2,2'-(BENZYLIMINO)DIETHANOL Chemical Properties

Melting point:

196.5 °C(Solv: benzene (71-43-2))

Boiling point:

226°C(lit.)

Density 

1.09

refractive index 

1.5370 to 1.5410

storage temp. 

Inert atmosphere,Room Temperature

form 

clear liquid

pka

14.39±0.10(Predicted)

color 

Colorless to Yellow to Orange

InChI

InChI=1S/C11H17NO2/c13-8-6-12(7-9-14)10-11-4-2-1-3-5-11/h1-5,13-14H,6-10H2

InChIKey

MIZIOHLLYXVEHJ-UHFFFAOYSA-N

SMILES

N(CCO)(CCO)CC1=CC=CC=C1

CAS DataBase Reference

101-32-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

RTECS 

KJ7538000

HazardClass 

IRRITANT

HS Code 

2922190090

2,2'-(BENZYLIMINO)DIETHANOL Usage And Synthesis

Uses

2,2'-(Benzylazanediyl)diethanol is a useful research chemical.

Synthesis

General procedure for the synthesis of 2,2-(benzylimino)diethanol from benzyl bromide and diethanolamine: K2CO3 (8.65 g, 62.58 mmol) and benzyl bromide (2.96 g, 25 mmol) were added to anhydrous acetone (65 mL) followed by diethanolamine (2.63 g, 53.08 mmol). The reaction mixture was heated to reflux and the reaction was continued overnight. After completion of the reaction, the white suspension obtained was filtered and the solvent was removed by evaporation to obtain 5.6 g of yellow liquid. The liquid was dissolved in dichloromethane (DCM) and washed with deionized water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuum to give the final 2,2-(benzylimino)diethanol (4.88 g, 100% yield). The product was analyzed by HPLC-MS (Method A): retention time 1.14 min; ESI-MS m/z 196 ([M+H]+).

References

[1] Inorganic Chemistry, 2012, vol. 51, # 19, p. 10384 - 10393,10
[2] Patent: WO2017/16669, 2017, A1. Location in patent: Page/Page column 201
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 12, p. 2376 - 2396
[4] Patent: EP970046, 2003, B1. Location in patent: Page 45-46
[5] Patent: US6342508, 2002, B1. Location in patent: Page column 58-59

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