4083-64-1 Usage
Chemical Description
Tosyl isocyanate is an organic compound with the formula CH3C6H4SO2NCO.
Description
Tosyl isocyanate, also known as p-Toluenesulfonyl isocyanate, is a chemical reagent with the chemical formula C7H7NO2S. It is a clear liquid that undergoes palladium-catalyzed bis-allylation reactions with allylstannanes and allyl chlorides. Tosyl isocyanate is widely used in the synthesis of various organic compounds due to its unique reactivity and versatility.
Uses
1. Used in Organic Synthesis:
Tosyl isocyanate is used as a reagent for the preparation of acetylated syn-1,2-diols, which are important intermediates in organic chemistry. It is also used in the synthesis of oxazolidin-2-ones, 2,3-diamino acids, and N-tosylcarbonamides, which are valuable building blocks for the development of pharmaceuticals and other bioactive compounds.
2. Used in Pharmaceutical Analysis:
Tosyl isocyanate has been employed as a derivatization reagent in the determination of 3-α-hydroxy tibolone in human plasma by LC-MS/MS. This application highlights its utility in enhancing the detection and analysis of specific compounds in complex biological samples.
3. Used in Quality Control of Pharmaceutical Products:
In the pharmaceutical industry, Tosyl isocyanate is used as a derivatization reagent in the simultaneous quantitative analysis of diethylene glycol and propylene glycol in pharmaceutical products by HPLC. This application is crucial for ensuring the quality, safety, and efficacy of pharmaceutical formulations.
4. Used in Chemical Research:
Due to its unique chemical properties, Tosyl isocyanate is also used in academic and industrial research settings to explore new reaction pathways, develop novel synthetic methods, and create innovative compounds with potential applications in various fields, including materials science, pharmaceuticals, and agrochemicals.
Synthesis Reference(s)
Tetrahedron Letters, 35, p. 9609, 1994 DOI: 10.1016/0040-4039(94)88523-0
Hazard
Moderately toxic by ingestion. Low toxicity by inhalation. A mild skin and moderate eye
irritant.
Synthesis
Add the organic azide (0.75 mmol), Pd(OAc)2
(5.6 mg, 5 mol%) to an oven-dried Schlenk tube (10 mL). Purge the tube
and backfill with CO (three cycles) from a balloon. Inject anhydrous
MeCN (3.0 mL) into the tube. Stir at 80°C for 4 h under CO atmosphere
(balloon). Concentrate the mixture under reduced pressure. Purify the
residue by column chromatography (petroleum ether/EtOAc 3:1.-.1:1).
Check Digit Verification of cas no
The CAS Registry Mumber 4083-64-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,8 and 3 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 4083-64:
(6*4)+(5*0)+(4*8)+(3*3)+(2*6)+(1*4)=81
81 % 10 = 1
So 4083-64-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H7NO3S/c1-7-2-4-8(5-3-7)13(11,12)9-6-10/h2-5H,1H3
4083-64-1Relevant articles and documents
Carbonylation of Selenilimines to Arylsulfonyl Isocyanates
Besenyei, Gabor,Nemeth, Sandor,Simandi, Laszlo I.
, p. 9609 - 9610 (1994)
Selenilimines of general formula ArSO2N=SePh2, 1, can be catalytically carbonylated to arylsulfonyl isocyanates, 2, in the presence of palladium complexes as catalysts.This transformation represents a new two-step oxidative N-carbonylation reaction.
Pd-catalyzed amidation of 1,3-diketones with CO and azidesviaa nitrene intermediate
Gu, Zheng-Yang,Chen, Jie,Xia, Ji-Bao
, p. 11437 - 11440 (2020/10/12)
An efficient Pd-catalyzed amidation of 1,3-diketones has been developed using carbon monoxide and organic azides. This reaction provides a step-economic approach to produce β-ketoamides from readily available compounds under mild ligand-, oxidant-, and base-free conditions. The mechanistic studies showed that the reaction occurred through anin situgenerated isocyanate intermediate.
Syntheses of isocyanates via amines and carbonyl fluoride
Quan, Hengdao,Zhang, Ni,Zhou, Xiaomeng,Qian, Hua,Sekiya, Akira
, p. 26 - 30 (2015/06/08)
Isocyanates are widely used in many different areas, but the most common synthesis route-phosgene route cannot fit the more and more rigorous restriction of safety and environment. Here, a facile synthesis method of isocyanates via amines and carbonyl fluoride is proven feasibly by expanding its applications to the syntheses of nine different isocyanates. And two differences with the phosgene route are proposed. The reaction could occur under milder conditions and afford isocyanates in good yields, especially for the isocyanates containing electron withdrawing groups. It is appealing for industrial application.