146328-82-7

Basic information

• Product Name: O-4-fluorophenyl N,N-diethylcarbamate
• Synonyms: O-4-fluorophenyl N,N-diethylcarbamate
• CAS NO: 146328-82-7
• Molecular Weight: 211.236
• Mol File: 146328-82-7.mol

Chemical Properties

• CAS DataBase Reference: O-4-fluorophenyl N,N-diethylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: O-4-fluorophenyl N,N-diethylcarbamate(146328-82-7)
• EPA Substance Registry System: O-4-fluorophenyl N,N-diethylcarbamate(146328-82-7)

Safety Data

• Hazardous Substances Data: 146328-82-7(Hazardous Substances Data)

Upstream product

• 371-41-5 4-Fluorophenol 
• 88-10-8 N,N-diethylcarbamyl chloride 

Downstream Products

• 1417448-24-8 (E)-methyl 3-(2-((diethylcarbamoyl)oxy)-5-fluorophenyl)oct-2-enoate 
• 62433-26-5 (4-chlorophenyl)-(5-fluoro-2-hydroxyphenyl)methanone 
• 1381964-92-6 5-fluoro-2-phenylbenzo[b]furan 
• 21441-24-7 4-fluorophenyl-1H-imidazole 
• 1445899-20-6 4-fluoro-2-hydroxyphenyl diethylcarbamate 
• 1448841-85-7 C₁₇H₂₈FNO₂Si 
• 1448841-95-9 C₂₂H₃₁FN₂O₂Si 
• 146328-83-8 2-Diethylcarbamoyloxy-5-fluoro-benzoic acid 

Relevant articles and documents

N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst

An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is

Experimental and computational study of the 1,5-o → n carbamoyl snieckus-fries-type rearrangement

The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O → N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O → N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized Oarylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.

1,5-O → N Carbamoyl Snieckus-Fries-Type Rearrangement

The reaction of o-lithiated O-aryl N,N-diethylcarbamates with (hetero)aromatic nitriles gives rise to functionalized salicylidene urea derivatives in high yields through a new 1,5-O → N carbamoyl migration. This Snieckus-Fries-type rearrangement nicely complements previously known O → C and O → O related shifts. In addition, when dimethylmalononitrile is used as the electrophilic partner, the carbamoyl shift is preferred over the expected transnitrilation reaction.