4-BROMO-2-IODOANILINE Chemical Properties

Melting point:

69-72 °C(lit.)

Boiling point:

297.9±30.0 °C(Predicted)

Density 

2.292±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

soluble in Methanol

pka

1.83±0.10(Predicted)

form 

Powder

color 

Gray to purple

InChI

InChI=1S/C6H5BrIN/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2

InChIKey

HHTYEQWCHQEJNV-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(Br)C=C1I

CAS DataBase Reference

66416-72-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,N,Xi

Risk Statements 

25-37/38-41-51/53

Safety Statements 

26-36/37/39-45-61

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29214200

MSDS

• Language:English Provider:SigmaAldrich

4-BROMO-2-IODOANILINE Usage And Synthesis

Chemical Properties

Grey to purple powder

Uses

4-Bromo-2-iodoaniline may be used in the following:

• Preparation of quinolone derivatives.
• Synthesis of a resin-bound sulfonamide, which was used as a starting material for the preparation of 2,3,5-trisubstituted indoles.

General Description

4-Bromo-2-iodoaniline is a 2-iodoaniline derivative. It can be prepared by reacting 4-bromoaniline with iodine.

Synthesis

General procedure: Iodination of aryl amines was carried out under solvent-free conditions. DBDABCODCI (0.5 mmol) was co-milled with 4-bromoaniline (1 mmol) in a porcelain mortar at room temperature. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, ethyl acetate was added to the mixture and subsequently filtered. The organic layer was washed with 5% aqueous sodium thiosulfate and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the resulting crude product was purified by column chromatography, the eluent being a solvent mixture of ethyl acetate and hexane. The purified product was characterized by melting point determination and 1H NMR spectroscopy.

References

[1] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 2, p. 600 - 602
[2] Bulletin of the Chemical Society of Ethiopia, 2015, vol. 29, # 1, p. 157 - 162
[3] RSC Advances, 2018, vol. 8, # 54, p. 30761 - 30776
[4] Synthesis, 2008, # 13, p. 2039 - 2044
[5] Patent: US9212182, 2015, B2. Location in patent: Page/Page column 198; 199

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