4-IODO-2-METHYLANILINE Chemical Properties

Melting point:

86-89 °C (lit.)

Boiling point:

278.4±28.0 °C(Predicted)

Density 

1.791±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.66±0.10(Predicted)

color 

Purple to Dark purple to Dark red

Sensitive 

Light Sensitive

BRN 

2353618

InChI

InChI=1S/C7H8IN/c1-5-4-6(8)2-3-7(5)9/h2-4H,9H2,1H3

InChIKey

BGKLFAQCHHCZRZ-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(I)C=C1C

CAS DataBase Reference

13194-68-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-26,36/37/39

RIDADR 

2811

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214300

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-IODO-2-METHYLANILINE Usage And Synthesis

Chemical Properties

Grey to purple crystals

Synthesis

General procedure for the synthesis of 4-iodo-2-methylaniline from 2-methyl-4-bromoaniline: the aromatic Finkelstein reaction is used. Since copper(I) iodide is sensitive to moisture and oxygen, the reaction is carried out under argon protection using the standard Schlenk technique. The procedure is as follows: 2-methyl-4-bromoaniline, NaI (2 equiv., relative to bromine exchange) and CuI (5 mol%, relative to bromine exchange) are added to a two-necked pear-shaped flask equipped with a reflux condenser. N,N'-dimethylethylenediamine (L1) or N,N'-dimethyl-1,2-cyclohexanediamine (L2) (10 mol%, relative to bromine exchange) and anhydrous 1,4-dioxane (0.5 mL per 1 mmol NaI) were subsequently added. The resulting suspension was heated to 110°C and reacted for 18 hours. After completion of the reaction, it was cooled to room temperature and the mixture was poured into a 25% ammonia solution. The blue solution was diluted with deionized water until doubled in volume and extracted three times with dichloromethane. If 2,2'-bipyridine was used as the ligand, the combined organic phases were additionally washed with aqueous EDTA; otherwise, the combined organic phases were washed with saturated saline only and dried with anhydrous magnesium sulfate. The solvent is removed by concentration under reduced pressure to give pure 4-iodo-2-methylaniline. If necessary, the crude product can be further purified by column chromatography or recrystallization.

Purification Methods

Crystallise it from 50% EtOH. [Beilstein 12 IV 1807.]

References

[1] Synthesis (Germany), 2014, vol. 46, # 8, p. 1085 - 1090
[2] Journal of the American Chemical Society, 2015, vol. 137, # 26, p. 8328 - 8331

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