124-38-9 carbon dioxide 
• 584-08-7 potassium carbonate 

Downstream Products

• 1093214-80-2 4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]phenylmethanol 
• 1093214-81-3 2-fluorobiphenyl-4-carboxylic acid[hydroxyimino(4-hydroxymethylphenyl)methyl]amide 
• 1093214-90-4 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(piperidine-1-ylcarbamoyl)piperidine-4-carboxylic acid benzyl ester 
• 1093214-71-1 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester (2,2-dimethylpropanoyloxymethyl) ester 
• 1093212-96-4 1-{4-[5-(2-fluorobiphenyl-4-yl)[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester 3,3-dimethyl-2-oxobutyl ester 
• 1093214-94-8 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(morpholine-4-carbonyl)piperidine-4-carboxylic acid benzyl ester 
• 1093213-63-8 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}piperidine-4,4-dicarboxylic acid dibenzyl ester 
• 1093213-64-9 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(pyridin-2-ylcarbamoyl)piperidine-4-carboxylic acid benzyl ester 
• 1093213-16-1 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(piperidine-1-ylcarbamoyl)piperidine-4-carboxylic acid 
• 1093212-64-6 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid (2,2-dimethylpropanoyloxymethyl) ester 
• 1093212-86-2 1-{4-[5-(2-fluorobiphenyl-4-yl)[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid (3,3-dimethyl-2-oxobutyl) ester 
• 1093213-41-2 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(morpholine-4-carbonyl)piperidine-4-carboxylic acid 
• 1093214-95-9 4-chlorocarbonyl-1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4-carboxylic acid benzyl ester 

Relevant articles and documents

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.

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.