65750-59-6

Basic information

• Product Name: (4-nitrophenyl)methyl (2-mercaptoethyl)carbamate
• Synonyms: (4-nitrophenyl)methyl (2-mercaptoethyl)carbamate
• CAS NO: 65750-59-6
• Molecular Formula: C₁₀H₁₂N₂O₄S
• Molecular Weight: 256.27828
• EINECS: 265-909-9
• Mol File: 65750-59-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 457.8°C at 760 mmHg
• Flash Point: 230.7°C
• Appearance: /
• Density: 1.324g/cm³
• Vapor Pressure: 1.45E-08mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: (4-nitrophenyl)methyl (2-mercaptoethyl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (4-nitrophenyl)methyl (2-mercaptoethyl)carbamate(65750-59-6)
• EPA Substance Registry System: (4-nitrophenyl)methyl (2-mercaptoethyl)carbamate(65750-59-6)

Safety Data

• Hazardous Substances Data: 65750-59-6(Hazardous Substances Data)

Usage

Description

(4-Nitrophenyl)methyl (2-mercaptoethyl)carbamate is an organic compound that serves as a crucial intermediate in the synthesis of Thienamycin (T344270), a potent antibiotic with broad-spectrum activity against various bacteria.

Uses

Used in Pharmaceutical Industry:
(4-Nitrophenyl)methyl (2-mercaptoethyl)carbamate is used as an intermediate in the synthesis of Thienamycin (T344270) for its potent antibiotic properties. Thienamycin is effective against both Gram-positive and Gram-negative bacteria and exhibits resistance to bacterial β-lactamase enzymes, making it a valuable compound in the development of new antibiotics to combat drug-resistant infections.

InChI:InChI=1/C10H12N2O4S/c13-10(11-5-6-17)16-7-8-1-3-9(4-2-8)12(14)15/h1-4,17H,5-7H2,(H,11,13)

Upstream product

• 156-57-0 2-mercaptoethylamine hydrochloride 
• 619-73-8 4-nitrobenzyl chloride 
• 4457-32-3 4-nitrobenzyl chloroformate 
• 60-23-1 Cysteamine 

Downstream Products

• 105780-14-1 2-methyl-1-nitro-2-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>propane 
• 72888-51-8 [2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanylthiocarbonyl]-acetic acid 4-nitro-benzyl ester 
• 126660-27-3 (5S)-2-p-nitrobenzyloxycarbonyl-3-(2-p-nitrobenzyloxycarbonylamino)ethylthio-8-oxo-1-azabicyclo<3.3.0>oct-2-ene 
• 72669-93-3 (2RS,3RS,5RS)-p-nitrobenzyl 3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 72669-93-3 (2RS,3SR,5RS)-p-nitrobenzyl 3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 72669-93-3 (2RS,3RS,5SR)-p-nitrobenzyl 3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 78902-89-3 C₁₁H₁₁N₂O₄S₃^(1-)*Na⁽¹⁺⁾ 
• 77704-92-8 Trithiocarbonic acid 2-(4-nitro-benzyloxycarbonylamino)-ethyl ester 4-oxo-azetidin-2-yl ester 
• 77705-12-5 di-2-(p-nitrobenzyloxycarbonylamino)ethyl trithiocarbonate 
• 1035377-19-5 ethyl (5R,6S)-6-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-3-(2-((4-nitrobenzyloxy)carbonylamino)ethylthio)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 86541-42-6 4-nitrobenzyl (5R,6R)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-3-[2-(4-nitrobenzyloxycarbonylamino)ethylthio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 86489-48-7 4-nitrobenzyl (5R,6S)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-3-[2-(4-nitrobenzyloxycarbonylamino)ethylthio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 90497-57-7 C₁₉H₂₃N₃O₉PS^(1-)*Na⁽¹⁺⁾ 
• 97033-07-3 C₁₈H₃₀N₂O₅SSi₂ 

Relevant articles and documents

Routes of Synthesis of Carbapenems for Optimizing Both the Inactivation of l, d -Transpeptidase LdtMt1 of Mycobacterium tuberculosis and the Stability toward Hydrolysis by β-Lactamase BlaC

Combinations of β-lactams of the carbapenem class, such as meropenem, with clavulanate, a β-lactamase inhibitor, are being evaluated for the treatment of drug-resistant tuberculosis. However, carbapenems approved for human use have never been optimized for inactivation of the unusual β-lactam targets of Mycobacterium tuberculosis or for escaping to hydrolysis by broad-spectrum β-lactamase BlaC. Here, we report three routes of synthesis for modification of the two side chains carried by the β-lactam and the five-membered rings of the carbapenem core. In particular, we show that the azide-alkyne Huisgen cycloaddition reaction catalyzed by copper(I) is fully compatible with the highly unstable β-lactam ring of carbapenems and that the triazole ring generated by this reaction is well tolerated for inactivation of the l,d-transpeptidase LdtMt1 target. Several of our new carbapenems are superior to meropenem both with respect to the efficiency of in vitro inactivation of LdtMt1 and reduced hydrolysis by BlaC.

SYNTHESIS OF MESOIONIC TRIAZOLOPYRIDINE. III. APPLICATIONS OF N-ACYL MESOIONIC TRIAZOLOPYRIDINES AS ACYLATING REAGENTS.

Utility of N-acyl mesoionic triazolopyridines as acylating reagents was investigated concerning with peptide synthesis. Several dipeptides and N-alkoxycarbonyl amino acids were prepared by use of these reagents.

Thienamycin Total Synthesis. 3. Total Synthesis of (+/-)-Thienamycin and (+/-)-8-Epithienamycin

The completion of the total synthesis of (+/-)-8-epithienamycin and (+/-)-thienamycin from azetidinones 3a and 3b using the methodology developed for the synthesis of model compound 4 (see part 2) is described.