132372-75-9

Basic information

• Product Name: 1H-TETRAZOLE, 5-[(4-METHOXYPHENYL)METHYL]-
• Synonyms: 1H-TETRAZOLE, 5-[(4-METHOXYPHENYL)METHYL]-;5-(4-methoxybenzyl)-2H-tetraazole
• CAS NO: 132372-75-9
• Molecular Formula: C₉H₁₀N₄O
• Molecular Weight: 190.2019
• Mol File: 132372-75-9.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-TETRAZOLE, 5-[(4-METHOXYPHENYL)METHYL]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-TETRAZOLE, 5-[(4-METHOXYPHENYL)METHYL]-(132372-75-9)
• EPA Substance Registry System: 1H-TETRAZOLE, 5-[(4-METHOXYPHENYL)METHYL]-(132372-75-9)

Safety Data

• Hazardous Substances Data: 132372-75-9(Hazardous Substances Data)

Usage

Chemical Family

Tetrazoles

Biological Activities

Diverse, including potential applications in the treatment of cardiovascular diseases, cancer, and inflammation.

Structure

A 4-methoxyphenylmethyl group attached to the 5-position of the tetrazole ring.

Value in Pharmaceutical Science

A valuable building block for the development of novel drugs and therapeutic agents due to its unique structure and properties.

Current Status

Commonly used in pharmaceutical and medical research, with further research and exploration of its biological activities potentially leading to the discovery of new medical treatments and advancements in the field.

Upstream product

• 14191-95-8 4-cyanomethylphenol 
• 104-47-2 p-methoxybenzylnitrile 

Downstream Products

• 132372-84-0 [5-(4-Methoxy-benzyl)-tetrazol-1-yl]-acetic acid 
• 132372-93-1 [5-(4-Methoxy-benzyl)-tetrazol-2-yl]-acetic acid 
• 1283134-70-2 2,3,4,6-tetra-O-acetyl-1-{5-[(4-methoxyphenyl)methyl]-1H-tetrazol-1-yl}-1-deoxy-β-D-galactopyranose 
• 1283134-65-5 2,3,4,6-tetra-O-acetyl-1-{5-[(4-methoxyphenyl)methyl]-2H-tetrazol-2-yl}-1-deoxy-β-D-galactopyranose 
• 1283134-69-9 2,3,4,6-tetra-O-acetyl-1-{5-[(4-methoxyphenyl)methyl]-1H-tetrazol-1-yl}-1-deoxy-β-D-glucopyranose 
• 1208092-59-4 2,3,4,6-tetra-O-acetyl-1-{5-[(4-methoxyphenyl)methyl]-2H-tetrazol-2-yl}-1-deoxy-β-D-glucopyranose 

Relevant articles and documents

OSU-6: A highly efficient, metal-free, heterogeneous catalyst for the click synthesis of 5-benzyl and 5-aryl-1H-tetrazoles

OSU-6, an MCM-41 type hexagonal mesoporous silica with mild Br?nsted acid properties, has been used as an efficient, metal-free, heterogeneous catalyst for the click synthesis of 5-benzyl and 5-aryl-1H-tetrazoles from nitriles in DMF at 90 °C. This catalyst offers advantages including ease of operation, milder conditions, high yields, and reusability. Studies are presented that demonstrate the robust nature of the catalyst under the optimized reaction conditions. OSU-6 promotes the 1,3-dipolar addition of azides to nitriles without significant degradation or clogging of the nanoporous structure. The catalyst can be reused up to five times without a significant reduction in yield, and it does not require treatment with acid between reactions.

Synthesis of 5-Substituted Tetrazoles from Nitriles Catalyzed by Sulfamic Acid

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β-Cyclodextrin-mediated highly efficient [2+3] cycloaddition reactions for the synthesis of 5-substituted 1H-tetrazoles

A β-cyclodextrin-promoted [2+3] cycloaddition reaction between nitriles and sodium azide in the presence of ammonium chloride in DMF at 120 °C is reported, affording various 5-substituted 1H-tetrazoles in good to excellent yields in short reaction times. The presence of β-CD renders the formation of a precipitate-like gel in the reaction media when heated. No precipitation occurs in the absence of NaN3 and NH4Cl. The precipitation responses with other salts such as LiCl and NiCl2 were weaker than with NH4Cl. In the present paper the application of supramolecular aggregates is reported for the [2+3] cycloaddition reaction. β-Cyclodextrin can be recovered and reused without any significant loss of activity.

Ammonium acetate mediated synthesis of 5-substituted 1H-tetrazoles

Synthesis of 5-substituted 1H-tetrazoles was achieved by [3+2] cycloaddition of nitriles and sodium azide in the presence of ammonium acetate. The reaction proceeds in situ formation of ammonium azide. Present protocol has advantage of good to excellent yields, short reaction times and simple isolation of products than reported methods. Iranian Chemical Society 2012.

Lithiation Substitution of Unprotected Benzyltetrazoles

1H-Tetrazoles occupy an important role in modern medicinal chemistry, but few methods for their modification exist. Many extant protocols require the use of a difficult to remove N-alkyl-protecting group, precluding the products from use as carboxylate bioisosteres, the major role of tetrazoles in pharmaceuticals. We herein report a convenient, protecting-group-free lithiation-substitution protocol for benzylic tetrazoles. Metalation with n-BuLi at 0 °C followed by electrophilic trapping gave a range of α-functionalized benzyltetrazoles in up to 91% yield.