2,4,5-Tribromoimidazole

2,4,5-Tribromoimidazole Property

Melting point:

217-220 °C (dec.) (lit.)

Boiling point:

401.3±48.0 °C(Predicted)

Density 

3.8211 (rough estimate)

refractive index 

1.6500 (estimate)

storage temp. 

2-8°C

form 

Powder

pka

6.32±0.10(Predicted)

color 

Beige-yellow

BRN 

115314

InChIKey

JCGGPCDDFXIVQB-UHFFFAOYSA-N

CAS DataBase Reference

2034-22-2(CAS DataBase Reference)

NIST Chemistry Reference

Imidazole, 2,4,5-tribromo-(2034-22-2)

Safety

Hazard Codes 

T,Xi

Risk Statements 

23/24/25-36/37/38-25

Safety Statements 

22-26-36/37/39-45

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

NI8660000

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

II

HS Code 

29332990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H300Fatal if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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

2,4,5-Tribromoimidazole Chemical Properties,Usage,Production

Application

2,4,5-Tribromoimidazole is an organic intermediate that can be obtained by brominating imidazole. 2,4,5-Tribromoimidazole can be debrominated to give 4,5-dibromoimidazole.

Chemical Properties

BEIGE-YELLOW POWDER

General Description

2,4,5-Tribromoimidazole(2,4,5-TBI) on condensation with sugar precursors yields 2,4,5-TBI nucleosides.

Biochem/physiol Actions

2,4,5-Tribromoimidazole induces poisoning typical of uncouplers of oxidative phosphorylation in rats.

Synthesis

The general procedure for the synthesis of 2,4,5-tribromoimidazole from imidazole was as follows: to a three-necked flask equipped with a thermostatic separatory funnel was added imidazole (29.24 g, 0.43 mol), sodium acetate (317.34 g, 3.87 mol) and acetic acid (150 mL). The mixture was dissolved in additional acetic acid (100 mL). Bromine (65 mL, 1.28 mol) was added slowly dropwise through a thermostatic separatory funnel at room temperature, controlling the reaction temperature to not exceed 40°C. After the dropwise addition was completed, the reaction mixture continued to be stirred for 3 hours at room temperature. Upon completion of the reaction, the reaction solution was poured into 1.5 L of water to induce precipitation of the solid product. The solid product was collected by filtration and washed several times with water to remove impurities. Finally, the solid product was dried to afford the target compound 2,4,5-tribromoimidazole (120 g, 92% yield).

References

[1] Patent: CN106256830, 2016, A. Location in patent: Paragraph 0044; 0049; 0050; 0051
[2] Tetrahedron Letters, 2015, vol. 56, # 41, p. 5646 - 5650
[3] Tetrahedron Letters, 1998, vol. 39, # 44, p. 8163 - 8166
[4] Tetrahedron, 1999, vol. 55, # 4, p. 935 - 942
[5] Journal of Organic Chemistry, 1992, vol. 57, # 9, p. 2740 - 2741