4-Nitrobenzenesulfonyl fluoride

Base Information

• Chemical Name: 4-Nitrobenzenesulfonyl fluoride
• CAS No.: 349-96-2
• Molecular Formula: C6H4FNO4S
• Molecular Weight: 205.166
• Hs Code.: 29049090
• European Community (EC) Number: 631-547-9
• DSSTox Substance ID: DTXSID00188458
• Nikkaji Number: J208.801K
• Wikidata: Q83060264
• Mol file: 349-96-2.mol

Synonyms:4-nitrobenzenesulfonyl fluoride;para-nitrobenzenesulfonyl fluoride;PNBSF

Chemical Property of 4-Nitrobenzenesulfonyl fluoride

Chemical Property:

• Vapor Pressure: 0.00151mmHg at 25°C
• Melting Point: 76-80 °C
• Refractive Index: 1.544
• Boiling Point: 305.1 °C at 760 mmHg
• Flash Point: 138.3 °C
• PSA: 88.34000
• Density: 1.554 g/cm³
• LogP: 2.85700
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 204.98450694
• Heavy Atom Count: 13
• Complexity: 283

Purity/Quality:

99% ^*data from raw suppliers

4-Nitrobenzenesulfonyl Fluoride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-26-27

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])S(=O)(=O)F
• Uses: 4-Nitrobenzenesulfonyl Fluoride is a protein modifying agent shown to be specific for tyrosine. Sulfonyl fluoride motif can be used as a connector for the assembly of -SO2- linked small molecules with proteins or nucleic acids. This new click chemistry approach through sulfates is a complimentary approach to using amides and phosphate groups as linkers.

Technology Process of 4-Nitrobenzenesulfonyl fluoride

There total 12 articles about 4-Nitrobenzenesulfonyl fluoride 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%

→ 4-nitrobenzenesulfonyl fluoride (349-96-2)

Guidance literature:

With potassium hydrogen difluoride; In water; acetonitrile; at 20 ℃; for 3h;

Reference yield: 96.0%

4-Nitrobenzenesulfonyl chloride (98-74-8) → 4-nitrobenzenesulfonyl fluoride (349-96-2)

Guidance literature:

With potassium fluoride; 18-crown-6 ether; In water; toluene; at 55 ℃; for 8h; Large scale;

DOI:10.1021/acs.oprd.0c00080

Reference yield: 75.0%

3,3,7,7-tetrakis(difluoramino)octahydro-1,5-bis(4-nitrobenzenesulfonyl)-1,5-diazocine → 4-nitrobenzenesulfonyl fluoride (349-96-2) + 3,3,7,7-tetrakis(difluoroamino)octahydro-1,5-dinitro-1,5-diazocine

Guidance literature:

3,3,7,7-tetrakis(difluoramino)octahydro-1,5-bis(4-nitrobenzenesulfonyl)-1,5-diazocine; With trifluorormethanesulfonic acid; at 20 - 40 ℃; for 328h;

With nitric acid; at 0 - 20 ℃; for 1.08333h;

With sodium carbonate; In water; at 0 ℃; pH=5; Product distribution / selectivity;

upstream raw materials:

4-Nitrobenzenesulfonyl chloride

4-nitrobenzenesulfenyl chloride

dichloromethane

di(p-nitrophenyl) disulfide

Downstream raw materials:

4-aminobenzenesulfonyl fluoride

p-nitrobenzenesulfonamide

C₁₀H₇F₉N₂O₄S₂

C₁₆H₁₄F₈N₄O₈S₄

Refernces

• 1、 Xu, Shuheng,Cui, Sunliang. "SuFExable Isocyanides for Ugi Reaction: Synthesis of Sulfonyl Fluoro Peptides". supporting information. p. 5197 - 5202. Retrieved 2021/07/20.
• 2、 Louvel, Dan,Chelagha, Aida,Rouillon, Jean,Payard, Pierre-Adrien,Khrouz, Lhoussain,Monnereau, Cyrille,Tlili, Anis. "Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism". supporting information. p. 8704 - 8708. Retrieved 2021/05/17.