N-Boc-propargylamine Chemical Properties

Melting point:

40-44 °C

Boiling point:

170°C/14mmHg(lit.)

Density 

0.990±0.06 g/cm3(Predicted)

Flash point:

93°(199°F)

storage temp. 

2-8°C

solubility 

Soluble in chloroform.

pka

11.24±0.46(Predicted)

form 

Solid

color 

Pale Yellow to Dark Yellow

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C8H13NO2/c1-5-6-9-7(10)11-8(2,3)4/h1H,6H2,2-4H3,(H,9,10)

InChIKey

DSPYCWLYGXGJNJ-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-52/53

Safety Statements 

26-36/37-61

RIDADR 

UN3259

WGK Germany 

3

HazardClass 

8

HS Code 

2924297099

N-Boc-propargylamine Usage And Synthesis

Chemical Properties

Pale Yellow Low Melting Solid

Uses

N-Boc-propargylamine is used in the preparation of triazolobenzylidene-thiazolopyrimidines which act as CDC25 phosphatase inhibitors. Also used in the synthesis of β-glucan polysaccharide analogs.

Uses

N-Boc-propargylamine is used to prepare triazolobenzylidene-thiazolopyrimidines. which act as CDC25 phosphatase inhibitors. Further, it is used for the synthesis of beta-glucan polysaccharide analogs. In addition to this, it is involved in the Pauson-Khand (PK) reaction of norbornadiene and N-Boc-propargylamine to prepare 4,5-disubstituted cyclopentenones .

Synthesis

Di-tert-butyl dicarbonate (17.5 g, 80.0 mmol, 1.0 eq.) was slowly added dropwise to a dichloromethane solution (160 mL) of propargylamine (5.49 mL, 80.0 mmol, 1.0 eq.) at 0 °C. The reaction mixture was stirred at 0 °C for 1 h before the solvent was removed by distillation under reduced pressure. The resulting colorless oil was dried overnight under high vacuum to afford N-Boc-aminopropargyl (12.4 g, quantitative yield) as a white solid, which can be used in subsequent reactions without further purification. The spectral data of the product were consistent with those reported in the literature: Rf = 0.38 (hexane/ethyl acetate, 9:1); melting point = 41-42 °C (literature value:[1] 40-44 °C).1H NMR (500 MHz, CDCl3): δ (ppm) 4.94 (broad peak, 1H), 3.91 (broad double peak, J = 2.5 Hz, 2H), 2.23 (triple peak, J = 2.5 Hz, 1H). 2.5Hz, 1H), 1.45 (single peak, 9H).13C NMR (126MHz, CDCl3): δ (ppm) 155.2, 80.1, 79.9, 71.1, 28.2.

References

[1] Tetrahedron Letters, 2011, vol. 52, # 17, p. 2199 - 2202
[2] Organic Letters, 2014, vol. 16, # 9, p. 2430 - 2433
[3] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 7091 - 7113
[4] Patent: US2004/254231, 2004, A1
[5] Angewandte Chemie - International Edition, 2011, vol. 50, # 6, p. 1338 - 1341

N-Boc-propargylamine(92136-39-5)Related Product Information

• Propargyl bromide
• N-BOC-piperidine-4-carboxylic acid
• Diazomethane
• Methyl propiolate
• Bis(2-ethylhexyl)amine
• Aniline
• 3-Chloropropyne
• Propiolic Acid
• 3-Amino-1,2-propanediol
• :(S)-2-Methyl-3-(2-propynyl)-4-oxocyclopent-2-enyl-(lR)-cis,trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
• PROPARGYLAMINE
• Ethyl propiolate
• DI-TERT-BUTYL ETHER
• Propargyl alcohol
• rich-d-t-Prallethrin
• N-Boc-propargylamine