1H-Tetrazole

Base Information

• Chemical Name: 1H-Tetrazole
• CAS No.: 288-94-8
• Molecular Formula: CH2N4
• Molecular Weight: 70.0537
• Hs Code.: 2933.99
• European Community (EC) Number: 206-023-4
• NSC Number: 36712
• UN Number: 0504
• UNII: D34J7PAT68
• DSSTox Substance ID: DTXSID5075280
• Nikkaji Number: J390E,J2.572.129B
• Wikipedia: Tetrazole
• Wikidata: Q58826308,Q58826418
• Metabolomics Workbench ID: 54864
• ChEMBL ID: CHEMBL2148103
• Mol file: 288-94-8.mol

Synonyms:1H-tetrazole;1H-tetrazole, monohydrogen iodide;1H-tetrazole, silver salt;tetrazole

Chemical Property of 1H-Tetrazole

Chemical Property:

• Appearance/Colour: white crystals or crystalline powder
• Vapor Pressure: 394mmHg at 25°C
• Melting Point: 156-158 °C
• Refractive Index: n20/D 1.348
• Boiling Point: 220.233 °C at 760 mmHg
• PKA: 4.9(at 25℃)
• Flash Point: 114.573 °C
• PSA: 54.46000
• Density: 1.477 g/cm³
• LogP: -0.80030
• Storage Temp.: Room temperature.
• Solubility.: DMSO, Methanol
• Water Solubility.: Soluble
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 70.027946081
• Heavy Atom Count: 5
• Complexity: 26.8
• Transport DOT Label: Explosive 1.1D

Purity/Quality:

98%min ^*data from raw suppliers

1H-Tetrazole, 0.45M in acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn,E
• Statements: 11-20/21/22-36-5-4
• Safety Statements: 16-26-36-36/37-35-15

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Rings
• Canonical SMILES: C1=NNN=N1
• Description: Tetrazole is a class of synthetic organic heterocyclic compound containing a 5-member ring of four nitrogen atoms and one carbon atom. It appears as an odorless white to light-yellow crystalline powder. It has several pharmaceutical applications. Tetrazole compound can act as a bioisotere for the carboxylate group, angiotensin II receptor blockers such as losartan and candesartan as well as dimethyl thiazolyl diphenyl tetrazolium bromide (MTT), which can be used in MTT assay for quantifying the respiratory activity of liver cells. It can also be used in DNA assays. In addition, Tetrazole derivatives have also been used in explosives such as TNT or high performance solid rocket propellant formulations. Tetrazole can be synthesized through the reaction between anhydrous hydrazoic acid and hydrogen cyanide under pressure.
• Uses: Tetrazole is a catalyst for phosphoramidite synthesis. It is also used as an intermediate for the drug cilostazol. Cilostazol is an antiplatelet drug and a vasodilator. Tetrazole derivatives are used as antibiotics and optically active tetrazole-containing antifungal preparations of azole type was reported.

Technology Process of 1H-Tetrazole

There total 82 articles about 1H-Tetrazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.55%

orthoformic acid triethyl ester (122-51-0) → 1H-tetrazole (288-94-8)

Guidance literature:

With sodium azide; ammonium chloride; acetic acid; at 90 ℃; for 10h;

DOI:10.1002/zaac.201400486

Reference yield: 85.0%

ethyl cyanoformate (623-49-4) → 1H-tetrazole (288-94-8)

Guidance literature:

With sodium azide; triethylamine hydrochloride; In N,N-dimethyl-formamide; at 130 ℃; for 4h; Microwave irradiation; Inert atmosphere;

DOI:10.1055/s-0032-1318476

Reference yield:

benzamidine tetrazole salt → 1H-tetrazole (288-94-8) + benzamidin (618-39-3)

Guidance literature:

In methanol; acetonitrile; Equilibrium constant;

DOI:10.1021/ol053072+

upstream raw materials:

5-iodo-1H-tetrazole

sodium ethanolate

5-aminotetrazole

4-tetrazol-1-yl-phenylamine

Downstream raw materials:

1-methyl-1,2,3,4-tetrazole

N,N'-dibenzoylurea

N'-benzoylbenzohydrazide

3-(1H-tetrazol-1-yl)propanoic acid

Refernces

• 1、 Kabo, G. J.,Kozyro, A. A.,Krasulin, A. P.,Sevruk, V. M.,Ivashkevich, L. S.. "Thermodynamic properties and tautomerism of tetrazole". . p. 485 - 493. Retrieved 1993.
• 2、 Wang, Xiaojun,Liu, Jiping,Wang, Dong,Bi, Xiaolu,Zhao, Wei. "Synthesis and Characterization of Sodium 5-Chlorotetrazolate Dihydrate by Chlorination of 1H-Tetrazole". . p. 631 - 635. Retrieved 2015.
• 3、 Zeisel, Lukas,Szimhardt, Norbert,Wurzenberger, Maximilian H. H.,Klap?tke, Thomas M.,Stierstorfer, J?rg. "2-Methyl-substituted monotetrazoles in copper(ii) perchlorate complexes: manipulating coordination chemistry and derived energetic properties". supporting information. p. 609 - 616. Retrieved 2019/01/10.