84713-20-2

Basic information

• Product Name: BENZYL-N-VINYLCARBAMATE
• Synonyms: BENZYL-N-VINYLCARBAMATE;O-Benzyl-N-vinylcarbamate;benzyl vinylcarbamate;N-Vinyl-O-benzyl urethane;Phenylmethyl ethenylcarbamate
• CAS NO: 84713-20-2
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• Product Categories: organic building block
• Mol File: 84713-20-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 43-44°C
• Boiling Point: 272℃
• Flash Point: 118℃
• Appearance: /
• Density: 1.089
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 11.04±0.46(Predicted)
• CAS DataBase Reference: BENZYL-N-VINYLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL-N-VINYLCARBAMATE(84713-20-2)
• EPA Substance Registry System: BENZYL-N-VINYLCARBAMATE(84713-20-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 84713-20-2(Hazardous Substances Data)

Usage

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 ℃.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 4649, 1989 DOI: 10.1021/jo00280a036

InChI:InChI=1/C10H11NO2/c1-2-11-10(12)13-8-9-6-4-3-5-7-9/h2-7H,1,8H2,(H,11,12)

Upstream product

• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 105-57-7 diethyl acetal 
• 621-84-1 O-benzyl carbamate 
• 50830-56-3 acryloyl azide 
• 100-51-6 benzyl alcohol 
• 501-53-1 benzyl chloroformate 
• 3555-94-0 isocyanatoethene 
• 34325-66-1 vinyl-carbamic acid 

Downstream Products

• 4540-87-8 (2-[[(benzyloxy)carbonyl]amino]ethyl)boronic acid 
• 122313-54-6 methyl 3-<<(benzyloxy)carbonyl>amino>-4,4-dicarbethoxypentanoate 
• 122313-53-5 methyl 3-methoxy-3-<<(benzyloxy)carbonyl>amino>propionate 
• 908810-06-0 methyl 3-<<(benzyloxy)carbonyl>amino>-4-carbobenzoxy-5-oxohexanoate 
• 122313-52-4 benzyl N-(1-methoxyethyl)carbamate 
• 135740-99-7 methyl 3-<(benzyloxycarbonyl)amino>-2-(methoxycarbonyl)-5-oxo-6-hepteneoate 
• 135741-03-6 methyl 3-<(benzyloxycarbonyl)amino>-2-(methoxycarbonyl)-5-oxo-5-phenylpentanoate 
• 135741-05-8 methyl 3-<(benzyloxycarbonyl)amino>-2-(methoxycarbonyl)-5-oxo-5-(p-methoxyphenyl)pentanoate 
• 135741-07-0 methyl 3-<(benzyloxycarbonyl)amino>-5-(2-furanyl)-2-(methoxycarbonyl)-5-oxopentanoate 
• 135741-09-2 methyl 3-<(benzyloxycarbonyl)amino>-2-(methoxycarbonyl)-5-oxo-6-octynoate 
• 135741-01-4 methyl 3-<(benzyloxycarbonyl)amino>-2-(methoxycarbonyl)-7-methyl-5-oxo-6-octenoate 
• 135741-04-7 methyl 3-<(benzyloxycarbonyl)amino>-2-(methoxycarbonyl)-5-oxo-5-(p-tolyl)pentanoate 
• 135741-06-9 methyl 3-<(benzyloxycarbonyl)amino>-2-(methoxycarbonyl)-5-oxo-5-(p-chlorophenyl)pentanoate 
• 135741-00-3 (E)-methyl 3-<(benzyloxycarbonyl)amino>-2-(methoxycarbonyl)-5-oxo-7-phenyl-6-hepteneoate 

Relevant articles and documents

An improved process for the preparation of benzyl-N-vinyl carbamate

An improved method that can be easily scaled up has been developed for the preparation of benzyl-N-vinyl carbamate. In this method vinyl isocyanate formed by the Curtius rearrangement of acryloyl azide is codistilled with a solvent such as toluene into benzyl alcohol containing a catalyst and inhibitor. The product thus obtained can be purified by crystallization, avoiding purification by high-vacuum distillation or chromatography. Potential safety issues associated with the process are discussed.

INHIBITING DEUBIQUITINASE USP25 AND USP28

The present disclosure relates to modulators, such as inhibitors, of at least one pathway chosen from USP28 and USP25, pharmaceutical compositions comprising the inhibitors, and methods of using the inhibitors. The modulators, such as inhibitors, of at least one pathway chosen from USP28 and USP25 can be useful in the treatment of cancers, among other ailments. The present disclosure provides compounds of Formula (I).

A process for the preparation and synthetic ChondriamideA and ChondriamideC method (by machine translation)

The invention provides a process for the preparation of synthetic Chondriamide A and Chondriamide C and method, wherein the invention provides a process for the preparation, including: formula (I) compounds of structure, palladium catalyst, phosphorus ligand, alkali and organic solvent at room temperature the illumination reaction, formula (II) structure obtained olefin; wherein through the selection of a particular phosphorus ligand; make the method of the invention can be under the photocatalysis, room temperature to realize high-efficient catalytic conversion, and the mild reaction conditions, simple operation, in line with the development of green environment-friendly chemical requirements, and the range of choice of substrate and functional group compatibility has more universal, and has outstanding chemical selectivity; and the method can be successfully applied to complex molecular introducing carbon-carbon double bond to the programme, to optimize a part of the drug molecular synthesis strategy, improve the synthesis efficiency, reduce the cost, with industrial synthetic value and prospects. (by machine translation)