4-Iodobenzenesulfonyl chloride

Base Information

• Chemical Name: 4-Iodobenzenesulfonyl chloride
• CAS No.: 98-61-3
• Molecular Formula: C6H4ClIO2S
• Molecular Weight: 302.52
• Hs Code.: 29049020
• European Community (EC) Number: 202-686-9
• NSC Number: 77079
• UNII: MVL274EZOG
• DSSTox Substance ID: DTXSID9059175
• Nikkaji Number: J4.955G
• Wikidata: Q27284258
• Mol file: 98-61-3.mol

Synonyms:4-iodophenylsulfonyl chloride;p-iodophenylsulfonyl chloride;pipsyl chloride

Chemical Property of 4-Iodobenzenesulfonyl chloride

Chemical Property:

• Appearance/Colour: white to beige or orange crystals
• Vapor Pressure: 0.000647mmHg at 25°C
• Melting Point: 80-82 °C(lit.)
• Refractive Index: 1.639
• Boiling Point: 319.1 °C at 760 mmHg
• Flash Point: 146.8 °C
• PSA: 42.52000
• Density: 2.041 g/cm³
• LogP: 3.29950
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: ethanol: soluble100mg/mL, clear to slightly hazy, colorless to y
• Water Solubility.: Reacts with water.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 301.86653
• Heavy Atom Count: 11
• Complexity: 213

Purity/Quality:

99% ^*data from raw suppliers

4-Iodobenzenesulfonyl Chloride >93.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1S(=O)(=O)Cl)I
• Uses: It is used as intermediate in organic syntheses & in medicine.

Technology Process of 4-Iodobenzenesulfonyl chloride

There total 11 articles about 4-Iodobenzenesulfonyl 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: 87.0%

4-iodobenzenediazonium tetrafluoroborate (1514-50-7) → p-Iodobenzenesulfonyl chloride (98-61-3)

Guidance literature:

With thionyl chloride; tris(bipyridine)ruthenium(II) dichloride hexahydrate; In water; acetonitrile; at 20 ℃; for 20h; Sealed tube; Irradiation;

DOI:10.1002/cssc.201601293

Reference yield: 64.0%

4-iodophenylboronic acid (5122-99-6) → p-Iodobenzenesulfonyl chloride (98-61-3)

Guidance literature:

With phenylchlorosulfate; C₄₃H₄₃NO₃PPdS; sodium carbonate; In acetone; at 55 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1021/ja405949a

Reference yield:

4-iodobenzenesulfonic acid (13035-63-7) → p-Iodobenzenesulfonyl chloride (98-61-3)

Guidance literature:

With phosphorus pentachloride;

DOI:10.1021/ja01169a064

upstream raw materials:

iodobenzene

4-iodothioanisole

4-iodobenzenesulfonic acid

ethyl-(4-iodo-phenyl)-sulfide

Downstream raw materials:

4-iodobenzenesulfonic acid methyl ester

N-(4-iodo-benzenesulfonyl)-leucine

N-(4-iodo-benzenesulfonyl)-aspartic acid

1,2-bis(4-Iodophenyl)disulfane

Refernces

Glycosidations of 2-deoxy glycosyl dithiophosphates using a tagged iodine(iii)-promoter for simple purification

10.1039/b718642h

The research focuses on the development of a novel purification strategy for iodine(III)-promoted glycosidations of 2-deoxy diethyldithiophosphate glycosides using a tagged iodine(III)-promoter. The purpose of this study was to address the challenges associated with the removal of by-products, such as iodobenzene, which are common in hypervalent iodine chemistry and can be cumbersome to remove chromatographically. The researchers introduced a concept based on a sulfonate ester tag that acts as a dormant ion exchange group, allowing for the liberation and removal of the sulfonate anion via an SN2-step and subsequent anion exchange resin capture. The tagged iodine(III) reagents were prepared from commercially available p-iodo-benzenesulfonyl chloride (pipsyl chloride) and were used to activate glycosyl donors in the presence of various glycosyl acceptors. The study concluded that this method, combined with a scavenging protocol, is a powerful glycosidation approach for diethyldithiophosphates and has general applicability for purification protocols of reagents and catalysts. Key chemicals used in the process include p-iodo-benzenesulfonyl chloride, i-butyl sulfonate, bis(acetoxy)iodoarene, iodosylbenzene, and the Zefirov reagent, as well as various glycosyl donors and acceptors such as diethyldithiophosphates and decarestrictines.