Trimethylsilylcarbonitril
TMSCN · TRIMETHYLSILANECARBONITRILE · trimethylsilylformonitrile · CYANOTRIMETHYLSILANE · TRIMETHYLCYANOSILANE · TRIMETHYLSILYLNITRILE · trimethylsilylmethanenitrile · DK897
Identifikatoren & physikalische Daten
| CAS No. | 7677-24-9 |
|---|---|
| Summenformel | C4H9NSi |
| Durchschnittliche Molmasse | 99,21 g/mol |
| Monoisotopische Masse | 99,05042582 g/mol |
| SMILES | C[Si](C)(C)C#N |
| InChIKey | LEIMLDGFXIOXMT-UHFFFAOYSA-N |
| PubChem CID | 82115 |
| EC No. | 231-657-3 |
| DTXSID | DTXSID9064766 |
| Lokaler Name | Trimethylsilylcarbonitril |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 23,8 |
|---|---|
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 81,5 |
| Stoffklassen | Nitrogen Compounds -> Nitriles |
| SpringerMaterials Properties | 29Si nuclear magnetic resonance spectrum |
| Physical Description | