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| | tert-Butyl N-allylcarbamate Basic information |
| Product Name: | tert-Butyl N-allylcarbamate | | Synonyms: | ALLYL-CARBAMIC ACID TERT-BUTYL ESTER;N-ALLYL-T-BUTYLCARBAMATE;3-(tert-Butoxycarbonylamino)-1-propene;N-(tert-Butyloxycarbonyl)-2-propene-1-amine;N-Allylcarbamic acid tert-butyl ester;tert-Butoxycarbonylallylamine;tert-Butyl N-Allylcarbamate;Carbamic acid, 2-propenyl-, 1,1-dimethylethyl ester (9CI) | | CAS: | 78888-18-3 | | MF: | C8H15NO2 | | MW: | 157.21 | | EINECS: | | | Product Categories: | N-BOC;Allyl Monomers;Monomers;Polymer Science | | Mol File: | 78888-18-3.mol |  |
| | tert-Butyl N-allylcarbamate Chemical Properties |
| 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 | | pka | 12.60±0.46(Predicted) | | form | Low Melting Solid | | 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 Codes | Xi,Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 22-26-36/37/39 | | RIDADR | UN 1325 4.1/PG 2 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29241990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral |
| | tert-Butyl N-allylcarbamate Usage And Synthesis |
| 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 |
| | tert-Butyl N-allylcarbamate Preparation Products And Raw materials |
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