TERT-BUTYL N,N-DIALLYLCARBAMATE

TERT-BUTYL N,N-DIALLYLCARBAMATE Property

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

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P233Keep container tightly closed.

P235Keep cool.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

TERT-BUTYL N,N-DIALLYLCARBAMATE Chemical Properties,Usage,Production

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