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Tosylmethyl isocyanide

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CAS:36635-61-7
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Tosylmethyl isocyanide Basic information
Product Name:Tosylmethyl isocyanide
Synonyms:1-[(isocyanomethyl)sulfonyl]-4-methyl-benzen;Tosylmethyl isocyani;Isocyanomethyl 4-methylphenyl sulphone;4-[(Isocyanomethyl)sulphonyl]toluene, (Toluene-4-sulphonyl)methyl isocyanide;(p-Toluensulfonyl)methylisocyanide;(p-Tolylsulfonyl)methyl isocyanide, TosMIC, Tosylmethyl isocyanide;(4-Methylphenylsulfonylmethyl) isocyanide;4-Methylphenylsulfonylmethyl isocyanide
CAS:36635-61-7
MF:C9H9NO2S
MW:195.24
EINECS:253-140-1
Product Categories:cyanide;Building Blocks;Chemical Synthesis;Isocyanides;Nitrogen Compounds;Organic Building Blocks;Tesaglitazar Carbjdopa;Tosmic;Aliphatics;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Boron, Nitrile, Thio,& TM-Cpds;Benzene derivatives;36635-61-7
Mol File:36635-61-7.mol
Tosylmethyl isocyanide Structure
Tosylmethyl isocyanide Chemical Properties
Melting point 109-113 °C(lit.)
density 1.2721 (rough estimate)
refractive index 1.5270 (estimate)
storage temp. 2-8°C
solubility water: slightly soluble
form Liquid
color Clear
Water Solubility insoluble
Sensitive Moisture Sensitive
Merck 14,9556
BRN 3592382
Exposure limitsNIOSH: IDLH 25 mg/m3
InChIInChI=1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
InChIKeyBBNNLJMGPASZPD-UHFFFAOYSA-N
SMILESS(C1C=CC(C)=CC=1)(=O)(=O)C[N+]#[C-]
CAS DataBase Reference36635-61-7(CAS DataBase Reference)
Safety Information
Hazard Codes T,Xi
Risk Statements 23/24/25
Safety Statements 36/37-45-38-36/37/39-28A
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
21
Hazard Note Irritant
HazardClass 6.1(b)
PackingGroup III
HS Code 29299000
MSDS Information
ProviderLanguage
(p-Tolylsulfonyl)methyl isocyanide English
SigmaAldrich English
ACROS English
ALFA English
Tosylmethyl isocyanide Usage And Synthesis
DescriptionTosylmethyl isocyanide is a versatile synthon in organic chemistry, widely used as a reagent for the preparation of biologically active pyrroles and imidazoles. Tosylmethyl isocyanide undergoes a base-promoted 1,3-dipolar cycloaddition reaction with immobilised imines under microwave irradiation to give 1,5-disubstituted imidazoles.
Chemical PropertiesPale yellow to light brown crystalline powder
UsesTosylmethyl Isocyanide is used as a synthetic reagent in the preparation of variety or biologically active heterocycles such as pyrroles and imidazoles. Tosylmethyl Isocyanide is reported to inhibit [ Fe]-hydrogenase with very high affinity.
DefinitionTosylmethyl isocyanide is a chemical compound of cyanide that Versatile synthon in organic chemistry, especially in the synthesis of heterocyclic Compounds.
PreparationN-(p-Tolylsulfonylmethyl)formamide 1609:
36635-61-7 synthesis
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.
ApplicationTosylmethyl isocyanide was used:
(1) in the synthesis of triplet drugs with the 1,3,5-trioxazatriquinane skeleton;
(2) as reagent in the preparation of biologically active pyrroles and imidazoles;
(3) as the isonitrile component in a diastereoselective Passerini reaction employing sugar-derived aldehydes.
Purification MethodsUse 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].
Tag:Tosylmethyl isocyanide(36635-61-7) Related Product Information
Methylparaben Methyl acrylate Molybdic acid Sulfosulfuron Kresoxim-methyl Basic Violet 1 Ammonium acetate Ammonium carbonate Ammonium sulfate Paraquat dichloride Ammonium dihydrogen phosphate Tosyl cyanide Acetonitrile Methanol p-Tolunitrile Methyl acetate Ammonium hydroxide Ammonium chloride