90329-50-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Ethyl-1-methyl-1H-tetrazole is used as a pharmaceutical intermediate for the synthesis of various drugs, including candesartan, an angiotensin II receptor antagonist used for the treatment of hypertension. Its role in drug synthesis is crucial for the development of medications that help manage blood pressure and cardiovascular health.
Used in Explosives Industry:
In the explosives industry, 5-ethyl-1-methyl-1H-tetrazole serves as a stabilizer in the synthesis of explosives. Its stabilizing properties contribute to the safety and reliability of explosive materials, ensuring controlled reactions and minimizing the risk of accidental detonation.
Used in Corrosion Prevention:
5-Ethyl-1-methyl-1H-tetrazole is also used as an inhibitor in corrosion prevention. Its application in this field helps protect metal surfaces from corrosion, extending the lifespan of structures and equipment, and reducing maintenance costs.

InChI:InChI=1/C4H8N4/c1-3-4-5-6-7-8(4)2/h3H2,1-2H3

Upstream product

• 78-93-3 butanone 
• 107574-63-0 C₄H₈N⁽¹⁺⁾*FO₃S^(1-) 
• 5144-11-6 1,5-dimethyl-1H-tetrazole 
• 74-88-4 methyl iodide 
• 16687-59-5 5-ethyl-1H-1,2,3,4-tetrazole 

Downstream Products

• 142868-08-4 5-Ethyl-4-methyl-1-(2-oxo-2-phenyl-ethyl)-4H-tetrazol-1-ium; bromide 
• 118875-67-5 1,1-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)propanol 

Relevant academic research and scientific papers

Antihypercholesterolemic tetrazole compounds

Compounds of the formula STR1 wherein R1 and R4 each are independently hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, or trifluoromethyl; R2, R3, R5 and R6 each are independently hydrogen, halogen C1-4 alkyl or C1-4 alkoxy; tet is STR2 n is an integer of from 0 to 2, inclusive; A is STR3 R7 is hydrogen, C1-4 alkyl, C1-4 alkoxy(lower) alkyl or (2-methoxyethoxy)methyl; X is --OH or =O; and R8 is hydrogen, a hydrolyzable ester group or a cation to form a non-toxic pharmaceutically acceptable salt, are novel antihypercholesterolemic agents which inhibit cholesterol biosynthesis. Intermediates and processes for their preparation are disclosed.

Intermediates for the preparation of antihypercholesterolemic tetrazole compounds

This invention provides novel tetrazole intermediates of the formula STR1 wherein R1 and R4 each are independently hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy or trifluoromethyl; R2,R3,Rsup

Synthesis, biological profile, and quantitative structure - Activity relationship of a series of novel 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors

A series of 9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(alkyltetrazol-5-yl)-6,8-nonad ienoic acid derivatives 1 were synthesized and found to inhibit competitively the enzyme 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase. The analogues having 1N-methyltetrazol-5-yl attached to the C8-position (3a, 4a, R1 = R2 = F) are the most active in suppressing cholesterol biosynthesis in both in vitro and in vivo models: the IC50 for the chiral form of 3a is 19 nM, K(i) = 4.3 x 10-9 M when K(m) for HMG-CoA is 28 x 10-6 M; the ED50 (oral) value corresponding to the lactone derivative (4a, BMY 22089) is approximately 0.1 mg/kg. Further, BMY 21950 is nearly 2 orders of magnitude more active in parenchymal hepatocytes, from which most of the serum cholesterol originates, than in other cell preparations (such as spleen, testes, ileum, adrenal, and ocular lens epithelial cells; Table III). This apparent tissue specificity may be highly beneficial since the blocking of cholesterol biosynthesis in other vital organs could eventually lead to undesirable side effects. In addition to the chemical synthesis and biological evaluation, a theoretical study aimed at relating the HMG-CoA reductase inhibitory potency to the three-dimensional structure of the inhibitors was undertaken. With a combination of molecular mapping and 3D-QSAR techniques, it was possible to determine a logical candidate for the conformation of the bound inhibitor and to quantitatively relate inhibitory potency to the shape and size of both the binding site and the C8-substituent.

Intermediates for antihypercholesterolemic tetrazole compounds

This invention provides novel intermediates of the formula STR1 in substantially the cis or cis-(4R,6S) form wherein R9 and R10 each are C1-4 alkyl or R9 and R10, taken together with the carbon atom to which they are attached, is cyclopentyl, cyclohexyl or cycloheptyl; and R12 is hydrogen, C1-4 alkyl or a metal cation and processes thereof which are useful for the preparation of antihypercholesterolemic agents.

Photochemical Formation of Heteromethylenecyclopropanes, 16. - 1,4,5-Substituted Tetrazolium Salts Through Methylation of 1,5-Substituted Tetrazoles and Cycloaddition of Alkyl Azides to Nitrilium Ions

Efficient syntheses of isomerically pure 1,4,5-substituted tetrazolium salts are reported.Methylation of 1,5-substituted tetrazoles 5 affords mixtures of 1,4,5- (1) and 1,3,5-substituted tetrazolium salts 6.The ratio 1:6 depends only little on the reaction conditions as well as on the methylating agents.The isomerically pure tetrazolium salts 1a-e, g, j, k and 6j, k are isolated by fractionating crystallizations. tert-Butylation of 5a, c using tert-butyl alcohol/tetrafluoroboric acid produces only the 3-tert-butyltetrazolium tetrafluoroborates 9a, c.The N-methylnitrili um tetrafluoroborates, fluorosulfonates or trifluoromethanesulfonates 7a-c and e cycloadd the alkyl azides 8a-d regioselectively to the tetrazolium salts 1a-c, e, f, h, i.Both rate and yield of the cycloaddition decrease with increasing size of the substituents.The N-tert-butylnitrilium tetrachloroferrate 7h (X=FeCl4) reacts with methyl azide (8a) yielding the hydrogen tetrachloroferrate 4a*HFeCl4 of the imidoyl chloride 4a.

ADDITION REACTION OF TRIMETHYLSILYL AZIDE TOWARDS KETONES AND FACILE FORMATION OF TETRAZOLE DERIVATIVES

In the presence of Lewis acid such as SnCl2, the reactions of trimethylsilyl azide with ketones readily gave 1:1- or 1:2-adduct, which reacted with Lewis acid to afford tetrazole.