120568-11-8

Basic information

• Product Name: 5-[2-(4'-METHYLBIPHENYL)]TETRAZOLE
• Synonyms: 2-(Tetrazol-5-yl)-4'-Methyl-1,1'-biphenyl;2H-Tetrazole,5-(4'-Methyl[1,1'-biphenyl]-;Losartan EP IMpurity E;524-10;Valsartan Impurity 4;5-[2-(4'-METHYLBIPHENYL)]TETRAZOLE;5-(4''-METHYLBIPHENYL-2-YL)-1H-TETRAZOLE;5-(4'-Methyl-2-biphenyl)tetrazole
• CAS NO: 120568-11-8
• Molecular Formula: C₁₄H₁₂N₄
• Molecular Weight: 236.277
• EINECS: 1592732-453-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Heterocycles;Impurities
• Mol File: 120568-11-8.mol

Chemical Properties

• Melting Point: 150 °C
• Boiling Point: 458.396 °C at 760 mmHg
• Flash Point: 214.529 °C
• Appearance: /
• Density: 1.216 g/cm³
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.17±0.10(Predicted)
• CAS DataBase Reference: 5-[2-(4'-METHYLBIPHENYL)]TETRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[2-(4'-METHYLBIPHENYL)]TETRAZOLE(120568-11-8)
• EPA Substance Registry System: 5-[2-(4'-METHYLBIPHENYL)]TETRAZOLE(120568-11-8)

Safety Data

• Hazardous Substances Data: 120568-11-8(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Pale Beige Solid

Uses

Valsartan (V095750) impurity.

Upstream product

• 114772-53-1 2-Cyano-4'-methylbiphenyl 
• 120568-17-4 5-<4'-Methyl-1,1'-biphenyl-2-yl>-1H-tetrazole-1-propanenitrile 
• 106-38-7 para-bromotoluene 
• 2042-37-7 o-cyanobromobenzene 
• 7148-03-0 o-tolylbenzoic acid 
• 114772-35-9 4'-methylbiphenyl-2-carboxylic acid chloride 
• 120568-15-2 N-(2-cyanoethyl)-4'-methyl[1,1']biphenyl-2-carboxamide 
• 132979-85-2 N-(2-Cyano-ethyl)-4'-methyl-biphenyl-2-carboximidoyl chloride 
• 120568-16-3 N-(2-Cyanoethyl)-4'-methyl-1,1'-biphenyl-2-carboximidic Acid Hydrazide 
• 1080555-70-9 C₃₃H₃₇N₅O₃ 
• 50907-19-2 5-(2-fluorophenyl)-1H-tetrazole 
• 394-47-8 2-fluorobenzonitrile 
• 71-36-3 butan-1-ol 
• 233585-27-8 C₁₄H₁₃NO 

Downstream Products

• 133909-97-4 N-(trityl)-5-[4?-(methyl)biphenyl-2-yl]-2H-tetrazole 
• 133051-88-4 N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole 
• 179089-06-6 C₂₁H₁₈N₄ 
• 1084949-70-1 5-butyl-2-hydroxymethyl-1-[[2'-[[N-(2-chlorotrityl)]tetrazol-5-yl]biphenyl-4-yl]methyl]imidazole 
• 1295434-61-5 Br^(1-)*C₄₇H₄₃N₆⁽¹⁺⁾ 
• 1084949-39-2 5-butyl-2-hydroxymethyl-1-[[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole trifluoroacetic acid 
• 1084950-09-3 N-(benzyl)-5-[4'-(bromomethyl)-biphenyl-2-yl]tetrazole 
• 1295434-59-1 Br^(1-)*C₅₉H₅₁N₆⁽¹⁺⁾ 
• 1084949-34-7 5-butyl-1-[[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole trifluoroacetic acid 
• 1084949-66-5 5-butyl-1-[[2'-[[N-(2-chlorotrityl)]tetrazol-5-yl]biphenyl-4-yl]methyl]imidazole 
• 155092-07-2 1-<<2'-<(N-triphenylmethyl)tetrazol-5-yl>biphenyl-4-yl>methyl>-4-butylimidazole-2-carboxaldehyde 
• 1400934-09-9 C₄₁H₃₆N₆O₂ 
• 1400933-86-9 5-butyl-1-[[(2'-(2-trityl)-tetrazol-5-yl)biphenyl-4-yl]methyl]-3-[(2-(trimethylsilyl)ethoxy)methyl]-1H-imidazolium bromide 
• 1400933-88-1 5-butyl-2-hydroxymethyl-1-[[(2'-(2-trityl)-2H-tetrazol-5-yl)biphenyl-4-yl]methyl]-3-[(2-(trimethylsilyl)ethoxy)methyl]-1H-imidazolium bromide 

Relevant articles and documents

Regio- and Enantioselective Synthesis of Azole Hemiaminal Esters by Lewis Base Catalyzed Dynamic Kinetic Resolution

We report a modular three-component dynamic kinetic resolution (DKR) that affords enantiomerically enriched hemiaminal esters derived from azoles and aldehydes. The novel and scalable reaction can be used to synthesize valuable substituted azoles in a regioselective manner by capping (e.g., acylation) of the equilibrating azole-aldehyde adduct. With the use of a prolinol-derived DMAP catalyst as the chiral Lewis base, the products can be obtained in high chemical yield and with high enantiomeric excess. The DKR was performed on a multikilogram scale to produce a tetrazole prodrug fragment for a leading clinical candidate that posed formidable synthesis challenges.

