124068-97-9

Basic information

• Product Name: 4-NITRO-PHENYL-N-BENZYLCARBAMATE
• Synonyms: 4-Nitrophenyl N-Benzylcarbamate;4-Nitrophenyl benzylcarbamate
• CAS NO: 124068-97-9
• Molecular Formula: C₁₄H₁₂N₂O₄
• Molecular Weight: 272.26
• Mol File: 124068-97-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 130.0 to 134.0 °C
• Boiling Point: 436.1°Cat760mmHg
• Flash Point: 217.5°C
• Appearance: /
• Density: 1.306g/cm³
• Vapor Pressure: 8.32E-08mmHg at 25°C
• Refractive Index: 1.609
• PKA: 10.54±0.46(Predicted)
• BRN: 4261736
• CAS DataBase Reference: 4-NITRO-PHENYL-N-BENZYLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITRO-PHENYL-N-BENZYLCARBAMATE(124068-97-9)
• EPA Substance Registry System: 4-NITRO-PHENYL-N-BENZYLCARBAMATE(124068-97-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 124068-97-9(Hazardous Substances Data)

Usage

Description

4-NITRO-PHENYL-N-BENZYLCARBAMATE is an organic compound that serves as a versatile reactant in the synthesis of various chemical compounds and pharmaceutical agents. It is characterized by its ability to form carbamate linkages, which are essential in the development of drugs and other chemical entities.

Uses

Used in Pharmaceutical Industry:
4-NITRO-PHENYL-N-BENZYLCARBAMATE is used as a reactant for the preparation of radiofluorinated quinoxalinedione derivatives, which are potential ligands of the AMPA receptor. These ligands are important for studying the function and modulation of AMPA receptors, which play a crucial role in neurological processes and are implicated in various neurological disorders.
Used in Peptide Synthesis:
In the field of peptide synthesis, 4-NITRO-PHENYL-N-BENZYLCARBAMATE is utilized as a reactant for the preparation of mono-substituted urea side chains in solid phase peptide synthesis. This application is significant for the development of novel peptides with specific biological activities and potential therapeutic applications.
Used in Organic Synthesis:
4-NITRO-PHENYL-N-BENZYLCARBAMATE is also used as a reactant for the synthesis of 4-substituted-1,2,4-triazolidine-3,5-diones. These compounds are of interest in organic chemistry due to their unique structural features and potential applications in various chemical transformations.
Used in Enzyme Inhibition Studies:
Furthermore, 4-NITRO-PHENYL-N-BENZYLCARBAMATE is employed in the preparation of aryl carbamates, which serve as probes for understanding the inhibition mechanism of cholesterol esterase. This enzyme plays a key role in lipid metabolism, and its inhibition can have implications in the treatment of various metabolic disorders and diseases.

InChI:InChI=1/C14H12N2O4/c17-14(15-10-11-4-2-1-3-5-11)20-13-8-6-12(7-9-13)16(18)19/h1-9H,10H2,(H,15,17)

Upstream product

• 7693-46-1 4-Nitrophenyl chloroformate 
• 100-46-9 benzylamine 
• 3287-99-8 benzylamine hydrochloride 
• 100-02-7 4-nitro-phenol 
• 3173-56-6 benzyl isothiocyanate 
• 50780-50-2 4-chloromethoxycarbonyloxy-1-nitrobenzene 

Downstream Products

• 3173-56-6 benzyl isothiocyanate 
• 57965-06-7 ethyl 2-(benzylcarbamoyl)hydrazine-1-carboxylate 
• 100-02-7 4-nitro-phenol 
• 16312-86-0 4-benzyl-1,2,4-triazolidine-3,5-dione 
• 104096-61-9 N-benzyl-N'-(3-hydroxy-propyl)-urea 
• 335459-64-8 1-benzyl-3-(cyclohexylmethyl)urea 

Relevant articles and documents

Discovery of Biased Mu-Opioid Receptor Agonists for the Treatment of Pain

G protein-biased mu-opioid receptor (MOR) agonists have been developed as promising new potent analgesic drugs with fewer adverse side effects than standard MOR agonists. PZM21 represents a unique chemotype unrelated to known opioids, which makes it a desirable lead for modification to find analgesics with new chemical entities. In the present study, we synthesized and tested novel PZM21 derivatives as potent biased MOR agonists by introducing a benzodioxolane group to replace the hydroxybenzene of PZM21. The new compounds displayed more potent analgesic activities in vivo and greater bias toward G protein signaling in vitro than did PZM21. These results suggest that the benzodioxolane group is essential for the maintenance of bias. Compounds 7 i ((S)-1-(3-(benzo[d][1,3]dioxol-4-yl)-2-(dimethylamino)propyl)-3-phenethylurea) and 7 j ((S)-1-(3-(benzo[d][1,3]dioxol-4-yl)-2-(dimethylamino)propyl)-3-benzylurea) could serve as new leads for further modifications to find novel biased MOR agonists with greater G protein signaling potency and less β-arrestin-2 recruitment.

A simple and efficient biphasic method for the preparation of 4-nitrophenyl N-methyl- and N-alkylcarbamates

Treatment of 4-nitrophenyl chloroformate with alkylammonium hydrochloride salts and solid anhydrous Na2CO3 in either CH2Cl2 or CH3CN gave 4-nitrophenyl N-methylcarbamate and other N-alkylcarbamate ana

Biased agonist and medical application thereof

The invention relates to compounds shown in structural formulas I and II, stereoisomers or pharmaceutically acceptable salts thereof, and a pharmaceutical composition containing the compounds, the stereoisomers or the pharmaceutically acceptable salts thereof as active ingredients, and uses of the compound, the stereoisomer thereof or the pharmaceutically acceptable salt thereof in preparation ofanalgesic drugs.

Reactive Oxygen Species-Triggered Tunable Hydrogen Sulfide Release

A series of carbamothioates with tunable release of H2S after activation by reactive oxygen species are reported. The half-lives of H2S release could be tuned from 24 to 203 min by varying the basicity of the amine.