5-BROMO-2-IODOANILINE

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CAS:64085-52-5
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5-BROMO-2-IODOANILINE Basic information
Uses
Product Name:5-BROMO-2-IODOANILINE
Synonyms:5-BROMO-2-IODOANILINE;5-Bromo-2-iodobenzenamine;BenzenaMine, 5-broMo-2-iodo-;5-Bromo-2-iodooaniline
CAS:64085-52-5
MF:C6H5BrIN
MW:297.92
EINECS:
Product Categories:Anilines, Amides & Amines;Bromine Compounds;Iodine Compounds
Mol File:64085-52-5.mol
5-BROMO-2-IODOANILINE Structure
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
pka1.46±0.10(Predicted)
form powder
color Light gold (hint of peach)
InChIInChI=1S/C6H5BrIN/c7-4-1-2-5(8)6(9)3-4/h1-3H,9H2
InChIKeyKISIGYZVSJKAEK-UHFFFAOYSA-N
SMILESC1(N)=CC(Br)=CC=C1I
Safety Information
HS Code 2921420090
MSDS Information
5-BROMO-2-IODOANILINE Usage And Synthesis
Uses5-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
4-bromo-1-iodo-2-nitrobenzene

112671-42-8

5-BROMO-2-IODOANILINE

64085-52-5

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 Preparation Products And Raw materials
Raw materials4-Bromo-2-nitroaniline-->4'-BROMO-2'-NITROACETANILIDE-->4'-Bromoacetanilide-->4-bromo-1-iodo-2-nitrobenzene-->2-Nitroaniline-->Iron-->Acetic acid-->Ethanol
Tag: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