(4-Nitrophenyl)methyl (2-mercaptoethyl)carbamate

Base Information

• Chemical Name: (4-Nitrophenyl)methyl (2-mercaptoethyl)carbamate
• CAS No.: 65750-59-6
• Molecular Formula: C10H12N2O4S
• Molecular Weight: 256.282
• European Community (EC) Number: 265-909-9
• DSSTox Substance ID: DTXSID30984283
• Nikkaji Number: J307.479J
• Wikidata: Q82971460
• Mol file: 65750-59-6.mol

Synonyms:65750-59-6;(4-Nitrophenyl)methyl (2-mercaptoethyl)carbamate;(4-nitrophenyl)methyl N-(2-sulfanylethyl)carbamate;EINECS 265-909-9;2-(p-nitrobenzyloxycarbonyl-amino)ethanethiol;SCHEMBL6397529;DTXSID30984283;WZKJVDAVEBGOMU-UHFFFAOYSA-N;Carbamic acid, (2-mercaptoethyl)-, (4-nitrophenyl)methyl ester;N-(4-nitrobenzyloxycarbonyl)cysteamine;2-(4-nitrobenzyloxycarbonyl)aminoethylmercaptan;2-(p-nitrobenzyloxycarbonylamino)ethylmercaptan;A867596;(4-Nitrophenyl)methyl hydrogen (2-sulfanylethyl)carbonimidate

Chemical Property of (4-Nitrophenyl)methyl (2-mercaptoethyl)carbamate

Chemical Property:

• Vapor Pressure: 1.45E-08mmHg at 25°C
• Boiling Point: 457.8°C at 760 mmHg
• Flash Point: 230.7°C
• PSA: 126.44000
• Density: 1.324g/cm³
• LogP: 2.47840
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 256.05177804
• Heavy Atom Count: 17
• Complexity: 262

Purity/Quality:

99% ^*data from raw suppliers

4-Nitrobenzyl(2-Mercaptoethyl)carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1COC(=O)NCCS)[N+](=O)[O-]
• Uses: 4-Nitrobenzyl (2-Mercaptoethyl)carbamate is an intermediate in the synthesis of Thienamycin (T344270). Thienamycin is one of the most potent naturally produced antibiotics known thus far. It has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes.

Technology Process of (4-Nitrophenyl)methyl (2-mercaptoethyl)carbamate

There total 9 articles about (4-Nitrophenyl)methyl (2-mercaptoethyl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

2-mercaptoethylamine hydrochloride (156-57-0) + 4-nitrobenzyl chloroformate (4457-32-3) → 2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) + bis (p-nitrobenzyloxycarbonylaminoethyl)disulfide (67245-90-3) + Thiocarbonic acid O-(4-nitro-benzyl) ester S-[2-(4-nitro-benzyloxycarbonylamino)-ethyl] ester (77381-65-8)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 3.5h;

Reference yield: 81.0%

2-mercaptoethylamine hydrochloride (156-57-0) + C14H10N4O5 → 2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6)

Guidance literature:

With triethylamine; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.56.2974

Reference yield: 66.0%

Cysteamine (60-23-1) + 4-nitrobenzyl chloroformate (4457-32-3) → 2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6)

Guidance literature:

Cysteamine; With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 ℃; for 0.0833333h;

With chloro-trimethyl-silane; In acetonitrile; at 0 ℃; for 0.25h;

4-nitrobenzyl chloroformate; In acetonitrile; at 0 ℃; for 1.5h;

DOI:10.1021/acs.jmedchem.6b00096

upstream raw materials:

Cysteamine

4-nitrobenzyl chloroformate

2-mercaptoethylamine hydrochloride

4-nitrobenzyl chloride

Downstream raw materials:

Trithiocarbonic acid 2-(4-nitro-benzyloxycarbonylamino)-ethyl ester 4-oxo-azetidin-2-yl ester

di-2-(p-nitrobenzyloxycarbonylamino)ethyl trithiocarbonate

C₁₁H₁₁N₂O₄S₃^(1-)*Na⁽¹⁺⁾

2-methyl-1-nitro-2-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>propane

Refernces

• 1、 Shukis, W. F.,Zambito, A. J.,Grabowski, E. J. J.. "CYSTEAMINE N-PROTECTION VIA EQUILIBRATION: PREPARATION OF 4-NITROPHENYLMETHYL 2-MERCAPTOETHYLCARBAMATE FOR USE IN THE SYNTHESIS OF THIENAMYCIN". . p. 613 - 620. Retrieved 2007/10/02.
• 2、 Schmitt, Susan M.,Johnston, David B.R.,Christensen, B.G.. "Thienamycin Total Synthesis. 3. Total Synthesis of (+/-)-Thienamycin and (+/-)-8-Epithienamycin". . p. 1142 - 1148. Retrieved 2007/10/02.