Tosyl isocyanate

Base Information

• Chemical Name: Tosyl isocyanate
• CAS No.: 4083-64-1
• Deprecated CAS: 102086-99-7
• Molecular Formula: C8H7NO3S
• Molecular Weight: 197.214
• Hs Code.: 29309090
• European Community (EC) Number: 223-810-8
• UNII: H9004FJX6V
• DSSTox Substance ID: DTXSID1027558
• Nikkaji Number: J195C
• Wikidata: Q27279783
• ChEMBL ID: CHEMBL1879981
• Mol file: 4083-64-1.mol

Synonyms:Tosyl isocyanate;4083-64-1;p-Toluenesulfonyl isocyanate;4-Methylbenzenesulfonyl isocyanate;p-Toluenesulphonyl isocyanate;Benzenesulfonyl isocyanate, 4-methyl-;4-methyl-N-(oxomethylidene)benzenesulfonamide;p-Tolylsulfonyl isocyanate;p-toluenesulfonylisocyanate;PtSi;p-Toluenesulfonic acid, anhydride with isocyanic acid;EINECS 223-810-8;p-Tosyl isocyanate;p-TOLUENE SULFONYL ISOCYANATE;4-methylbenzene-1-sulfonyl isocyanate;4-Toluenesulfonyl isocyanate;UNII-H9004FJX6V;H9004FJX6V;DTXSID1027558;p-Methylphenylsulfonyl isocyanate;4-Methylphenylsulfonyl isocyanate;4-Methylbenzene-1-sulphonyl isocyanate;EC 223-810-8;C8H7NO3S;DTXCID407558;Tosylisocyanate;CAS-4083-64-1;TosNCO;(4-methylphenyl)sulfonylisocyanate;TsNCO;p-tolylsulfonyl-isocyanate;Sulfone, isocyanato tolyl;DSSTox_CID_7558;p-toluenesulphonylisocyanate;p-Toluensulfonyl isocyanate;p-toluene sulfonylisocyanate;DSSTox_RID_78504;DSSTox_GSID_27558;p-toluene-sulfonyl isocyanate;para-toluenesulfonylisocyanate;SCHEMBL22302;4-Isocyanatosulphonyltoluene,;p-toluene sulphonyl isocyanate;para-toluene sulfonylisocyanate;4-toluene-sulphonyl isocyanate;CHEMBL1879981;VLJQDHDVZJXNQL-UHFFFAOYSA-;4-Methylphenylsulphonyl isocyanate;4-methyl-benzenesulfonyl isocyanate;p-Toluenesulfonyl isocyanate, 96%;AMY23367;Tox21_201698;Tox21_303136;BBL011351;MFCD00002030;STL146441;AKOS000119298;NCGC00164078-01;NCGC00164078-02;NCGC00257105-01;NCGC00259247-01;P-METHYLBENZENESULFONYL ISOCYANATE;LS-32159;PS-10276;FT-0635118;T0998;4-methyl-N-(oxo-methylene)-benzenesulfonamide;EN300-19005;E76074;A937481;J-524974;Q27279783;F0001-1154;ISOCYANIC ACID, ANHYDRIDE WITH P-TOLUENESULFONIC ACID;p-Toluenesulfonyl isocyanate, for HPLC derivatization, >=98.0% (HPLC)

Chemical Property of Tosyl isocyanate

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 1 mm Hg ( 100 °C)
• Melting Point: 5°C
• Refractive Index: 1.5340
• Boiling Point: 288.8 °C at 760 mmHg
• Flash Point: 128.5 °C
• PSA: 71.95000
• Density: 1.27 g/cm³
• LogP: 2.10030
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: reacts
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 197.01466426
• Heavy Atom Count: 13
• Complexity: 303

Purity/Quality:

98% ^*data from raw suppliers

p-Toluenesulfonyl isocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 14-36/37/38-42
• Safety Statements: 26-28-30-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N=C=O
• Uses: p-Toluenesulfonyl isocyanate is a reagent used to prepare acetylated syn-1,2-diols,1 oxazolidin-2-ones,2 2,3-diamino acids,3 and N-tosylcarbonamides.4 It is a reagent used to prepare acetylated syn-1,2-diols,oxazolidin-2-ones, 2,3-diamino acids, and N-tosylcarbonamides. -Toluenesulfonyl isocyanate has been used as derivatization reagent in determination of 3-α-hydroxy tibolone in human plasma by LC-MS/MS. It is also employed in the derivatization reagent in simultaneous quantitative analysis of diethylene glycol and propylene glycol in pharmaceutical products by HPLC and as reagent in the preparation of acetylated syn-1,2-diols, oxazolidin-2-ones, 2,3-diamino acids and N-tosylcarbonamides.

