Benzyl vinylcarbamate
- Product Name
- Benzyl vinylcarbamate
- CAS No.
- 84713-20-2
- Chemical Name
- Benzyl vinylcarbamate
- Synonyms
- benzyl vinylcarbamate;N-Cbz-ethenamine;benzyl ethenylcarbamate;BENZYL-N-VINYLCARBAMATE;N-Vinyl-O-benzyl urethane;O-Benzyl-N-vinylcarbamate;benzyl N-ethenylcarbamate;Phenylmethyl ethenylcarbamate;Carbamic acid, N-ethenyl-, phenylmethyl ester
- CBNumber
- CB1679005
- Molecular Formula
- C10H11NO2
- Formula Weight
- 177.2
- MOL File
- 84713-20-2.mol
Benzyl vinylcarbamate Property
- Melting point:
- 43-44°C
- Boiling point:
- 272℃
- Density
- 1.089
- Flash point:
- 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
Safety
- Risk Statements
- 36/37/38
- Safety Statements
- 26-36/37/39
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- B316510
- Product name
- BenzylVinylcarbamate
- Packaging
- 2.5g
- Price
- $305
- Updated
- 2021/12/16
- Product number
- FB141802
- Product name
- Benzyl Vinylcarbamate
- Packaging
- 2g
- Price
- $400
- Updated
- 2021/12/16
- Product number
- 3024AC
- Product name
- Benzylvinylcarbamate
- Packaging
- 2g
- Price
- $590
- Updated
- 2021/12/16
- Product number
- FB141802
- Product name
- Benzyl Vinylcarbamate
- Packaging
- 1g
- Price
- $250
- Updated
- 2021/12/16
- Product number
- FB141802
- Product name
- Benzyl Vinylcarbamate
- Packaging
- 100mg
- Price
- $80
- Updated
- 2021/12/16
Benzyl vinylcarbamate Chemical Properties,Usage,Production
Uses
Benzyl Vinylcarbamate is used as a reagent in the synthesis of CF3- or -?CF2-?substituted tetrahydroquinolines.
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 ℃.
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].
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.
Benzyl vinylcarbamate Preparation Products And Raw materials
Raw materials
Preparation Products
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