5-IODO-2-METHYLANILINE Chemical Properties

Melting point:

48-52 °C (lit.)

Boiling point:

273 °C/760 mmHg (lit.)

Density 

1.7004 (estimate)

Flash point:

110 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.49±0.10(Predicted)

color 

Light yellow to Brown to Dark green

Sensitive 

Light Sensitive

BRN 

2078769

CAS DataBase Reference

83863-33-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25-37/38-41-43

Safety Statements 

26-36/37-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

2921420090

MSDS

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

5-IODO-2-METHYLANILINE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 5-iodo-2-methylaniline from 4-iodo-2-nitrotoluene was as follows: to a 300 mL ethanol solution of 4-iodo-1-methyl-2-nitrobenzene (25.0 g, 107 mmol) was added platinum sulfide (3.00 g) and ammonium formate (20.3 g, 321 mmol). The reaction mixture was heated to reflux and maintained for 12 hours. Upon completion of the reaction, the mixture was cooled to 22 °C and filtered through a Celite pad to remove solid impurities. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was diluted with 300 mL of water and subsequently extracted with dichloromethane (3 x 200 mL). The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. Finally, the organic phase was concentrated under reduced pressure to afford the target product 5-iodo-2-methylaniline (21.1 g, 95% yield). Mass spectrometry analysis showed MS m/z = 234 (M + H).

References

[1] Patent: WO2006/41773, 2006, A2. Location in patent: Page/Page column 302-303
[2] Patent: WO2010/127855, 2010, A1. Location in patent: Page/Page column 121; 122
[3] Justus Liebigs Annalen der Chemie, 1871, vol. 158, p. 337

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