50907-19-2

Basic information

• Product Name: 5-(2-FLUOROPHENYL)-1H-1,2,3,4-TETRAAZOLE
• Synonyms: 5-(2-FLUOROPHENYL)-1H-1,2,3,4-TETRAAZOLE;5-(2-Fluorophenyl)-2H-tetrazole
• CAS NO: 50907-19-2
• Molecular Formula: C₇H₅FN₄
• Molecular Weight: 164.1398032
• Mol File: 50907-19-2.mol

Chemical Properties

• Melting Point: 157-159°C
• Boiling Point: 331.8°C at 760 mmHg
• Flash Point: 154.5°C
• Appearance: /
• Density: 1.403g/cm³
• Vapor Pressure: 0.000152mmHg at 25°C
• Refractive Index: 1.591
• PKA: 3.70±0.10(Predicted)
• BRN: 1105868
• CAS DataBase Reference: 5-(2-FLUOROPHENYL)-1H-1,2,3,4-TETRAAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-FLUOROPHENYL)-1H-1,2,3,4-TETRAAZOLE(50907-19-2)
• EPA Substance Registry System: 5-(2-FLUOROPHENYL)-1H-1,2,3,4-TETRAAZOLE(50907-19-2)

Safety Data

• Hazardous Substances Data: 50907-19-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-(2-FLUOROPHENYL)-1H-1,2,3,4-TETRAAZOLE is used as a synthetic intermediate for the preparation of novel tetrazole derivatives. These derivatives act as positive allosteric modulators of metabotropic glutamate receptors (mGluR5), which are involved in the treatment and prevention of central nervous system (CNS) diseases and other conditions modulated by mGluR5 receptors.
5-(2-FLUOROPHENYL)-1H-1,2,3,4-TETRAAZOLE's role in the development of new therapeutic agents for CNS diseases highlights its importance in the pharmaceutical industry, as it can potentially contribute to the creation of more effective treatments for a range of neurological and psychiatric disorders.

InChI:InChI=1/C7H5FN4/c8-6-4-2-1-3-5(6)7-9-11-12-10-7/h1-4H,(H,9,10,11,12)

Upstream product

• 394-47-8 2-fluorobenzonitrile 
• 24652-66-2 2-fluorobenzaldehyde oxime 

Downstream Products

• 497102-17-7 C₁₁H₁₁FN₄O₂ 
• 120568-11-8 2-(tetrazol-5-yl)-4'-methyl-1,1'-biphenyl 

Relevant articles and documents

5-Aryltetrazoles from Direct C-H Arylation with Aryl Bromides

A mild, direct C-H arylation of 1-substituted tetrazoles to 5-aryltetrazoles is developed using a Pd/Cu cocatalytic system with readily available aryl bromides. The methodology avoids late-stage usage of azides and tolerates a wide range of functionalities.

Discovery, synthesis and characterization of a series of (1-alkyl-3-methyl-1H-pyrazol-5-yl)-2-(5-aryl-2H-tetrazol-2-yl)acetamides as novel GIRK1/2 potassium channel activators

The present study describes the discovery and characterization of a series of 5-aryl-2H-tetrazol-3-ylacetamides as G protein-gated inwardly-rectifying potassium (GIRK) channels activators. Working from an initial hit discovered during a high-throughput screening campaign, we identified a tetrazole scaffold that shifts away from the previously reported urea-based scaffolds while remaining effective GIRK1/2 channel activators. In addition, we evaluated the compounds in Tier 1 DMPK assays and have identified a (3-methyl-1H-pyrazol-1-yl)tetrahydrothiophene-1,1-dioxide head group that imparts interesting and unexpected microsomal stability compared to previously-reported pyrazole head groups.

Triple reuptake inhibitors: Design, synthesis and structure–activity relationship of benzylpiperidine–tetrazoles

Monoamine transporters are important targets in the treatment of various central nervous disorders. Several limitations of traditional reuptake inhibitors, like delayed onset of action, insomnia, and sexual dysfunction, have compelled the search for safer, more effective compounds. In this study, we have sought to identify novel monoamine reuptake inhibitors. Based upon the docking study of compounds that we had reported previously, aromatic rings (A1) were modified to generate a novel series of benzylpiperidine–tetrazoles. Thirty-one compounds were synthesized and evaluated for their triple reuptake inhibition of serotonin, norepinephrine and dopamine. Triple reuptake inhibitor, compound 2q, in particular, showed potent serotonin reuptake inhibition, validating our design approach.

Indium(III) Chloride Catalyzed Synthesis of 5-Substituted 1 H -Tetrazoles from Oximes and Sodium Azide

A simple and efficient protocol has been developed for the synthesis of 5-substituted 1H-tetrazole derivatives in good to excellent yields from various oximes and sodium azide by using indium(III) chloride as a Lewis acid catalyst. The present method has

Discovery and optimization of a novel series of N-arylamide oxadiazoles as potent, highly selective and orally bioavailable cannabinoid receptor 2 (CB 2) agonists

The CB2 receptor is an attractive therapeutic target for analgesic and anti-inflammatory agents. Herein we describe the discovery of a novel class of oxadiazole derivatives from which potent and selective CB 2 agonist leads were developed. Initial hit 7 was identified from a cannabinoid target-biased library generated by virtual screening of sample collections using a pharmacophore model in combination with a series of physicochemical filters. 7 was demonstrated to be a selective CB2 agonist (CB2 EC50 = 93 nM, Emax = 98%, CB 1 EC50 > 10 μM). However, this compound exhibited poor solubility and relatively high clearance in rat, resulting in low oral bioavailability. In this paper, we report detailed SAR studies on 7 en route toward improving potency, physicochemical properties, and solubility. This effort resulted in identification of 63 that is a potent and selective agonist at CB2 (EC50 = 2 nM, Emax = 110%) with excellent pharmacokinetic properties.

1,3-Dipolar cycloaddition: Click chemistry for the synthesis of 5-substituted tetrazoles from organoaluminum azides and nitriles

Cheap and safe: Conventional methods to prepare tetrazoles employ dangerous, toxic reagents. A new route to these heterocycles (see scheme) uses inexpensive and nontoxic dialkyl aluminum azides. The cycloaddition occurs under mild conditions and tolerates a variety of functional groups. The low cost and ecocompatibility make this process attractive for large-scale preparation. (Chemical Equation Presented).

A practical synthesis of 5-(4′-methylbiphenyl-2-yl)-1H-tetrazole

Practical synthesis of 5-(4′-methylbiphenyl-2-yl)-1H-tetrazole, key intermediate in several angiotensin II receptor antagonists from 2-fluorobenzonitrile in excellent yields and very high purity is described.

PROCESS FOR THE PREPARATION OF TETRAZOLE DERIVATIVES FROM ORGANO BORON AND ORGANO ALUMINIUM AZIDES

The present invention relates to a method for preparing substituted tetrazoles, compounds obtained according to this method, new reactants and new tetrazole derivatives.

5-Aryltetrazole Compounds, compositions thereof, and uses therefor

The present invention relates to 5-Aryltetrazole compounds, compositions comprising a 5-Aryltetrazole compound, and methods for treating an inflammation disease, a reperfusion disease, hyperuricemia, gout, or tumor-lysis syndrome in an animal in need ther