N-Boc-propargylamine

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CAS:92136-39-5
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CAS:92136-39-5
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N-Boc-propargylamine Basic information
Product Name:N-Boc-propargylamine
Synonyms:N-prop-2-ynylcarbamic acid tert-butyl ester;N-(tert-BUTOXYCARBONYL)PROPARGYLAMINE, 98%N-(tert-BUTOXYCARBONYL)PROPARGYLAMINE, 98%N-(tert-BUTOXYCARBONYL)PROPARGYLAMINE, 98%;N-(tert-Butoxycarbonyl)propargyl amine;N-Boc-propargylamine;(2-Propynyl)carbamic acid tert-butyl ester;N-(2-Propynyl)-carbamic acid tert-butyl ester;N-(2-Propynyl)carbamic acid tert-butyl ester;N-Propargylcarbamic acid tert-butyl ester
CAS:92136-39-5
MF:C8H13NO2
MW:155.19
EINECS:
Product Categories:API intermediates;Nitrogen Compounds;Organic Building Blocks;Protected Amines;N-BOC;Miscellaneous
Mol File:92136-39-5.mol
N-Boc-propargylamine Structure
N-Boc-propargylamine Chemical Properties
Melting point 40-44 °C
Boiling point 170°C/14mmHg(lit.)
density 0.990±0.06 g/cm3(Predicted)
Fp 93°(199°F)
storage temp. 2-8°C
solubility Soluble in chloroform.
form Solid
pka11.24±0.46(Predicted)
color Pale Yellow to Dark Yellow
Sensitive Moisture Sensitive
InChIInChI=1S/C8H13NO2/c1-5-6-9-7(10)11-8(2,3)4/h1H,6H2,2-4H3,(H,9,10)
InChIKeyDSPYCWLYGXGJNJ-UHFFFAOYSA-N
SMILESC(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
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
N-Boc-propargylamine Usage And Synthesis
Chemical PropertiesPale Yellow Low Melting Solid
UsesN-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.
UsesN-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

24424-99-5

PROPARGYLAMINE

2450-71-7

N-Boc-propargylamine

92136-39-5

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
Tag: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

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