Grundinformationen
- Standard-SMILES
[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1- InChIKey
CFOAUYCPAUGDFF-UHFFFAOYSA-N- Summenformel
- C9H9NO2S
- Durchschnittliche Molmasse
- 195,24 g/mol
- Monoisotopische Masse
- 195,03539953
Überblick
Toluenesulfonylmethyl isocyanide is a chemical compound of cyanide.
Namen und Bezeichner
- Bevorzugter Name
- Tosylmethyl isocyanide
- IUPAC
- 1-(isocyanomethylsulfonyl)-4-methylbenzene
- Lokaler Name
- (p-Toluolsulfonyl)methylisocyanid
- Englischer Name
- Tosylmethyl isocyanide
- Summenformel
- C9H9NO2S
- Molmasse
- 195.24
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
36635-61-7- PubChem CID
- 161915
- DTXSID
DTXSID90190101- UNII
- C35FD6OLH8
- EC Number
- 253-140-1
- Nikkaji
- J2.201.925B、J209.011B
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,3
- Polarare Oberfläche (TPSA)
- 46,9 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 298
Experimentelle und physikochemische Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 109 · 109-113 °C(lit.)
- Dichte
- 1.2721 · 1.2721 (rough estimate)
- Brechungsindex
- 1.527 · 1.5270 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- water: slightly soluble
- Aggregatzustand
- Liquid
- Farbe
- Clear
- Wasserlöslichkeit
- insoluble
- Merck
- 14 · 14,9556
- BRN
- 3592382 · 3592382
- InChI
- InChI=1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
- InChIKey
- BBNNLJMGPASZPD-UHFFFAOYSA-N
- SMILES
- S(C1C=CC(C)=CC=1)(=O)(=O)C[N+]#[C-]
- CAS Datenbank
- 36635 · 36635-61-7(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 1.1% (1 of 93) of reports.
Danger
H301+H311+H331 (31.2%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P203, P233, P260, P261, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P342+P316, P361+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 93 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: Benzene, 1-[(isocyanomethyl)sulfonyl]-4-methyl-
Status: Active Update: 08-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/22098
4-Toluenesulphonylmethyl isocyanide: HSNO Approval: HSR004315 Approved with controls
Toxikologische Informationen
Treatment
Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)
Health Effects
Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)
Toxicity Summary
Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
Sicherheitsdaten
- F
- 21
- wgk
- 3
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29299000
- risk_code
- 23/24/25
- hazard_code
- T,Xi
- hazard_note
- Irritant
- safety_code
- 36/37-45-38-36/37/39-28A
- hazard_class
- 6.1(b)
- packing_group
- III
- Speicherklasse
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- Acute Tox. 2 DermalAcute Tox. 2 InhalationAcute Tox. 2 Oral
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
Verwendung und Herstellung
Anwendungen
BeschreibungTosylmethyl 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.
VerwendenTosylmethyl 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.
Darstellung
synthetischeN-(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.
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Ergänzende Hinweise
DefinitionTosylmethyl isocyanide is a chemical compound of cyanide that Versatile synthon in organic chemistry, especially in the synthesis of heterocyclic Compounds.
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