N-(tert-Butoxycarbonyl)-2-aminoacetonitrile Chemical Properties

Melting point:

53-57 °C(lit.)

Boiling point:

186 °C(lit.)

Density 

1.1832 (rough estimate)

refractive index 

1.4880 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

9.96±0.46(Predicted)

form 

solid

color 

Brown

InChI

InChI=1S/C7H12N2O2/c1-7(2,3)11-6(10)9-5-4-8/h5H2,1-3H3,(H,9,10)

InChIKey

SMZKPZXYDDZDJG-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

85363-04-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36

WGK Germany 

3

HS Code 

2926907090

MSDS

• Language:English Provider:SigmaAldrich

N-(tert-Butoxycarbonyl)-2-aminoacetonitrile Usage And Synthesis

Uses

N-(tert-Butoxycarbonyl)-2-aminoacetonitrile may be used for the preparation of N-(tert-butoxycarbonyl)-2-aminoacetamidoxime, by reaction with hydroxylamine hydrochloride.

General Description

N-(tert-Butoxycarbonyl)-2-aminoacetonitrile is an organic building block.

Synthesis

The general procedure for the synthesis of 2-(Boc-amino)acetonitrile from di-tert-butyl dicarbonate and aminoacetonitrile sulfate was as follows: first, 3 mmol of aminoacetonitrile sulfate was dissolved in 50 mL of anhydrous methanol at room temperature and protected by nitrogen. Subsequently, 770 mg (4.5 mmol) of L-cysteine methyl ester hydrochloride and 0.63 mL (4.5 mmol) of triethylamine were added to this solution. The reaction mixture was stirred at room temperature for 3 hours, after which the solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane and washed sequentially with saturated sodium bicarbonate solution and brine. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated, and finally purified by silica gel column chromatography (eluent: hexane/ethyl acetate, 5:1) to afford a methyl ester derivative of the target product 2-(Boc-amino)acetonitrile. Next, 0.9 mL (0.9 mmol) of a 1N lithium hydroxide solution was added to 1.0 mmol of a 5 mL methanol solution of the above methyl ester derivative at 0 °C. The suspension was stirred at room temperature for 1 h. Upon completion of the reaction, it was diluted with 20 mL of acetone to promote precipitation of the product. The white solid was collected by filtration and dried to give purified 2-(Boc-amino)acetonitrile.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 19, p. 6229 - 6232
[2] Chemistry - A European Journal, 2018, vol. 24, # 68, p. 18075 - 18081

N-(tert-Butoxycarbonyl)-2-aminoacetonitrile(85363-04-8)Related Product Information

• Iminodiacetonitrile
• AMINOACETONITRILE HYDROGEN SULFATE
• DI-TERT-BUTYL ETHER
• Benzeneacetonitrile
• Boc-L-Ala-nitrile
• BOC-L-LEU-NITRILE
• (R)-1-Boc-2-cyanopyrrolidine
• (S)-BOC-2-AMINO-3-PHENYL-PROPIONITRILE
• Boc-L-Val-nitrile
• 2-(N-BOC-METHYLAMINO)ACETONITRILE
• AMINOACETONITRILE
• 1-Boc-2-cyanopiperidine
• (1-CYANO-CYCLOPENTYL)-CARBAMIC ACIDTERT-BUTYL ESTER
• 3-BOC-AMINOBUTYRONITRILE
• (1-CYANO-CYCLOHEPTYL)-CARBAMIC ACID TERT-BUTYL ESTER
• (R)-4-CYANO-THIAZOLIDINE-3-CARBOXYLIC ACID TERT-BUTYL ESTER
• (CYANO-PHENYL-METHYL)-CARBAMIC ACID TERT-BUTYL ESTER
• (S)-BOC-2-AMINO-3-(3-INDOLYL)-PROPIONITRILE