2-(N-BOC-METHYLAMINO)ACETONITRILE Chemical Properties

Boiling point:

244.5±19.0 °C(Predicted)

Density 

1.033±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-1.91±0.70(Predicted)

Appearance

Light brown to yellow Liquid

InChI

InChI=1S/C8H14N2O2/c1-8(2,3)12-7(11)10(4)6-5-9/h6H2,1-4H3

InChIKey

AXNPHDXTYKKHSJ-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)N(CC#N)C

Safety Information

HS Code 

2926907090

2-(N-BOC-METHYLAMINO)ACETONITRILE Usage And Synthesis

Synthesis

GENERAL STEPS: To a dichloromethane (DCM, 100 mL) suspension of 2-methylaminoacetonitrile hydrochloride (11.45 g, 107.4 mmol) was added triethylamine (31.5 mL, 226 mmol), followed by the slow addition of di-tert-butyl dicarbonate (22.3 g, 102.2 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was filtered to remove insoluble salts and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using a 10-20% ethyl acetate/cyclohexane gradient elution. Fractions containing the target product were collected, combined and concentrated under reduced pressure to give tert-butyl (cyanomethyl)(methyl)carbamate (11.94 g, 69% yield) as a colorless liquid.LC-MS (Method 5): retention time 2.82 min, [M + H]+ m/z 171.1.

References

[1] Journal of Medicinal Chemistry, 1996, vol. 39, # 16, p. 3070 - 3088
[2] Patent: WO2008/23157, 2008, A1. Location in patent: Page/Page column 115

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