4-Iodo-N,N-dimethyl-Benzenamine

4-Iodo-N,N-dimethyl-Benzenamine Property

Melting point:

79.5 °C

Boiling point:

263.7±23.0 °C(Predicted)

Density 

1.652±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

pka

4.14±0.12(Predicted)

color 

Very Dark Blue to Very Dark Purple

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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.

P310Immediately call a POISON CENTER or doctor/physician.

4-Iodo-N,N-dimethyl-Benzenamine Chemical Properties,Usage,Production

Uses

4-Iodo-N,N-dimethylaniline is a useful reactant for organic reactions and the synthesis of various compounds.

Synthesis

General procedure for the synthesis of 4-N,N-dimethylaminoiodobenzene from N,N-dimethylaniline: to a stirred solution of N,N-dimethylaniline (1 mmol) in dichloromethane (CH2Cl2) or 1,2-dichloroethane ((CH2Cl)2) (0.1 M) was added sequentially Ph3PAuNTf2 (0.025 mmol, 19 mg; if using the 2:1 complex of Ph3PAuNTf2 with toluene) and N-iodosuccinimide (NIS, 1.1 mmol, 248 mg). The reaction mixture was stirred at room temperature or reacted under reflux conditions until complete conversion of the feedstock was shown by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the resulting crude product was purified by fast column chromatography using different ratios of hexane and ethyl acetate (EtOAc) as eluents, resulting in pure 4-N,N-dimethylaminoiodobenzene.

References

[1] RSC Advances, 2014, vol. 4, # 12, p. 6267 - 6274
[2] Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2058 - 2060
[3] Tetrahedron Letters, 2005, vol. 46, # 32, p. 5421 - 5423
[4] Tetrahedron, 2005, vol. 61, # 49, p. 11657 - 11663
[5] Helvetica Chimica Acta, 2007, vol. 90, # 11, p. 2087 - 2095