4-Nitrobenzenesulfonyl chloride

Base Information

• Chemical Name: 4-Nitrobenzenesulfonyl chloride
• CAS No.: 98-74-8
• Deprecated CAS: 1623050-71-4
• Molecular Formula: C6H4ClNO4S
• Molecular Weight: 221.621
• Hs Code.: 29049085
• European Community (EC) Number: 202-697-9
• NSC Number: 13065,9572
• UNII: ZU5JD6BHB3
• DSSTox Substance ID: DTXSID4059178
• Nikkaji Number: J145.068I
• Wikidata: Q72494331
• ChEMBL ID: CHEMBL4753649
• Mol file: 98-74-8.mol

Synonyms:4-nitrobenzenesulfonyl chloride;NBSO2Cl;p-nitrobenzenesulfonyl chloride

Chemical Property of 4-Nitrobenzenesulfonyl chloride

Chemical Property:

• Appearance/Colour: yellow to brown powder
• Vapor Pressure: 9.33E-05mmHg at 25°C
• Melting Point: 75 °C
• Refractive Index: 1.588
• Boiling Point: 349.7 °C at 760 mmHg
• Flash Point: 165.3 °C
• PSA: 88.34000
• Density: 1.606 g/cm³
• LogP: 3.12630
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Solubility.: soluble in Toluene
• Water Solubility.: Insoluble
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 220.9549565
• Heavy Atom Count: 13
• Complexity: 283

Purity/Quality:

99%, ^*data from raw suppliers

4-Nitrobenzenesulfonyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-52/53
• Safety Statements: 26-36/37/39-45-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])S(=O)(=O)Cl
• Uses: 4-Nitrobenzenesulfonyl Chloride is used in the preparation of N-Nosyl-α-amino acid for peptide synthesis. 4-Nitrobenzenesulfonyl chloride is used as an intermediate for the synthesis of pharmaceuticals like foscmprenavir, darunavir and amprenavir. It is involved in the preparation of N-nosyl-alpha-amino acid for peptide synthesis. It is also used for stereoselective α-glucosylation of partially protected carbohydrates in association with silver tri-fluoromethanesulfonate, N,N-dimethylacetamide and triethylamine. It is widely used for the synthesis of hydroxylamines of sulfadiazine, sulfamethoxazole and [Cu(bipy)2Cl](nbs) (1) (bipy = 2,2'-bipyridine, nbs = 4-nitrobenzenesulfonate). 4-Nitrobenzenesulfonyl chloride was used in the synthesis of [Cu(bipy)2Cl](nbs) (1) (bipy = 2,2′-bipyridine, nbs = 4-nitrobenzenesulfonate)hydroxylamines of sulfadiazine and sulfamethoxazolesolution phase peptide using N-nosyl-α-amino acids.

Technology Process of 4-Nitrobenzenesulfonyl chloride

There total 25 articles about 4-Nitrobenzenesulfonyl chloride 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: 96.0%

di(p-nitrophenyl) disulfide (100-32-3) → 4-Nitrobenzenesulfonyl chloride (98-74-8)

Guidance literature:

With dihydrogen peroxide; zirconium(IV) chloride; In water; acetonitrile; at 25 ℃; for 0.0166667h;

DOI:10.1055/s-0029-1217989

Reference yield: 95.6%

1-acetylsulfanyl-4-nitro-benzene (15119-62-7) → 4-Nitrobenzenesulfonyl chloride (98-74-8)

Guidance literature:

With hydrogenchloride; N-chloro-succinimide; In acetonitrile; at 10 ℃;

DOI:10.1055/s-2006-950353

Reference yield: 95.0%

1-methylthio-4-nitro-benzene (701-57-5) → 4-Nitrobenzenesulfonyl chloride (98-74-8)

Guidance literature:

With sulfuryl dichloride; sodium sulfate; In water; chlorobenzene;

upstream raw materials:

4-nitrobenzenesulfenyl chloride

di(p-nitrophenyl) disulfide

4-nitrobenzenediazonium chloride

para-nitrobenzenethiol

Downstream raw materials:

4-nitro-N-5-methyl-thiazol-2-yl-benzenesulfonamide

4-amino-N-methyl-N-(pyrimidin-2-yl)benzene-1-sulfonamide

2-amino-5-cyanothiazole

4-nitro-N-(6-methylsulfanyl-pyridazin-3-yl)-benzenesulfonamide

Refernces

• 1、 Antonietti, Markus,Guldi, Dirk M.,Markushyna, Yevheniia,Savateev, Aleksandr,Schü?lbauer, Christoph M.,Ullrich, Tobias. "Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst". supporting information. p. 20543 - 20550. Retrieved 2021/08/12.
• 2、 Májek, Michal,Neumeier, Michael,Jacobi von Wangelin, Axel. "Aromatic Chlorosulfonylation by Photoredox Catalysis". . p. 151 - 155. Retrieved 2017/01/17.