Identification | Back Directory | [Name]
TERT-BUTYL N-ALLYLCARBAMATE | [CAS]
78888-18-3 | [Synonyms]
N-BOC-AllylaMine N-Boc-3-aminopropene ert-Butylallylcarbamate N-ALLYL-T-BUTYLCARBAMATE tert-Butyl allylcarbamate TERT-BUTYL N-ALLYLCARBAMATE N-Tert-Butyl-Allylcarbamate tert-Butoxycarbonylallylamine tert-Butyl N-Allylcarbamate > tert-Butyl N-allylcarbaMate 98% N-(tert-Butoxycarbonyl)allylamine ALLYL-CARBAMIC ACID TERT-BUTYL ESTER N-Allylcarbamic acid tert-butyl ester 3-(tert-Butoxycarbonylamino)-1-propene N-tert-butoxycarbonylprop-2-en-1-amine tert-Butyl N-Allylcarbamate N-(tert-Butyloxycarbonyl)-2-propene-1-amine CarbaMic acid, N-2-propen-1-yl-, 1,1-diMethylethyl ester Carbamic acid, 2-propenyl-, 1,1-dimethylethyl ester (9CI) N-Boc-allylamine
N-(tert-Butoxycarbonyl)allylamine
N-Allylcarbamic Acid tert-Butyl Ester | [Molecular Formula]
C8H15NO2 | [MDL Number]
MFCD00191870 | [MOL File]
78888-18-3.mol | [Molecular Weight]
157.21 |
Chemical Properties | Back Directory | [Melting point ]
36-38 °C(lit.)
| [Boiling point ]
48-50°C/0.3mm | [density ]
0.938 g/mL at 25 °C(lit.)
| [refractive index ]
1.4720 (estimate) | [Fp ]
175 °F
| [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Low Melting Solid | [pka]
12.60±0.46(Predicted) | [color ]
Colorless | [Water Solubility ]
Insoluble in water. Soluble in methanol. | [InChI]
InChI=1S/C8H15NO2/c1-5-6-9-7(10)11-8(2,3)4/h5H,1,6H2,2-4H3,(H,9,10) | [InChIKey]
AWARHXCROCWEAK-UHFFFAOYSA-N | [SMILES]
C(OC(C)(C)C)(=O)NCC=C |
Hazard Information | Back Directory | [Chemical Properties]
white solid crystalline | [Uses]
tert-Butyl N-allylcarbamate is used in the synthesis of isoxazolidines. Synthesis of 5-substituted thiazolidin-2-ones is from the reaction of xanthates and tert-butyl N-allylcarbamates . | [Synthesis]
The synthesis of tert-butyl N-allylcarbamate was carried out as follows:
1. 2.3 mL (30 mmol, 1 eq.) of freshly distilled allylamine was dissolved in 10 mL of dichloromethane (CH2Cl2) in an ice bath (0 °C).
2. 6.54 g (30 mmol, 1 eq.) of di-tert-butyl dicarbonate (Boc2O) dissolved in 20 mL of dichloromethane was slowly added to the above cooled allylamine solution.
3. The reaction mixture was gradually warmed to room temperature with continuous stirring for 4 hours.
4. Upon completion of the reaction, the reaction mixture was diluted with additional dichloromethane and washed sequentially with 5% citric acid solution and brine.
5. The organic layer was separated and dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under vacuum to afford 3.29 g (68% yield) of the target product tert-butyl N-allylcarbamate.
Product characterization data: 1H NMR (500 MHz, CDCl3) δ 1.38 (s, 9H), 3.68 (brs, 2H), 4.53 (brs, 1H), 5.02-5.16 (m, 2H), 5.72-5.84 (m, 1H). | [References]
[1] Tetrahedron Letters, 2007, vol. 48, # 35, p. 6163 - 6166 [2] Angewandte Chemie - International Edition, 2014, vol. 53, # 41, p. 11075 - 11078 [3] Tetrahedron Letters, 1998, vol. 39, # 15, p. 2099 - 2102 [4] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 16, p. 1916 - 1928 [5] Tetrahedron Letters, 2009, vol. 50, # 46, p. 6244 - 6246 |
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