4-Bromo-1,2-benzenediamine Chemical Properties

Melting point:

65-69 °C (dec.)(lit.)

Boiling point:

289.3±20.0 °C(Predicted)

Density 

1.697±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in chloroform.

form 

powder to crystal

pka

3.46±0.10(Predicted)

color 

White to Brown

InChI

InChI=1S/C6H7BrN2/c7-4-1-2-5(8)6(9)3-4/h1-3H,8-9H2

InChIKey

WIHHVKUARKTSBU-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(Br)C=C1N

CAS DataBase Reference

1575-37-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25-36/38-43

Safety Statements 

26-36/37-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29215110

MSDS

• Language:English Provider:SigmaAldrich

4-Bromo-1,2-benzenediamine Usage And Synthesis

Chemical Properties

White solid

Uses

4-Bromo-o-phenylenediamine, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

Uses

4-Bromo-1,2-diaminobenzene can be used as a precursor for preparing fluorescent dipolar quinoxaline derivatives, which can find applications as potential emissive and electron-transport materials. It can also be used in the synthesis of 6-bromo-2-methylbenzimidazole.

General Description

4-Bromo-1,2-diaminobenzene can be obtained from 1,2-diaminobenzene via acetylation followed by bromination and alkaline hydrolysis.

Synthesis

1. 4-Bromo-2-nitroaniline (600 mg, 2.76 mmol) was dissolved in 25 mL of anhydrous ethanol. 2. Stannous chloride (SnCl2, 2.72 g, 14 mmol) was added to the solution. 3. The reaction mixture was heated to reflux overnight. 4. 4. After completion of the reaction, the ethanol was removed by rotary evaporator under reduced pressure. 5. The residue was alkalized to pH 11 with 2 N sodium hydroxide solution. 6. The organic layer was collected by extraction with ether. 7. The organic layer was dried with anhydrous sodium sulfate. 8. After filtration, the organic layer was concentrated by rotary evaporator under reduced pressure to give the crude product 4-bromophthalimide (486 mg, 2.6 mmol, 94% yield). 9. The crude product was used directly in the next reaction without further purification.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 5, p. 827 - 832
[2] Australian Journal of Chemistry, 1983, vol. 36, # 11, p. 2317 - 2325
[3] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 11, p. 2591 - 2600
[4] Patent: US6063801, 2000, A
[5] Journal of Organic Chemistry, 2007, vol. 72, # 9, p. 3186 - 3193

4-Bromo-1,2-benzenediamine(1575-37-7)Related Product Information

• m-Phenylenediamine
• p-Phenylenediamine
• o-Phenylenediamine
• Pentabromodiphenyl ether
• Decabromodiphenyl Ethane
• 4-BROMOCATECHOL
• 4-Bromo-2-nitroaniline
• 5-BROMO-3,4-DIMETHYLBENZENE-1,2-DIAMINE
• Bromine
• 4'-BROMO-2'-NITROACETANILIDE
• 2,4-Dibromo-6-nitroaniline
• 4-BROMO-2,3-DIMETHYL-6-NITROANILINE
• 3,5-DIBROMO-1,2-PHENYLENEDIAMINE MONOHYDROCHLORIDE
• 1-ACETYL-5-BROMO-7-NITROINDOLINE
• 5-Bromo-7-nitroindoline
• 4-Bromo-2-methyl-6-nitroaniline
• N-(2-amino-4-bromophenyl)acetamide
• BUTTPARK 45\01-52