ChemicalBook > CAS DataBase List > Benzyl vinylcarbamate

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
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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
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Safety

Risk Statements 
36/37/38
Safety Statements 
26-36/37/39
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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.

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N-Bromosuccinimide Price

TRC
Product number
B316510
Product name
BenzylVinylcarbamate
Packaging
2.5g
Price
$305
Updated
2021/12/16
Biosynth Carbosynth
Product number
FB141802
Product name
Benzyl Vinylcarbamate
Packaging
2g
Price
$400
Updated
2021/12/16
AK Scientific
Product number
3024AC
Product name
Benzylvinylcarbamate
Packaging
2g
Price
$590
Updated
2021/12/16
Biosynth Carbosynth
Product number
FB141802
Product name
Benzyl Vinylcarbamate
Packaging
1g
Price
$250
Updated
2021/12/16
Biosynth Carbosynth
Product number
FB141802
Product name
Benzyl Vinylcarbamate
Packaging
100mg
Price
$80
Updated
2021/12/16
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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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