2-Fluoro-4-iodoaniline

2-Fluoro-4-iodoaniline Property

Melting point:

55-57 °C (lit.)

Boiling point:

248.6±25.0 °C(Predicted)

Density 

2.008±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

2.41±0.10(Predicted)

form 

Powder

color 

Off-white to brown

Water Solubility 

insoluble

Sensitive 

Light Sensitive

BRN 

2081100

InChIKey

CUMTUBVTKOYYOU-UHFFFAOYSA-N

LogP

2.680 (est)

CAS DataBase Reference

29632-74-4(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,T,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-37/39-26/37/39

RIDADR 

PG3

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

IRRITANT-HARMFUL, LIGHT SENSITIVE

HS Code 

29214200

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

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

P405Store locked up.

P501Dispose of contents/container to..…

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

Chemical Properties

off-white to brown powder

Uses

2-Fluoro-4-iodoaniline is widely used in the pharmaceutical, chemical and food industries as a fundamental building block to create a variety of important compounds.

General Description

The profiling of iodine-containing metabolites produced by the earthworm Eisenia veneta by exposing it to 2-fluoro-4-iodoaniline was carried out using high-performance liquid chromatography/inductively coupled plasma mass spectrometry (HPLC/ICPMS).

Synthesis

The general procedure for the synthesis of 2-fluoro-4-iodoaniline from o-fluoroaniline is as follows: o-fluoroaniline (54 g, 486 mmol) was added to an aqueous solution (250 mL) of sodium bicarbonate (41 g, 486 mmol) with vigorous stirring. The suspension was heated to 60 °C in an oil bath and iodine (123 g, 486 mmol) was added in batches. After addition, the dark-colored mixture was continued to be stirred at 60°C for 3 hours. After completion of the reaction, it was cooled to room temperature and dichloromethane (300 mL) was added, followed by saturated sodium bisulfite solution (300 mL). The two-phase system was stirred vigorously for 10 minutes. The mixture was transferred to a 2L separatory funnel and the organic layer was separated. The aqueous layer was further extracted with dichloromethane (3 x 200 mL) and the combined organic phases were washed with brine (200 mL) and dried over anhydrous sodium sulfate. After filtration, the solvent was removed under reduced pressure to give a black crystalline solid. Hexane (300 mL) was added to the solid and the mixture was heated to reflux. A hexane solution was poured from the black insoluble syrup. Upon cooling, the product crystallized from hexane as fine yellow needles. Final isolation afforded 65 g (274 mmol) of 2-fluoro-4-iodoaniline as a fine yellow solid in 56% yield with a melting point of 53°C. 1H NMR (400 MHz, CDCl3) δ 8.1 (t, J=8Hz, 1H), 7.4 (d, J=6Hz, 1H), 7.2 (d, J=6Hz, 1H).

References

[1] Journal of the Chemical Society. Perkin Transactions 2, 1999, # 3, p. 481 - 491
[2] Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 11 A, p. 1612 - 1624
[3] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2870 - 2873
[4] Patent: WO2004/41793, 2004, A1. Location in patent: Page 141
[5] Chemical Communications, 2014, vol. 50, # 17, p. 2136 - 2138