4-Nitrobenzyl triflate

Base Information

• Chemical Name: 4-Nitrobenzyl triflate
• CAS No.: 114533-06-1
• Molecular Formula: C8H6F3NO5S
• Molecular Weight: 285.201
• DSSTox Substance ID: DTXSID60556013
• Wikidata: Q82437477
• Mol file: 114533-06-1.mol

Synonyms:4-Nitrobenzyl triflate;114533-06-1;(4-Nitrophenyl)methyl trifluoromethanesulfonate;SCHEMBL5912986;DTXSID60556013;DFMFSSOQMCTCGK-UHFFFAOYSA-N

Chemical Property of 4-Nitrobenzyl triflate

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 284.99187795
• Heavy Atom Count: 18
• Complexity: 388

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1COS(=O)(=O)C(F)(F)F)[N+](=O)[O-]

Technology Process of 4-Nitrobenzyl triflate

There total 6 articles about 4-Nitrobenzyl triflate 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: 84.0%

silver trifluoromethanesulfonate (2923-28-6) + 1-bromomethyl-4-nitro-benzene (100-11-8) → (4-nitrophenyl)methyl trifluoromethanesulfonate (114533-06-1)

Guidance literature:

With 4-pentynyl-1-tosylate; In tetrachloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ja5124368

Reference yield:

4-nitrobenzyl chloride (619-73-8) + trifluoromethylsulfonic anhydride (358-23-6) → (4-nitrophenyl)methyl trifluoromethanesulfonate (114533-06-1)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; In dichloromethane; at 0 - 23 ℃; Inert atmosphere;

DOI:10.1002/anie.200902248

Reference yield:

p-nitrobenzylamine (7409-30-5) → (4-nitrophenyl)methyl trifluoromethanesulfonate (114533-06-1)

Guidance literature:

Multi-step reaction with 3 steps

2: 1) NaOH, 2) N₂O₄, Na₂CO₃ / 2.) CH₂Cl₂, -10 deg C

3: 2,6-di-tert-butyl-4-methylpyridine / CDCl₃

With sodium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; dinitrogen tetraoxide; sodium carbonate; In chloroform-d1;

DOI:10.1021/ja00219a082

upstream raw materials:

C₈H₆F₃N₃O₅S

silver trifluoromethanesulfonate

1-bromomethyl-4-nitro-benzene

p-nitrobenzylamine

Downstream raw materials:

N-(t-Butoxycarbonyl)-3-(4-nitrobenzyl)-L-histidine methyl ester

(E)-3-(4-nitrobenzyloxy)-3,7,11-trimethyldodeca-6,10-dien-1-yne

3-(4-nitrobenzyloxy)-3,7-dimethyloct-6-en-1-yne

(Z)-3-(4-nitrobenzyloxy)-3,7,11-trimethyldodeca-6,10-dien-1-yne

Refernces

• 1、 Jimenez-Nunez, Eloisa,Raducan, Mihai,Lauterbach, Thorsten,Malawi, Kian,Solorio, Cesar R.,Echavarren, Antonio M.. "Evolution of propargyl ethers into allylgold cations in the cyclization of enynes". supporting information; experimental part. p. 6152 - 6155. Retrieved 2009/12/09.
• 2、 White, Emil H.,DePinto, Jeffrey T.,Polito, Albert J.,Bauer, Ines,Roswell, David F.. "The Preparation of Carbonium Ions and other High-energy Alkylating Agents under Mild Conditions". . p. 3708 - 3709. Retrieved 2007/10/02.