36635-61-7 Usage
Description
Tosylmethyl isocyanide, also known as TosMIC, is an organic compound that serves as a versatile synthetic reagent in the field of organic chemistry. It is a pale yellow to light brown crystalline powder and is particularly useful in the preparation of biologically active heterocycles such as pyrroles and imidazoles. Tosylmethyl isocyanide is also reported to inhibit [Fe]-hydrogenase with very high affinity.
Uses
Used in Pharmaceutical Industry:
Tosylmethyl isocyanide is used as a synthetic reagent for the preparation of biologically active pyrroles and imidazoles, which are important in the development of new drugs and pharmaceutical compounds. Its ability to inhibit [Fe]-hydrogenase makes it a promising candidate for applications in drug discovery and design.
Used in Organic Chemistry Research:
As a versatile synthon in organic chemistry, Tosylmethyl isocyanide is employed in the synthesis of a variety of heterocyclic compounds. Its unique chemical properties allow for the creation of complex molecular structures that can be used in various research applications, including the development of new materials and the study of chemical reactions.
Used in Chemical Synthesis:
Tosylmethyl isocyanide is used as a reagent in the preparation of biologically active heterocycles, which are essential components in the synthesis of various chemical compounds. Its high affinity for [Fe]-hydrogenase inhibition makes it a valuable tool in the development of new chemical processes and the improvement of existing ones.
Preparation
N-(p-Tolylsulfonylmethyl)formamide 1609:
A 3-L, three-necked, round-bottomed flask, equipped with a mechanical stirrer, a condenser, and a thermometer, was charged with sodium p-toluenesulfinate 1606 (267 g, 1.5 mol). After the addition of water (750 mL), a 34–37% solution of formaldehyde 1607 (350 mL, 378 g, ca. 4.4 mol), formamide 1608 (600 mL, 680 g, 15 mol), and formic acid (200 mL, 244 g, 5.3 mol), the stirred reaction mixture was heated at 90 C°. The sodium p-toluenesulfinate dissolved during the heating, and the clear solution was kept at 90–95 C° for 2 h. It was then cooled in an ice/salt bath with continued stirring and further cooled overnight in a freezer at 20 C°. The white solid produced was collected by suction filtration. It was washed thoroughly in a beaker by stirring with three 250 mL portions of iced water. The product was dried under reduced pressure over phosphorus pentoxide at 70 C° to provide 134–150 g (42–47%) of crude N-(p-tolylsulfonylmethyl)formamide 1609; mp 106–110 C°. This product was sufficiently pure to be used directly in the following reaction.
Purification Methods
Use an efficient fume cupboard. Purify TOSMIC by dissolving (50g) in CH2Cl2 (150mL) and passing it through a column (40x3cm) containing neutral alumina (100g) in CH2Cl2 and eluting with CH2Cl2. A nearly colourless solution (700mL) is collected, evaporated in vacuo and the residue (42-47g) of TOSMIC (m 113-114o dec) is recrystallised once from MeOH (m 116-117o dec). [Hoogenboom et al. Org Synth 57 102 1977, Lensen Tetrahedron Lett 2367 1972.] It also crystallises from EtOH (charcoal) [Saito & Itano, J Chem Soc, Perkin Trans 1 1 1986].
Check Digit Verification of cas no
The CAS Registry Mumber 36635-61-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,6,6,3 and 5 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 36635-61:
(7*3)+(6*6)+(5*6)+(4*3)+(3*5)+(2*6)+(1*1)=127
127 % 10 = 7
So 36635-61-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
36635-61-7Relevant articles and documents
Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas
Yang, Zheng-Lin,Xu, Xin-Liang,Chen, Xue-Rong,Mao, Zhi-Feng,Zhou, Yi-Feng
, p. 648 - 652 (2020/12/21)
Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.
Phenyl pyrrole compound and application thereof in bactericidal activity
-
, (2020/08/17)
The invention provides a novel phenyl pyrrole compound, and the phenyl pyrrole compound shows good bactericidal activity and can be used for preparing a broad-spectrum plant bactericide. In addition,the synthesis route is simple, the operation is convenient, the synthesis cost is reduced, and ecological environment pollution to soil, surface water, underground water and the like is avoided.
Catalytic Enantio- and Diastereoselective Mannich Addition of TosMIC to Ketimines
Franchino, Allegra,Chapman, Jack,Funes-Ardoiz, Ignacio,Paton, Robert S.,Dixon, Darren J.
supporting information, p. 17660 - 17664 (2018/11/10)
Chiral amines bearing a stereocenter in the α position are ubiquitous compounds with many applications in the pharmaceutical and agrochemical sectors, as well as in catalysis. Catalytic asymmetric Mannich additions represent a valuable method to access such compounds in enantioenriched form. This work reports the first enantio- and diastereoselective addition of commercially available p-toluenesulfonylmethyl isocyanide (TosMIC) to ketimines, affording 2-imidazolines bearing two contiguous stereocenters, one of which is fully-substituted, with high yields and excellent stereocontrol. The reaction, catalyzed by silver oxide and a dihydroquinine-derived N,P-ligand, is broad in scope, operationally simple, and scalable. Derivatization of the products provides enantioenriched vicinal diamines, precursors to NHC ligands and sp3-rich heterocyclic scaffolds. Computations are used to understand catalysis and rationalize stereoselectivity.