Solid phase synthesis of biphenyltetrazole derivatives

A dihydropyran carboxylic acid type linker is suitable for the solid phase Suzuki type aryl-aryl coupling reaction for the preparation of various biphenyltetrazole derivatives.

Safe and fast tetrazole formation in ionic liquids

The [2+3] cycloaddition of nitriles and azides is reliable for intramolecular reactions, but the hazards with volatile azides in intermolecular reactions are tremendous. Zinc catalysis in aqueous solution is a magnificent improvement, but requires the removal of the zinc salts from the acidic product. Herein, we report safe solvents featuring low vapor pressure and good solubility of NaN3. Ionic liquids based on alkylated imidazoles combined with microwave heating turned out to be a solution for the given tasks.

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.

Synthesis and selective cytotoxicity of novel biphenyl-based tetrazole derivatives

Cancer today represents a significant public health problem worldwide, and the challenge is to produce cost-effective drugs. Recently, biphenyl compounds as well as tetrazole derivatives is known for their potential nonselective anticancer activities. In search of novel selective anticancer agents, a series of newly hybrid molecules was designed and synthesized by combining the structural features of biphenyl and tetrazole moieties. The structures of newly synthesized compounds were characterized using spectroscopic techniques (FT-IR, 1H NMR, 13C NMR, and HMBC). Cytotoxic evaluations of these novels compound on human cancer cell lines showed a significant anticancer activity against more than one tested cell lines. Compounds 5n, 5j, and 5o proved to exhibit the strongest and selective cytotoxic effect on HepG2 and MCF-7 lines. Taken together, this study has led to the development of promising leads for cancer therapy.

Synthesis of 5-substituted lH-tetrazoles from nitriles and hydrazoic acid by using a safe and scalable high-temperature microreactor approach

Harnessing hydrazoic acid in a microreactor! Tetrazoles have been synthesized in a very efficient manner by using a high-temperature/high-pressure process intensification regime. Despite the toxic and explosive nature of hydrazoic acid, the synthesis was conducted safely in continuous flow format with residence times as short as 2.5 minutes at 260□°C (see picture).

Urea mediated 5-substituted-1H-tetrazole via [3?+?2] cycloaddition of nitriles and sodium azide

A simple, new and convenient metal free procedure for the synthesis of 5-substituted 1H-tetrazoles using various nitriles and sodium azide in the presence of urea and acetic acid with good to high yields is developed. The reaction plausibly proceeds through in situ formation of urea azide active complex without toxic and/or expensive metal catalysts.

Synthesis and characterization of 4′-bromomethyl-2-(N-trityl-1H- tetrazol-5-yl) biphenyl

Biphenyl tetrazole ring is an important component of the Sartan family of novel drugs. 4′-Bromomethyl-2-(N-trityl-1H-tetrazol-5-yl)biphenyl was synthesized in this article from 4′-methyl-2-cyano-biphenyl through three steps. 4′-Methyl-2-cyano-biphenyl was reacted with azide ions with the help of ammonium chloride as catalyst in an autoclave with high conversion to afford the tetrazole compounds in 70.6% yield. After being protected by the trityl group with 92.6% yield, 4′-methyl-2-(N-trityl-1H-tetrazol-5-yl) biphenyl was brominated with N-bromosuccinimide (NBS) in cyclohexane with 2,2′-azo-isobutyronitrile (AIBN) acting as an initiator to provide the title compound in 83.8% yield. Copyright Taylor & Francis Group, LLC.

Zn/MeOH-Mediated Practical and Easy Detritylation of Protected 1-Trityltetrazoles

A practical and low-cost method for the detritylation of 1-titryltetrazoles using zinc and methanol is described. This procedure is versatile and efficient in the deprotection of several protected tetrazoles bearing aliphatic, aromatic, and heteroaromatic substituents, as well as some functional groups, without decomposition of the tetrazole ring.

Detritylation of protected tetrazoles by naphthalene-catalyzed lithiation

Treatment of N-tritylated tetrazoles bearing aliphatic, aromatic, or heteroaromatic substituents (including functionalized ones) with lithium powder and a catalytic amount of naphthalene led to reductive removal of the trityl group to give excellent yields of the corresponding free tetrazoles without decomposition of the tetrazole ring. The detritylation process was successfully extended to several tetrazoles that are components of sartans, an interesting class of drugs. The chemoselectivity between trityl-tetrazole and trityl-amine bond-cleavage reactions was also studied. This method represents an efficient technique for deprotection of tritylated tetrazoles under non-acidic conditions. Georg Thieme Verlag Stuttgart, New York.