TERT-BUTYL N,N-DIALLYLCARBAMATE Chemical Properties

Boiling point:

75 °C/1.5 mmHg (lit.)

Density 

0.914 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.442(lit.)

Flash point:

81 °C

storage temp. 

2-8°C, stored under nitrogen

pka

-1.46±0.70(Predicted)

Appearance

Colorless to light yellow Liquid

Safety Information

WGK Germany 

3

TERT-BUTYL N,N-DIALLYLCARBAMATE Usage And Synthesis

Uses

tert-Butyl N,N-diallylcarbamate may be used in the synthesis of heterocyclic compounds.

General Description

tert-Butyl N,N-diallylcarbamate is a protected amine. Ring-closing metathesis (RCM) reactions of tert-butyl N,N-diallylcarbamate in the presence of Hoveyda-Grubbs type catalyst supported on mesoporous molecular sieves have been reported.

Synthesis

Example 5: (±)-trans-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-vinylpyrrolidine (1. X=vinyl, A=CH, B=NH, D=H); Example 5.1: tert-butyl diallylcarbamate (7); Di-tert-butyl dicarbonate (42.2 g, 193 mmol) was added batchwise to a solution of diallylamine (2) (20 mL, 162 mmol) in methanol (500 mL) at 0°C. After addition, the reaction mixture was gradually warmed to room temperature with continuous stirring for 1 hour. Subsequently, the reaction mixture was concentrated by distillation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate gradient elution, 0 to 50% ethyl acetate) to afford the target product tert-butyl diallylcarbamate 7 as a colorless oil (31.9 g, 99% yield). (Org. Biomol. Chem. 2004, 2, 2418-2420).

References

[1] Patent: WO2011/8110, 2011, A1. Location in patent: Page/Page column 41-42
[2] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8283 - 8286
[3] Synthesis, 2001, # 1, p. 46 - 48
[4] Synthesis, 2004, # 14, p. 2367 - 2375
[5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2016, vol. 71, # 6, p. 633 - 641

TERT-BUTYL N,N-DIALLYLCARBAMATE(151259-38-0)Related Product Information

• Diallylamine
• TERT-BUTYL N-ALLYLCARBAMATE
• TERT-BUTYL N,N-DIALLYLCARBAMATE