2,5-Dibromonitrobenzene Chemical Properties

Melting point:

82-84 °C (lit.)

Boiling point:

266.4°C (rough estimate)

Density 

2.374 g/mL at 25 °C (lit.)

refractive index 

1.6400 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Powder

color 

Yellow

Water Solubility 

Slightly soluble in water.

BRN 

1950425

InChI

InChI=1S/C6H3Br2NO2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H

InChIKey

WRGKKASJBOREMB-UHFFFAOYSA-N

SMILES

C1(Br)=CC=C(Br)C=C1[N+]([O-])=O

CAS DataBase Reference

3460-18-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-36/37/38-50-20/21/22

Safety Statements 

26-60-61-36/37/39-22

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

2

HazardClass 

9

HS Code 

29049090

MSDS

• Language:English Provider:1,4-Dibromo-2-nitrobenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,5-Dibromonitrobenzene Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2,5-Dibromonitrobenzene is a halogen-substituted nitrobenzenes used against Tetrahymena pyriformis due to its inhibitory and toxicity activities.

Synthesis

The general procedure for the synthesis of 2,5-dibromonitrobenzene from 1,4-dibromobenzene was as follows: a mixture of nitric acid (90%, 4.6 g, 70 mmol) and concentrated sulfuric acid (75 mL) was slowly added dropwise to a solution of dichloromethane (30 mL) and concentrated sulfuric acid (20 mL) containing 1,4-dibromobenzene (11.8 g, 50 mmol), with the use of a dropping funnel during the addition. The acceleration of the drop was controlled and the reaction was carried out at room temperature for 20 min. After completion of the reaction, stirring of the reaction mixture was continued for 30 min. Subsequently, the reaction was quenched with 25% aqueous sodium hydroxide solution (3 mL), the reaction product was extracted with dichloromethane (30 mL) and the aqueous layer was washed with dichloromethane (10 mL). The organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure to give the light yellow crystalline product 2,5-dibromonitrobenzene (13.7 g, 97% yield) with a melting point of 83-84°C. The product was extracted by 1H NMR and the aqueous layer was washed with dichloromethane (10 mL). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3), δ 7.98 (d, J = 2.3 Hz, 1H), 7.55-7.63 (m, 2H).

Purification Methods

It crystallises from Me2CO or EtOH. [Beilstein 5 H 250, 5 II 190, 5 III 621, 5 IV 732.]

References

[1] Tetrahedron, 2004, vol. 60, # 1, p. 81 - 92
[2] European Journal of Organic Chemistry, 2012, # 36, p. 7066 - 7074
[3] Dyes and Pigments, 2013, vol. 96, # 3, p. 619 - 625
[4] Journal of Materials Chemistry C, 2016, vol. 4, # 23, p. 5448 - 5460
[5] Organic Letters, 2001, vol. 3, # 7, p. 993 - 995

2,5-Dibromonitrobenzene(3460-18-2)Related Product Information

• 4-Nitrobenzaldehyde
• Sodium 3-nitrobenzenesulphonate
• 4-Nitrobenzoic acid
• 2,4-Dibromonitrobenzene
• 1,4-Dibromobenzene
• 3-Bromoaniline
• 1-Bromo-2-nitrobenzene
• 3-Bromonitrobenzene
• 2,5-Dibromobenzenamine
• 1,3-Dinitrobenzene
• Nitrobenzene
• 2-Bromoaniline
• 2,4-Dibromonitrobenzene
• 3,4-Dibromonitrobenzene
• 2,5-Dibromonitrobenzene
• ρ-Nitrobenzenesulphonic acid
• 4,7-DIBROMO-5-NITRO-2,1,3-BENZOTHIADIAZOLE
• 2,5-dibromo-3-nitrobenzenesulfonyl chloride