| Identification | Back Directory | [Name]
BENZYL-N-VINYLCARBAMATE | [CAS]
84713-20-2 | [Synonyms]
N-Cbz-ethenamine
benzyl vinylcarbamate
BENZYL-N-VINYLCARBAMATE
benzyl ethenylcarbamate
O-Benzyl-N-vinylcarbamate
benzyl N-ethenylcarbamate
N-Vinyl-O-benzyl urethane
Phenylmethyl ethenylcarbamate
Carbamic acid, N-ethenyl-, phenylmethyl ester | [Molecular Formula]
C10H11NO2 | [MDL Number]
MFCD04114067 | [MOL File]
84713-20-2.mol | [Molecular Weight]
177.2 |
| Chemical Properties | Back Directory | [Melting point ]
43-44°C | [Boiling point ]
272℃ | [density ]
1.089 | [Fp ]
118℃ | [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [pka]
11.04±0.46(Predicted) | [color ]
White to Off-White |
| Hazard Information | Back Directory | [Uses]
Benzyl Vinylcarbamate is used as a reagent in the synthesis of CF3- or -?CF2-?substituted tetrahydroquinolines. | [Application]
Benzyl-N-vinyl carbamate (Z-vinylamine; Benzyl vinylcarbamate) is a valuable synthetic intermediate. This compound undergoes alkylation readily on the carbon R to the nitrogen, a property that has been used in the synthesis of a-lactam antibiotics. Z-vinylamine can be readily polymerized into polyvinyl amine derivatives[1].
| [Preparation]
A 1-L flask was equipped with a variable speed pump, a mechanical stirrer, a temperature controller, a 4" (10 cm) column packed with ceramic saddles, a distillation head, a spiral condenser (cooled with water at 10–15 ℃), and a receiver. The flask was charged with toluene (150–200 mL) and phenothiazine (0.5 g) and the solution was heated to 105–110 ℃. The receiver was charged with benzyl alcohol (86 g, 0.8 mol), phenothiazine (0.05 g), and triethylamine (0.1–0.3 g). This mixture was cooled in ice and stirred. A solution of acryloyl azide (1 mol), prepared as described above, was pumped into the distillation flask over a period of 4–5 h, maintaining the pot temperature at 105–110 ℃ with a heating mantle. The vapor temperature varied, depending on the rate of addition of the azide, but was in the range 80–100 ℃. The distillate was passed directly into the benzyl alcohol mixture. After the addition of acryloyl azide, the distillation continued, generating a further 10–20 mL of toluene. The receiver was then removed from the distillation set-up, and its contents were stirred at 0–5 ℃ for 1– 2 h. The product mixture was then allowed to gradually warm to room temperature and was stirred until HPLC analysis indicated complete reaction. The mixture was then concentrated in vacuo to a weight of 200–250 g. The residue was treated with heptane (300–350 mL) and cooled to 15 ℃ with stirring. A few seed crystals of benzyl N-vinyl carbamate 810 were added, and the mixture was stirred for 2–3 h. The product was collected by filtration, washed with heptane, and dried in vacuo. Yield 115–128 g (65–72%); mp 41–44 ℃. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 54, p. 4649, 1989 DOI: 10.1021/jo00280a036 | [References]
[1] Govindan, Cheruthur K. “An Improved Process for the Preparation of Benzyl-N-vinyl Carbamate1.” Organic Process Research Development 6 1 (2001): 74–77.
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