4-Chloro-2-iodoaniline

4-Chloro-2-iodoaniline Property

Melting point:

40 °C

Boiling point:

295.0±25.0 °C(Predicted)

Density 

2.015±0.06 g/cm3(Predicted)

Flash point:

>110 °C

storage temp. 

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

solubility 

soluble in Methanol

form 

Powder

pka

1.90±0.10(Predicted)

color 

White to off-white

Sensitive 

Light Sensitive

InChI

InChI=1S/C6H5ClIN/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2

InChIKey

FLEJOBRWKBPUOX-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

63069-48-7(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,N,T

Risk Statements 

20/21/22-36/37/38-51/53-41-37/38-25

Safety Statements 

26-36/37/39-61-45

RIDADR 

UN 2811

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214200

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-Chloro-2-iodoaniline Chemical Properties,Usage,Production

Uses

Iodinated aminoaryl compounds such as 2-iodo-4-chloroaniline are of considerable value as synthetic intermediates and can be used in a variety of industrial environments, including the pharmaceutical industry.

Chemical Properties

Pale brown to purple low melting solid

Synthesis

General method: 4-Chloroaniline (20.0 mmol) was dissolved in a solvent mixture of H2O (100 mL) and MeOH (300 mL) and the pH was adjusted to 1-2 by adding concentrated HCl (tested using pH paper). Subsequently, NaICl2 aqueous solution (50% w/w, 1.1-4.8 molar equivalents, see table for exact dosage) was slowly added dropwise and the reaction mixture was stirred for 3-4 hours at room temperature. Upon completion of the reaction, the reaction was quenched by adding saturated NaHSO3 aqueous solution until the starch test was negative. If no significant precipitate was generated in the reaction mixture, the pH was adjusted to alkaline by dropwise addition of 1 M NaOH aqueous solution (tested using pH paper), followed by extraction with Et2O. The organic phases were combined, dried with MgSO4, filtered and concentrated under reduced pressure to give the solid product. If a precipitate was generated in the reaction mixture, the solid was first separated by gravity filtration, then the filtrate was adjusted to slightly basic (using 1 M NaOH aqueous solution) and extracted with Et2O. The organic extracts were combined, dried with MgSO4, filtered and concentrated under reduced pressure to give the solid product. All solid products were analyzed by TLC (silica gel plates, different ratios of hexane/ethyl acetate as unfolding agent). If the products were mixtures, they were separated and purified by fast column chromatography (silica gel, hexane/ethyl acetate = 9:1, unless otherwise stated). The final products were characterized by melting point (compared to literature values), IR, MS, 1H-NMR, 13C-NMR spectra and elemental analysis (for new compounds). It should be noted that the reaction products of anilines 1a-1j are mostly known compounds, while theanisidines failed to yield characterizable products.

References

[1] Organic Preparations and Procedures International, 2016, vol. 48, # 5, p. 385 - 392
[2] Synlett, 2014, vol. 25, # 6, p. 831 - 834