Sodium Azide

Japan

TCI Practical Example: Tetrazole ring building reaction Used Chemicals 4-Bromobenzonitrile [B1426] Sodium Azide [S0489] Triethylamine Hydrochloride (= Et3N·HCl) [T0425] Toluene Procedure Sodium azide (139 mg, 2.14 mmol, 1.3 eq.) in toluene (3 mL) was added to a solution of 4-bromobenzonitrile (300 mg, 1.65 mmol) and triethylamine hydrochloride (295 mg, 2.14 mmol, 1.3 eq.) at room temperature. The mixture was stirred at 100 °C for 4 hours. Triethylamine hydrochloride (295 mg, 2.14 mmol, 1.3 eq.) and sodium azide (139 mg, 2.14 mmol, 1.3 eq.) were added and stirred overnight at the same temperature. Then the reaction mixture was quenched with water (15 mL) and the aqueous layer was washed with ethyl acetate (15 mL x 2) and was removed under reduced pressure and the residue was purified by column chromatography (on silica gel, dichloromethane:methanol = 5:1) and washed with acetonitrile:water (1:1, 6 mL) to give 5-(4-bromophenyl)-1H-tetrazole as a white solid (240 mg, 65% yield). Experimenter’s Comments The reaction mixture was monitored by UPLC. The reaction was performed in a fume hood because hydrogen azide may be generated. Analytical Data 5-(4-Bromophenyl)-1H-tetrazole 1H NMR (400 MHz, CDCl3); δ 7.99 (d, J = 8.0 Hz, 2H), 7.84 (d, J = 8.0 Hz, 2H). Lead Reference (S)-5-PYRROLIDIN-2-YL-1H-TETRAZOLE V. Aureggi, V. Franckevicius, M. O. Kitching, S. V. Ley, D. A. Longbottom, A. J. Oelke, G. Sedelmeier, Org. Synth. 2008, 85, 72. Application Versatile Azidation Reagent

MFCD00003536

87558449.0

1209320.0

GHS05, GHS06, GHS08, GHS09

Danger

H300 + H310 : Fatal if swallowed or in contact with skin. H314 : Causes severe skin burns and eye damage. H370 : Causes damage to organs. H372 : Causes damage to organs through prolonged or repeated exposure. H373 : May cause damage to organs through prolonged or repeated exposure. H410 : Very toxic to aquatic life with long lasting effects.

P501 : Dispose of contents/ container to an approved waste disposal plant. P273 : Avoid release to the environment. P260 : Do not breathe dust/ fume/ gas/ mist/ vapors/ spray. P270 : Do not eat, drink or smoke when using this product. P262 : Do not get in eyes, on skin, or on clothing. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection. P391 : Collect spillage. P307 + P311 : IF exposed: Call a POISON CENTER or doctor/ physician. P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower. P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P362 : Take off contaminated clothing and wash before reuse. P301 + P310 + P330 : IF SWALLOWED: Immediately call a POISON CENTER/doctor. Rinse mouth. P302 + P350 + P310 : IF ON SKIN: Gently wash with plenty of soap and water. Immediately call a POISON CENTER or doctor/ physician. P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor. P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor. P405 : Store locked up.

JY8050000

6.1

II

UN1687

8581.0

For laboratory research and development purposes only.

>99.0%(T)

Solid

65.01

Fukaya factory is certified for GMP, ISO14001:2004 (JQA-EM5386) and IQ Net (JP-JQA-EM5386).

White to Almost white powder to crystaline

NaN3

2850.00.5000

>99.0%(T)