O-Benzenedisulfonimide

Base Information

• Chemical Name: O-Benzenedisulfonimide
• CAS No.: 4482-01-3
• Molecular Formula: C6H5NO4S2
• Molecular Weight: 219.242
• Hs Code.: 2934100090
• European Community (EC) Number: 810-929-0
• Nikkaji Number: J934.055F,J3.092.047C
• Mol file: 4482-01-3.mol

Synonyms:O-BENZENEDISULFONIMIDE;4482-01-3;1,2-Benzenedisulfonic Imide;Benzo[d][1,3,2]dithiazole 1,1,3,3-tetraoxide;1lambda6,3lambda6,2-benzodithiazole 1,1,3,3-tetraoxide;1,3,2-Benzodithiazole 1,1,3,3-Tetraoxide;1,2-(Iminobissulfonyl)benzene;SCHEMBL2563736;QRWQFOHBHHIZKG-UHFFFAOYSA-N;MFCD07779379;BS-28682;1,3,2-benzodithiazole 1,1,3,3-tetroxide;B4139;CS-0452616;T70931;Benzo[d][1,3,2]dithiazole1,1,3,3-tetraoxide;2H-benzo[d][1,3,2]dithiazole 1,1,3,3-tetraoxide

Chemical Property of O-Benzenedisulfonimide

Chemical Property:

• Appearance/Colour: Solid
• Melting Point: 192-194°C
• Boiling Point: 456.0±28.0 °C(Predicted)
• PKA: -1.10±0.20(Predicted)
• PSA: 97.07000
• Density: 1.716±0.06 g/cm3(Predicted)
• LogP: 2.15760
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 218.96599999
• Heavy Atom Count: 13
• Complexity: 359

Purity/Quality:

97% ^*data from raw suppliers

1,2-Benzenedisulfonic Imide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)S(=O)(=O)NS2(=O)=O
• General Description: O-BENZENEDISULFONIMIDE, also known as 1,2-benzenedisulfonimide or 1,3,2-benzodithiazole 1,1,3,3-tetraoxide, is a cyclic sulfonimide compound characterized by a benzene ring fused with a disulfonimide moiety. It is a versatile intermediate in organic synthesis, often utilized for its electrophilic properties or as a precursor in the formation of heterocyclic compounds. The structure features two sulfonyl groups adjacent to each other on the benzene ring, contributing to its reactivity and potential applications in catalysis or medicinal chemistry. Its derivatives are of interest due to their unique chemical and biological properties.

Technology Process of O-Benzenedisulfonimide

There total 56 articles about O-Benzenedisulfonimide 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: 95.0%

phenylacetylene (536-74-3) + 2-nitrobenzenediazonium o-benzenedisulfonimide → o-benzenedisulfonimide (4482-01-3) + 1-nitro-2-phenylethynyl-benzene (35010-17-4)

Guidance literature:

With palladium diacetate; dimethyl sulfoxide; at 20 ℃; for 0.0833333h;

DOI:10.1002/ejoc.201301191

Reference yield: 93.0%

tri-n-butylindium (15676-66-1) + 4-toluenediazonium o-benzenedisulfonimide → o-benzenedisulfonimide (4482-01-3) + N-butyl-4-methylaniline (10387-24-3)

Guidance literature:

In tetrahydrofuran; at 20 - 25 ℃;

DOI:10.1002/ejoc.200700931

Reference yield: 92.0%

tri-n-butylindium (15676-66-1) + 4-methoxycarbonylbenzenediazonium o-benzenedisulfonimide → o-benzenedisulfonimide (4482-01-3) + N-(n-butyl)-4-methoxycarbonylaniline (71839-12-8)

Guidance literature:

In tetrahydrofuran; at 20 - 25 ℃;

DOI:10.1002/ejoc.200700931

upstream raw materials:

3-Phenyl-1-propanol

2-(4-Methoxy-benzyl)-benzo[1,3,2]dithiazole 1,1,3,3-tetraoxide

1-Phenylethanol

β-naphthol

Refernces

O-Benzenedisulfonimide as a reusable acid catalyst for an easy, efficient, and green synthesis of tetrahydroisoquinolines and tetrahydro-β-carbolines through Pictet-Spengler reaction

10.1016/j.tetlet.2010.09.149

The study explores the use of o-benzenedisulfonimide as a reusable Br?nsted acid catalyst in the Pictet–Spengler reaction to synthesize tetrahydroisoquinolines and tetrahydro-β-carbolines. These compounds possess various biological activities and are found in numerous natural and synthetic organic compounds. The reaction involves 2-arylethylamine derivatives and aldehydes, with o-benzenedisulfonimide facilitating the cyclization of iminium ions formed from the dehydration reaction of these reactants. The study demonstrates that the catalyst can be easily recovered and reused, offering economic and ecological benefits. The reactions are carried out under mild and green conditions, yielding good target product yields.