tert-Butyl 2-(aminomethyl)phenylcarbamate

tert-Butyl 2-(aminomethyl)phenylcarbamate Property

Boiling point:

238-242℃

Density 

1.054g/mLat 25℃

Flash point:

71°C

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

liquid

pka

13.67±0.70(Predicted)

Appearance

Off-white to light yellow Solid

Safety

Hazard Codes 

Xn

Risk Statements 

22-43

Safety Statements 

36/37

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

HS Code 

2921490090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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.

tert-Butyl 2-(aminomethyl)phenylcarbamate Chemical Properties,Usage,Production

Uses

Reactant for:

• Two-step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines employing a double UDC (Ugi/Deprotect/Cyclize) strategy
• Preparation of hydroquinazoline scaffolds via microwave-promoted Ugi reaction and cyclization
• Preparation of pyrazinone inhibitors of mast cell tryptase

Uses

Tert-Butyl 2-(aminomethyl)phenylcarbamate can be used as reactant for Two-step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines employing a double UDC (Ugi/Deprotect/Cyclize)

Synthesis

Example 1 Synthesis of tert-butyl N-[2-(aminomethyl)phenyl]carbamate: To an anhydrous dichloromethane (30 mL) solution of 2-aminobenzylamine (2.440 g, 20.0 mmol), an anhydrous dichloromethane (12 mL) solution of di-tert-butyl dicarbonate (4.360 g, 20.0 mmol) was slowly added dropwise over a period of minutes at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC) with ethyl acetate: hexane (1:1) as the unfolding agent, and the completion of the reaction was confirmed after about 30 minutes. Subsequently, the volatile solvent was removed by rotary evaporation, and the resulting solid was purified by fast column chromatography with the eluent ethyl acetate-hexane (initial ratio 1.5:8.5, gradually adjusted to 3:7), resulting in tert-butyl N-[2-(aminomethyl)phenyl]carbamate 3.912 g in 88% yield as an off-white powder, with spectral and analytical data as expected.

References

[1] Patent: US6927294, 2005, B1. Location in patent: Page/Page column 18