5-(2-BROMOPHENYL)-1H-TETRAZOLE Chemical Properties

Melting point:

182-184 °C(lit.)

Boiling point:

389.3±44.0 °C(Predicted)

Density 

1.8047 (rough estimate)

refractive index 

1.6700 (estimate)

storage temp. 

Sealed in dry,2-8°C

pka

3.78±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

BRN 

148567

CAS DataBase Reference

73096-42-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37

WGK Germany 

3

HS Code 

29339990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-(2-BROMOPHENYL)-1H-TETRAZOLE Usage And Synthesis

Uses

5-(2-BROMOPHENYL)-1H-TETRAZOLE is a heterocyclic organic compound that can be used as an extremely important intermediate in organic synthesis. It can be used to synthesize pharmaceutical, pesticide, and industrial foaming agent products.

Chemical Properties

white to off-white powder

General Description

5-(2-Bromophenyl)-1H-tetrazole is a 5-substituted 1H-tetrazole. It can be synthesized via silica supported sulfuric acid catalyzed [3+2] cycloaddition of nitriles and sodium azide. Copper-catalyzed reaction of 5-(2-bromophenyl)-1H-tetrazole with ethyl 2-cyanoacetate has been reported to afford ethyl 1,3-diaminoisoquinoline-4-carboxylate.

Synthesis

Step 2) Synthesis of 5-(2-bromophenyl)-1H-tetrazole: A mixture of 2-bromobenzonitrile (10.0 g, 0.055 mol), sodium azide (3.9 g, 0.060 mol), ammonium chloride (3.2 g, 0.060 mol), and N,N-dimethylformamide (DMF, 90 mL) was heated for 18 hours at 100 °C. After completion of the reaction, the mixture was concentrated, dissolved in water and adjusted to alkaline (pH 9) with 1N potassium hydroxide (KOH) solution. The aqueous phase was extracted with ether (the organic phase was discarded) and subsequently acidified with 2N hydrochloric acid (HCl). The precipitate precipitated was collected by filtration to afford 9.1 g (73% yield) of the target product, 5-(2-bromophenyl)-1H-tetrazole, as an off-white solid with melting point 179-181 °C. The 1H NMR (DMSO-d6) data were as follows: δ 7.56 (m, 2H), 7.69 (dd, J = 7.0 Hz, 2.1 Hz, 1H), 7.86 (dd, J = 7.6 Hz, 1.3 Hz, 1H).

References

[1] Patent: WO2017/59411, 2017, A1. Location in patent: Paragraph 00386
[2] Patent: WO2006/81807, 2006, A2. Location in patent: Page/Page column 20; 33-34
[3] Patent: EP838458, 1998, A1
[4] Research on Chemical Intermediates, 2017, vol. 43, # 12, p. 7365 - 7374
[5] Tetrahedron Letters, 2014, vol. 55, # 24, p. 3507 - 3510

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