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

Flash point:

5 °C

storage temp. 

Room temperature.

solubility 

DMSO, Methanol

form 

Liquid

pka

4.9(at 25℃)

color 

Cream to orange

Water Solubility 

Soluble

Decomposition 

220°C

BRN 

105799

Stability:

Stable at RT

InChIKey

KJUGUADJHNHALS-UHFFFAOYSA-N

CAS DataBase Reference

288-94-8(CAS DataBase Reference)

NIST Chemistry Reference

1H-Tetrazole(288-94-8)

EPA Substance Registry System

1H-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

F 

3-4.15-10

HazardClass 

4.1

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:1H-Tetrazole
• Language:English Provider:SigmaAldrich

Tetrazole Usage And Synthesis

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.

References

https://en.wikipedia.org/wiki/Tetrazole
https://pubchem.ncbi.nlm.nih.gov/compound/1H-Tetrazole#section=Information-Sources

Chemical Properties

white crystals or crystalline powder

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.

Application

1H-Tetrazole is used as a bioisostere for the carboxylate group. It is also used as coupling reagent for preparation of polynucleotides.

Preparation

The 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.

Definition

ChEBI: 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 Description

Tetrazole 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 Hazard

Fire may produce irritating, corrosive and/or toxic gases.

Fire Hazard

MAY EXPLODE AND THROW FRAGMENTS 1600 meters (1 MILE) OR MORE IF FIRE REACHES CARGO.

Purification Methods

Crystallise 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.]

Tetrazole(288-94-8)Related Product Information

• 5-Mercapto-1-methyltetrazole
• Nitrotetrazolium blue chloride
• 1H-Tetrazole-1-acetic acid
• 2,3,5-Triphenyltetrazolium chloride
• 5-Phenyltetrazole
• 5-Mercapto-1H-tetrazole-1-methanesulfonic acid disodium salt
• 5-(2,3-DICHLOROPHENYL)-1H-TETRAZOLE,5-(2,3-DICHLOROPHENYL)TETRAZOLE,5-(2,3-DICHLOROPHENYL)-1H-TETRAZOLE,5-(2,3-DICHLOROPHENYL)TETRAZOLE
• 1H-TETRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER SODIUM SALT
• 5-(Methylthio)-1H-tetrazole
• 1-[2-(Dimethylamino)ethyl]-1H-tetrazole-5-thiol
• 5-(2,4-DICHLOROPHENYL)-1H-TETRAZOLE,5-(2,4-DICHLOROPHENYL)-1H-TETRAZOLE,5-(2,4-DICHLOROPHENYL)-1H-TETRAZOLE
• 5-(2,6-DICHLOROPHENYL)-1H-TETRAZOLE,5-(2,6-DICHLOROPHENYL)-1H-TETRAZOLE
• 1-(M-SULFOPHENYL)-5-MERCAPTO-1H-TETRAZOLE SODIUM SALT
• 1H-TETRAZOLE, 1-PHENYL-5-THIOL
• 5-(2,5-DICHLOROPHENYL)-1H-TETRAZOLE,5-(2,5-DICHLOROPHENYL)-1H-TETRAZOLE
• 5-(2,6-DIFLUOROPHENYL)TETRAZOLE,5-(2,6-DIFLUOROPHENYL)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
• 5-(2-BROMO-BENZYL)-2H-TETRAZOLE,5-(2-BROMO-BENZYL)-2H-TETRAZOLE