Tetrazole

Tetrazole Basic information
Description References
Product Name:Tetrazole
Synonyms:TETRAZOLE;1H-TETRAZOLE;1H-1,2,3,4-TETRAZOLE;1H-1,2,3,4-TETRAAZOLE;2H-TETRAZOLE;Tetrazole, 3 to 4 wt.% solution in acetonitrile, AcroSeal;Tetrazole 1H-Tetrazole;1H-Tetrazole [Coupling Agent]
CAS:288-94-8
MF:CH2N4
MW:70.05
EINECS:206-023-4
Product Categories:Chemistry;Tetrazoles;Other Reagents;Peptide Synthesis;Solvents and Mixtures for Peptide Synthesis;Specialty Synthesis;Biotech SolventsSolvents;Solvent Bottles;Solvents;Sure/Seal? Bottles;1
Mol File:288-94-8.mol
Tetrazole Structure
Tetrazole Chemical Properties
Melting point 156-158°C
Boiling point 220℃
density 0.798 g/mL at 20 °C
refractive index n20/D 1.348
RTECS UW7370000
Fp 5 °C
storage temp. Room temperature.
solubility DMSO, Methanol
form Liquid
pka4.9(at 25℃)
color Cream to orange
Water Solubility Soluble
Decomposition 220°C
BRN 105799
Stability:Stable at RT
InChIKeyKJUGUADJHNHALS-UHFFFAOYSA-N
CAS DataBase Reference288-94-8(CAS DataBase Reference)
NIST Chemistry Reference1H-Tetrazole(288-94-8)
EPA Substance Registry System1H-Tetrazole (288-94-8)
Safety Information
Hazard Codes F,Xn,E
Risk Statements 11-20/21/22-36-5-4
Safety Statements 16-26-36-36/37-35-15
RIDADR UN 1993 3/PG 2
WGK Germany 3
3-4.15-10
HazardClass 4.1
PackingGroup III
HS Code 29339900
MSDS Information
ProviderLanguage
1H-Tetrazole English
SigmaAldrich English
Tetrazole Usage And Synthesis
DescriptionTetrazole 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.
Referenceshttps://en.wikipedia.org/wiki/Tetrazole
https://pubchem.ncbi.nlm.nih.gov/compound/1H-Tetrazole#section=Information-Sources
Chemical Propertieswhite crystals or crystalline powder
UsesTetrazole 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.
Application1H-Tetrazole is used as a bioisostere for the carboxylate group. It is also used as coupling reagent for preparation of polynucleotides.
PreparationThe first tetrazole synthesis was reported in 1885.
Tetrazole Synthesis: Nano-TiCl4.SiO2 (0.1 g) was added to a mixture of benzonitrile (1 mmol), sodium azide (2 mmol) in DMF (5 mL) at reflux for 2 h. After completion of reaction (as monitored by TLC), the mixture was allowed to cool to room temperature, the catalyst was removed by filtration. Then by adding ice water and 4N HCl (5 mL) to the residue, a white solid was obtained. This was then washed with cold chloroform. This simple procedure yielded pure tetrazole with good yields.
DefinitionChEBI: 1H-tetrazole is a tetrazole tautomer where the proton is located on the 1st position. It is a tetrazole and a one-carbon compound. It is a tautomer of a 2H-tetrazole and a 5H-tetrazole.
General DescriptionTetrazole is an odorless white to light-yellow crystalline powder. Mp:1 55-157°C. When heated to decomposition Tetrazole emits toxic oxides of nitrogen fumes. Can explode if exposed to shock or heat from friction or fire. The primary hazard is from blast effect where the entire load can explode instantaneously and not from flying projectiles and fragments.
Health HazardFire may produce irritating, corrosive and/or toxic gases.
Fire HazardMAY EXPLODE AND THROW FRAGMENTS 1600 meters (1 MILE) OR MORE IF FIRE REACHES CARGO.
Purification MethodsCrystallise the tetrazole from EtOH and sublime it under high vacuum at ca 120o (care should be taken due to possible EXPLOSION). [Beilstein 26 H 346, 26 I 108, 26 II 196, 26 III/IV 1652.]
5-(1-PIPERIDINO)TETRAZOLE,5-(1-PIPERIDINO)TETRAZOLE,5-(1-PIPERIDINO)TETRAZOLE 5-[2-(4-CHLORO-3,5-DIMETHYL-PYRAZOL-1-YL)-ETHYL]-2H-TETRAZOLE,5-[2-(4-CHLORO-3,5-DIMETHYL-PYRAZOL-1-YL)-ETHYL]-2H-TETRAZOLE 1-[2-(Dimethylamino)ethyl]-1H-tetrazole-5-thiol Tetrazole 1H-Tetrazole-1-acetic acid 5-(1,3-BENZODIOXOL-5-YL)-2H-TETRAZOLE,5-(1,3-BENZODIOXOL-5-YL)-2H-TETRAZOLE 5-([2-(4-CHLOROPHENOXY)ETHYL]THIO)-1-PHENYL-1H-TETRAZOLE,5-([2-(4-CHLOROPHENOXY)ETHYL]THIO)-1-PHENYL-1H-TETRAZOLE 1-(2-FURYLMETHYL)-1H-TETRAZOLE-5-THIOL 5-(1-PYRROLIDINO)TETRAZOLE,5-(1-PYRROLIDINO)TETRAZOLE,5-(1-PYRROLIDINO)TETRAZOLE 5-([2-(2-METHYLPHENOXY)ETHYL]THIO)-1-PHENYL-1H-TETRAZOLE 5-(1H-PYRAZOL-1-YL)-1H-TETRAZOLE,5-(1H-PYRAZOL-1-YL)-1H-TETRAZOLE,5-(1H-PYRAZOL-1-YL)-1H-TETRAZOLE 5-(2-BROMO-PHENYL)-2H-TETRAZOLE,5-(2-BROMO-PHENYL)-2H-TETRAZOLE 5-([2-(3,4-DIMETHYLPHENOXY)ETHYL]THIO)-1-(4-METHYLPHENYL)-1H-TETRAZOLE 5-Mercapto-1-methyltetrazole Nitrotetrazolium blue chloride 5-(Methylthio)-1H-tetrazole 2,3,5-Triphenyltetrazolium chloride 5-Phenyltetrazole

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