3-(2H-TETRAZOL-5-YL)-PYRIDINE

3-(2H-TETRAZOL-5-YL)-PYRIDINE Property

Melting point:

240 °C

Boiling point:

379.4±44.0 °C(Predicted)

Density 

1.388±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

5.99±0.12(Predicted)

Appearance

White to off-white Solid

Water Solubility 

Soluble in water (slightly).

InChI

InChI=1S/C6H5N5/c1-2-5(4-7-3-1)6-8-10-11-9-6/h1-4H,(H,8,9,10,11)

InChIKey

SECHDFHDDVELCV-UHFFFAOYSA-N

SMILES

C1=NC=CC=C1C1=NNN=N1

CAS DataBase Reference

3250-74-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36/37/39-36

WGK Germany 

3

HazardClass 

IRRITANT-HARMFUL

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-(2H-TETRAZOL-5-YL)-PYRIDINE Chemical Properties,Usage,Production

Uses

5-(3-Pyridyl)-1H-tetrazole is used as a pharmaceutical intermediate. The Pyridine,3-(2H-tetrazol-5-yl)- acts as reactant with 1-(4-bromo-phenyl)-3-piperidino-propan-1-one, hydrochloride, and obtain the 1-(4-bromo-phenyl)-3-(5-pyridin-3-yl-tetrazol-2-yl)-propan-1-one. This reaction needs the solvent of dimethylformamide. The yield is 31%. In addition, this reaction should be taken for 8 hours at the temperature of 150°C.

Synthesis

The general procedure for the synthesis of 5-(3-pyridinyl)-1H-tetrazole from 3-cyanopyridine was as follows: 3-cyanopyridine (2 mmol), sodium azide (2.4 mmol, 1.2 eq.), and tetrabutylammonium bromide (2.4 mmol, 1.2 eq.) were added to a vial with a screw cap. The reaction mixture was stirred at 105 °C and the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature and dissolved in deionized water (5 mL). Subsequently, the aqueous solution was acidified with 1 M hydrochloric acid to pH = 3. If precipitate formation was observed, the suspension was filtered and the filter cake was washed with deionized water to obtain a pure product. If no precipitate formation was observed, the aqueous solution was extracted with ethyl acetate (3 x 4 mL). The organic phases were combined, washed with 1 M hydrochloric acid (3 x 4 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the pure product.

References

[1] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 4, p. 913 - 922
[2] Polyhedron, 2011, vol. 30, # 15, p. 2606 - 2610
[3] Mendeleev Communications, 2011, vol. 21, # 6, p. 334 - 336
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 2, p. 436 - 441
[5] European Journal of Organic Chemistry, 2014, vol. 2014, # 2, p. 436 - 441