4,4'-Methylenebis(2,6-dimethylaniline) Chemical Properties

Melting point:

121-123 °C(lit.)

Boiling point:

424.9±40.0 °C(Predicted)

Density 

1.066±0.06 g/cm3(Predicted)

vapor pressure 

0Pa at 20℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

5.05±0.25(Predicted)

Water Solubility 

27.02mg/L at 20℃

LogP

2.6 at 25℃

CAS DataBase Reference

4073-98-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

6.1

HS Code 

29029090

MSDS

• Language:English Provider:SigmaAldrich

4,4'-Methylenebis(2,6-dimethylaniline) Usage And Synthesis

Chemical Properties

Off-white powder

Flammability and Explosibility

Not classified

Synthesis

To a mixed solution of 2,6-dimethylaniline (10.00 g, 0.083 mol) and formaldehyde (4.03 g, 0.054 mol, 0.65 equiv) was slowly added dilute hydrochloric acid (2.2 ml, 0.1 M). The reaction mixture was stirred at 70 °C overnight. After completion of the reaction, the dark red solution was cooled to room temperature and diluted with dichloromethane (15 ml). Subsequently, a minimum amount of concentrated hydrochloric acid (2 ml) was added dropwise to the solution and stirring was continued for 2 h at room temperature followed by filtration. The resulting white salt was washed well with dichloromethane and dried in air. The dried salt was suspended in ether (70 ml), saturated aqueous sodium hydroxide solution was added and stirred until the solid was completely dissolved. The aqueous phase was extracted with ether (2 x 70 ml), the organic phases were combined, dried with magnesium sulfate, filtered and concentrated under reduced pressure to afford the target product 4-(4-amino-3,5-dimethylbenzyl)-2,6-dimethylaniline (2a) as an orange solid (8.97 g, 86% yield).

References

[1] Russian Journal of Organic Chemistry, 2009, vol. 45, # 4, p. 528 - 535
[2] Patent: WO2005/118605, 2005, A1. Location in patent: Page/Page column 107
[3] Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 5, p. 319 - 326
[4] Monatshefte fuer Chemie, 1898, vol. 19, p. 641
[5] Journal of Materials Chemistry, 1999, vol. 9, # 7, p. 1425 - 1429

4,4'-Methylenebis(2,6-dimethylaniline)(4073-98-7)Related Product Information

• 2,6-Diethylaniline
• 2,5-Dimethoxyaniline
• Benzyltrimethylammonium chloride
• 2,6-Diisopropylaniline
• 3,5-Bis(trifluoromethyl)aniline
• 4,4'-Methylenedianiline
• 3,5-Dimethylaniline
• 2,6-Dimethylaniline
• 3,5-Dimethoxyaniline
• N-Phenylbenzylamine
• DIMETHYLANILINE
• N,N-Dimethylaniline
• N,N-Dimethyl-1,4-phenylenediamine
• 4'-Aminoacetanilide
• 2,5-Dimethylaniline
• Dibenzoylmethane
• Tris(hydroxymethyl)aminomethane
• Benzyl chloride