N-CBZ-N,N-BIS(2-CHLOROETHYL)AMINE

N-CBZ-N,N-BIS(2-CHLOROETHYL)AMINE Property

Boiling point:

376.9±42.0 °C(Predicted)

Density 

1.245±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-1.78±0.70(Predicted)

Appearance

Colorless to light yellow Liquid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

N-CBZ-N,N-BIS(2-CHLOROETHYL)AMINE Chemical Properties,Usage,Production

Synthesis

Bis(2-chloroethyl)amine hydrochloride (5 g, 0.028 mol) was suspended in 30 ml of anhydrous dichloromethane under cooling in an ice water bath and stirring. Benzyl chloroformate (5.1 g, 0.03 mol) was added slowly dropwise with a controlled dropwise time of 10 min. Subsequently, triethylamine (6.46 g, 0.063 mol) was added dropwise over 1 hour. The reaction mixture was continued to be stirred at room temperature for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of water (10 ml) and stirring was continued for 15 minutes. The organic phase (dichloromethane layer) was separated and washed sequentially with 1M HCl (10 ml) and saturated saline (10 ml), dried anhydrically and concentrated under reduced pressure to give the oily target product benzyl bis(dichloroethyl)aminocarboxylate (7 g, 95.5% yield, 80% purity).

References

[1] Organic Letters, 2009, vol. 11, # 2, p. 449 - 452
[2] Patent: US2009/143582, 2009, A1. Location in patent: Page/Page column 8
[3] Patent: US2015/105384, 2015, A1. Location in patent: Paragraph 0174; 0175
[4] Patent: WO2016/57779, 2016, A2. Location in patent: Page/Page column 63
[5] Patent: KR2017/43091, 2017, A. Location in patent: Paragraph 0693-0696