ChemicalBook Product Catalog Organic Chemistry Amides Naphthenic amines derivatives 4-Bromo-1,2-benzenediamine

4-Bromo-1,2-benzenediamine

Product Name4-Bromo-1,2-benzenediamine
CAS1575-37-7
MFC6H7BrN2
MW187.04
EINECS
MOL File1575-37-7.mol

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.
pka	3.46±0.10(Predicted)
form	powder to crystal
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
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

White solid

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.

Uses

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

General Description

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

Synthesis

875-51-4

1575-37-7

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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