(p-Toluolsulfonyl)methylisocyanid

Tosylmethyl isocyanide

HCID 161915CAS 36635-61-7

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

Tosylmethyl isocyanide36635-61-7TosMICp-Toluenesulfonylmethyl isocyanide4-Toluenesulfonylmethyl isocyanide(p-Tolylsulfonyl)methyl isocyanideTMIC isocyanideC35FD6OLH8p-toluenesulphonylmethyl isocyanideNSC-631633DTXSID90190101RefChem:190488
Weitere Namen anzeigen
isocyanideToluenesulfonyl Methyl isocyanideTosylmethyl isocyaniTosylmethy isocyanide ,98%TOLUENE-4-SULFONYLMETHYL ISOCYANIDE
DTXCID60112592253-140-11-((Isocyanomethyl)sulfonyl)-4-methylbenzene1-(isocyanomethylsulfonyl)-4-methylbenzene4-Toluenesulphonylmethyl IsocyanideTosylmethylisocyanide1-isocyanomethanesulfonyl-4-methylbenzeneMFCD00000005

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

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds
Physical DescriptionSolid; [Merck Index] Light brown powder; [Alfa Aesar MSDS]

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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 · 3 Einträge

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

Hazards SummaryMay cause irritation; Toxic by ingestion, inhalation, and skin absorption; [Alfa Aesar MSDS] See Ethyl isocyanide and Phenylisocyanide.
Hazard Classes and CategoriesAcute Tox. 3 (91.4%)

Toxikologische Informationen

Treatment · 1 Eintrag

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 · 1 Eintrag

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)

Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)
Toxicity Summary · 1 Eintrag

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)

Signs and SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

F
21
wgk
3
ridadr
UN 2811 6.1/PG 3
hs_code
29299000
risk_code
23/24/25
hazard_code
T,Xi

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

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

UsesUsed in organic synthesis; [Merck Index]
Anwendungen · 2 Einträge

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 · 1 Eintrag

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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