5396-86-1

Basic information

• Product Name: prop-2-yn-1-yl (4-chlorophenyl)carbamate
• Synonyms: prop-2-ynyl N-(4-chlorophenyl)carbamate
• CAS NO: 5396-86-1
• Molecular Formula: C₁₀H₈ClNO₂
• Molecular Weight: 209.629
• Mol File: 5396-86-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 260°C at 760 mmHg
• Flash Point: 111°C
• Density: 1.33g/cm³
• Vapor Pressure: 0.0126mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: prop-2-yn-1-yl (4-chlorophenyl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: prop-2-yn-1-yl (4-chlorophenyl)carbamate(5396-86-1)
• EPA Substance Registry System: prop-2-yn-1-yl (4-chlorophenyl)carbamate(5396-86-1)

Safety Data

• Hazardous Substances Data: 5396-86-1(Hazardous Substances Data)

Upstream product

• 104-12-1 p-chlorphenylisocyanate 
• 107-19-7 propargyl alcohol 
• 35718-08-2 propargyl chloroformate 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 135587-19-8 (4-Chloro-phenyl)-carbamic acid 3-bromo-prop-2-ynyl ester 
• 1393790-62-9 C₂₈H₃₀ClF₂N₅O₁₁ 
• 55476-06-7 3-(4-chloro-phenyl)-4-methylene-oxazolidin-2-one 
• 57302-75-7 4-bromo-2-butynyl N-(4-chlorophenyl)carbamate 
• 121192-90-3 4-(diethylamino)-2-butynyl N-(4-chlorophenyl)carbamate 

Relevant articles and documents

Base catalyzed cyclization of N-aryl and N-alkyl-O-propargyl carbamates to 4-alkylidene-2-oxazolidinones

The base catalyzed cyclization of N-aryl and N-alkyl-O-propargyl carbamates is studied in detail. The effect of various bases and solvents on the efficacy of this cyclization reaction is analyzed and a new base-solvent system (LiOH in DMF) for effective cyclization of these carbamates is reported. A number of differentially substituted O-propargyl carbamates were cyclized to the corresponding 2-oxazolidinones under these conditions. The reaction conditions reported here are mild and no side reactions were observed in any of the substrates studied. A propargyl carbonate group was unaffected during the course of the cyclization of the O-propargyl carbamate group. The propargyl carbamates were prepared from the corresponding alkyl or aryl amines and the corresponding propargyl chloroformate, resulting in oxazolidinones diversely substituted at the nitrogen atom. N-Aryl-O-propargyl carbamates cyclized readily to the corresponding oxazolidinones with LiOH in DMF, whereas N-alkyl-O-propargyl carbamates reacted slowly under the same conditions. O-Propargyl carbamates substituted at the 1-position tend to cyclize faster whereas those substituted at 3-position cyclize considerably slower than the unsubstituted carbamates.