53821-12-8

Basic information

• Product Name: Carbamic acid, (4-nitrophenyl)-, phenylmethyl ester (9CI)
• Synonyms: Carbamic acid, (4-nitrophenyl)-, phenylmethyl ester (9CI);Benzyl N-(4-nitrophenyl)carbamate
• CAS NO: 53821-12-8
• Molecular Formula: C₁₄H₁₂N₂O₄
• Molecular Weight: 272.25608
• Product Categories: N-CBZ
• Mol File: 53821-12-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 155 °C
• Boiling Point: 402.8°Cat760mmHg
• Flash Point: 197.4°C
• Appearance: /
• Density: 1.351g/cm³
• Vapor Pressure: 1.07E-06mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Sparingly), DMSO (Slightly)
• PKA: 12.59±0.70(Predicted)
• CAS DataBase Reference: Carbamic acid, (4-nitrophenyl)-, phenylmethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (4-nitrophenyl)-, phenylmethyl ester (9CI)(53821-12-8)
• EPA Substance Registry System: Carbamic acid, (4-nitrophenyl)-, phenylmethyl ester (9CI)(53821-12-8)

Safety Data

• Hazardous Substances Data: 53821-12-8(Hazardous Substances Data)

Usage

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

Upstream product

• 100-28-7 4-Nitrophenyl isocyanate 
• 100-51-6 benzyl alcohol 
• 100-01-6 4-nitro-aniline 
• 501-53-1 benzyl chloroformate 
• 32455-97-3 Benzyl-N-(2-nitrophenoxy)-carbamat 
• 350-46-9 4-Fluoronitrobenzene 
• 124-38-9 carbon dioxide 
• 100-44-7 benzyl chloride 
• 303158-04-5 (4-nitroso-phenyl)-carbamic acid benzyl ester 
• 62-23-7 4-nitro-benzoic acid 
• 3422-02-4 N-(benzyloxycarbonyl)aniline 
• 3426-71-9 Benzyl N-hydroxycarbamate 
• 104-57-4 benzyl formate 
• 18437-63-3 tert-butyl N-(4-nitrophenyl)carbamate 

Downstream Products

• 100-28-7 4-Nitrophenyl isocyanate 
• 100-51-6 benzyl alcohol 
• 82720-42-1 (4-Amino-phenyl)-carbamic acid benzyl ester 
• 82720-51-2 methyl N-<4-(benzyloxycarboxamido)phenyl>methylphosphonamidate 
• 82720-50-1 2-<4-(benzyloxycarboxamido)phenyl>-2-oxo-1,3,2-dioxaphospholane 
• 82720-49-8 2-<4-(benzyloxycarboxamido)phenyl>-2-oxo-1,3,2-oxazaphosphorinane 
• 82734-34-7 2-<4-(benzyloxycarboxamido)phenyl>-2-oxo-1,3,2-dioxaphosphorinane 
• 82720-29-4 N-Acridin-9-yl-N'-(2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-2-yl)-benzene-1,4-diamine 
• 82720-34-1 C₂₁H₂₀N₃O₂P*ClH 
• 3393-96-2 p-nitrobenzanilide 
• 106-50-3 1,4-phenylenediamine 
• 21260-50-4 N-butyl-N'-(4'-nitrophenyl)urea 

Relevant articles and documents

One stone two birds: Cobalt-catalyzed in situ generation of isocyanates and benzyl alcohols for the synthesis of N-aryl carbamates

An efficient method for the synthesis of N-aryl carbamates from N-Boc-protected amines has been developed. The cobalt-catalyzed in situ generation of isocyanates from N-Boc-protected amines and benzyl alcohols from benzyl formates has been achieved for the first time, which in turn furnished the corresponding benzyl carbamates in moderate to high yields. The reaction was catalyzed by CoI2 with tris-(4-dimethylaminophenyl)-phosphine as the ligand and zinc powder as the reductant. The developed reaction conditions were found to be compatible for aromatic amines with both electron-donating and -withdrawing substituents.

Visible-Light-Mediated Nitration of Protected Anilines

The photocatalytic nitration of protected anilines proceeds with riboflavin tetraacetate as an organic photoredox catalyst. Sodium nitrite serves as the NO2 source in this visible-light-driven room temperature reaction. Various nitroanilines are obtained in moderate to good yields without the addition of acid or stoichiometric oxidation agents. The catalytic cycle is closed by aerial oxygen as the terminal oxidant.

Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates

N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.