Technology Process of Tosyl isocyanate

There total 16 articles about Tosyl isocyanate 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%

p-toluenesulfonylcarbamyl fluoride → Tosyl isocyanate (4083-64-1)

Guidance literature:

In toluene; at 140 ℃; for 2h; Glovebox;

DOI:10.1016/j.jfluchem.2015.05.007

Reference yield: 75.0%

4-toluenesulfonyl azide (941-55-9) + carbon monoxide (201230-82-2) → Tosyl isocyanate (4083-64-1) + toluene-4-sulfonamide (70-55-3)

Guidance literature:

With palladium diacetate; In acetonitrile; at 40 ℃; for 4h; Schlenk technique;

DOI:10.1039/d0cc04565a

Reference yield: 60.0%

carbon monoxide (201230-82-2) + [N-(p-tolylsulfonyl)imino]phenyliodinane (55962-05-5) → Tosyl isocyanate (4083-64-1)

Guidance literature:

bis(benzonitrile)palladium(II) dichloride; In dichloromethane; acetonitrile; for 0.666667h; under 28502.3 Torr; Ambient temperature;

DOI:10.1016/S0040-4039(00)73576-3

upstream raw materials:

phosgene

toluene-4-sulfonamide

p-toluenesulphonyloxamoyl chloride

isocyanate de chlorosulfonyle

Downstream raw materials:

1-[(4-methylphenyl)sulfonyl]-3-(pyridin-2-yl)urea

1-[(4-methylphenyl)sulfonyl]-3-(pyrimidin-2-yl)urea

N-(6-methyl-[2]pyridyl)-N'-(toluene-4-sulfonyl)-urea

N-(4-methyl-[2]pyridyl)-N'-(toluene-4-sulfonyl)-urea

Refernces

A new and efficient approach to the synthesis of 6-amidino-2-oxopurines

10.1039/b010224p

The research presented in the document focuses on a novel and efficient synthetic approach to 6-amidino-2-oxopurines, which are significant in medicinal chemistry. The study employs the reaction between 5-amino-4-cyanoformimidoylimidazoles and tosyl isocyanate to produce the desired 6-amidino-2-oxopurines with high yields. The reaction's mechanism was explored through additional experiments involving selective acylation of imidazoles and reactivity studies with various compounds. The structures of the synthesized compounds were confirmed using X-ray crystallography, and their properties analyzed through techniques like infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry. The research also discusses the rearrangement of these compounds in the presence of acetic acid and DMF, leading to the formation of pyrimido[5,4-d]pyrimidin-2-one, with the structural confirmation of this compound through X-ray crystallography. The detailed experimental procedures, including the preparation of starting materials, reaction conditions, and analytical methods, are provided, highlighting the use of elemental analysis, spectroscopic data, and crystallographic studies for a comprehensive understanding of the synthesized compounds and their properties.

Cycloaddition reactions of sulfonylisothiocyanates with β,β-disubstituted enamines

10.1016/S0040-4020(01)97399-5

The research focuses on the cycloaddition reactions of sulfonylisothiocyanates with α,β-disubstituted enamines. The purpose of the study was to investigate the formation of cycloadducts and the corresponding dipoles, with a particular emphasis on understanding the structural changes these compounds undergo in different solvents and the factors influencing these transformations. The conclusions drawn from the study indicate that the formation of cycloadducts, rather than dipoles, can be attributed to steric effects, and that the structure of the adducts in solution is significantly influenced by solvent polarity. The researchers also observed a rapid equilibrium between the ring and dipole forms of the compounds, with the rate of conversion being fast compared to the NMR time scale. Key chemicals used in the process include sulfonylisothiocyanates, enamines, tosylisocyanates, and various organic solvents such as CDCl3, CD3CN, and liquid SO2, as well as perchloric acid and acetanhydride for protonation reactions.