2-IODO-4-METHYLANILINE Chemical Properties

Melting point:

34-37°C

Boiling point:

273°C (rough estimate)

Density 

1.7004 (estimate)

Flash point:

>110°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

2.97±0.10(Predicted)

form 

crystalline powder

color 

cream

InChIKey

AJTUKWIQLKKRHE-UHFFFAOYSA-N

CAS DataBase Reference

29289-13-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

36/37/38-41-37/38-25

Safety Statements 

26-37/39-36/37/39-27-45

RIDADR 

2811

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29214300

2-IODO-4-METHYLANILINE Usage And Synthesis

Chemical Properties

Milky white solid

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 899, 1989 DOI: 10.1016/S0040-4039(00)95273-0

Synthesis

Step 1: Preparation of 2-iodo-4-methylaniline To a solution of 4-methylaniline (53.5 g, 500 mmol) in dichloromethane (DCM, 200 mL) was added a solution of sodium bicarbonate (NaHCO3, 50.4 g) in water (500 mL) at room temperature, followed by iodine (I2, 127 g). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was treated with aqueous sodium bisulfite (NaHSO3) and extracted with dichloromethane (DCM). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give the brown oily product 2-iodo-4-methylaniline (110 g, 95% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.48 (dd, J = 1.8 and 0.6 Hz, 1H), 6.96 (dd, J = 8.1 and 1.8 Hz, 1H), 6.67 (d, J = 8.1 Hz, 1H), 3.98 (broad peak, 2H), 2.22 (s, 3H) ppm.

References

[1] Journal of Organic Chemistry, 1996, vol. 61, # 17, p. 5804 - 5812
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 15, p. 2640 - 2652
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 8, p. 897 - 904
[4] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 19, p. 2805 - 2810
[5] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 5, p. 1031 - 1038

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