5-BROMO-2-IODOANILINE Chemical Properties

Melting point:

55 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))

Boiling point:

309.5±27.0 °C(Predicted)

Density 

2.292±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

pka

1.46±0.10(Predicted)

form 

powder

color 

Light gold (hint of peach)

InChI

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

InChIKey

KISIGYZVSJKAEK-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2921420090

5-BROMO-2-IODOANILINE Usage And Synthesis

Uses

5-Bromo-2-iodoaniline can be used as a pharmaceutical and chemical synthesis intermediate. If 5-Bromo-2-iodoaniline is inhaled, move the patient to fresh air; if skin contact occurs, remove contaminated clothing and thoroughly wash the skin with soap and water. If discomfort persists, seek medical attention.

Synthesis

The general procedure for the synthesis of 5-bromo-2-iodoaniline from 4-bromo-1-iodo-2-nitrobenzene was as follows: 4-bromo-1-iodo-2-nitrobenzene (8.38 g, 109.6 mmol) was dissolved in a mixed solvent of acetic acid (AcOH, 45 mL) and ethanol (EtOH, 45 mL) at room temperature, followed by the addition of powdered iron (Fe, 6.12 g 109.6 mmol). The reaction mixture was heated to 100 °C and stirred for 1.3 h, after which it was cooled to room temperature. The reaction mixture was diluted with ether (Et2O, 90 mL) and washed with saturated aqueous sodium bicarbonate (NaHCO3) solution (200 mL). The organic layer was separated and the aqueous layer was further extracted with ether (3 x 60 mL). All organic layers were combined, washed with brine (300 mL), dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure. The residue was purified by fast column chromatography (silica gel as stationary phase, hexane/ethyl acetate=19:1 as eluent) to afford the target product 5-bromo-2-iodoaniline (6.89 g, 91% yield) as a light yellow solid.

References

[1] Heterocycles, 2009, vol. 79, # C, p. 805 - 820
[2] Tetrahedron, 2013, vol. 69, # 45, p. 9481 - 9493
[3] Synthesis, 2008, # 13, p. 2039 - 2044
[4] Chemical & Pharmaceutical Bulletin, 1987, vol. 35, # 5, p. 1823 - 1828
[5] Patent: WO2011/119860, 2011, A1. Location in patent: Page/Page column 90

5-BROMO-2-IODOANILINE(64085-52-5)Related Product Information

• 4'-Bromoacetanilide
• 2-Bromoaniline
• 2,4,6-Tribromoaniline
• 2,2-Dimethyl-1,3-propanediol
• 5-BROMO-2-IODOANILINE
• (5-bromo-2-iodophenyl)methanamine