S-4-Nitrobenzyl thioacetate

Base Information

• Chemical Name: S-4-Nitrobenzyl thioacetate
• CAS No.: 170640-75-2
• Molecular Formula: C9H9NO3S
• Molecular Weight: 211.241
• DSSTox Substance ID: DTXSID60441415
• Nikkaji Number: J1.971.251F
• Wikidata: Q82258178
• Mol file: 170640-75-2.mol

Synonyms:S-4-Nitrobenzyl thioacetate;170640-75-2;Ethanethioic acid, S-[(4-nitrophenyl)methyl] ester;SCHEMBL8601258;DTXSID60441415;4-Nitro-alpha-toluene thioacetate;S-4-Nitrobenzyl thioacetate, 95%;S-(4-nitrophenylmethyl) thioacetate;Thioacetic acid S-(4-nitrobenzyl) ester;1-{[(4-nitrophenyl)methyl]sulfanyl}ethan-1-one

Chemical Property of S-4-Nitrobenzyl thioacetate

Chemical Property:

• Boiling Point: 347.5±25.0 °C(Predicted)
• PSA: 88.19000
• Density: 1.306±0.06 g/cm3(Predicted)
• LogP: 2.89770
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 211.03031432
• Heavy Atom Count: 14
• Complexity: 219

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)SCC1=CC=C(C=C1)[N+](=O)[O-]

Technology Process of S-4-Nitrobenzyl thioacetate

There total 4 articles about S-4-Nitrobenzyl thioacetate 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: 97.0%

1-bromomethyl-4-nitro-benzene (100-11-8) + potassium thioacetate (10387-40-3) → S-(4-nitrophenylmethyl)thioacetate (170640-75-2)

Guidance literature:

With silica gel; In benzene; at 20 ℃; for 1h;

DOI:10.1081/SCC-120025193

Reference yield: 95.0%

1-bromomethyl-4-nitro-benzene (100-11-8) + tiolacetic acid (507-09-5) → S-(4-nitrophenylmethyl)thioacetate (170640-75-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; toluene; for 4h;

Reference yield: 91.0%

1-bromomethyl-4-nitro-benzene (100-11-8) → S-(4-nitrophenylmethyl)thioacetate (170640-75-2)

Guidance literature:

In acetonitrile; at 20 ℃; for 0.25h;

DOI:10.1007/s13738-012-0093-4

upstream raw materials:

4-nitrobenzyl chloride

tiolacetic acid

1-bromomethyl-4-nitro-benzene

potassium thioacetate

Downstream raw materials:

(p-nitrophenyl)methanethiol

(4-nitrophenyl)methanesulfonyl chloride

1-benzyl-2-(4-nitrobenzyl)disulfane

2',4'-dihydroxy-4-acetophenone

Refernces

• 1、 Gu, Xianfeng,Tan, Jiahui,Wang, Rongchen,Xu, Ge,Zhao, Chunchang,Zhu, Ning,Zhu, Tianli. "Precise imaging of mitochondria in cancer cells by real-time monitoring of nitroreductase activity with a targetable and activatable fluorescent probe". . p. 7761 - 7764. Retrieved 2020.
• 2、 Robins, Morris J.,Peng, Yunshan,Damaraju, Vijaya L.,Mowles, Delores,Barron, Geraldine,Tackaberry, Tracey,Young, James D.,Cass, Carol E.. "Improved syntheses of 5′- S -(2-Aminoethyl)-6- N -(4-nitrobenzyl)- 5′-thioadenosine (SAENTA), analogues, and fluorescent probe conjugates: Analysis of cell-surface human equilibrative nucleoside transporter 1 (hENT1) levels for prediction of the antitumor". supporting information; experimental part. p. 6040 - 6053. Retrieved 2010/11/02.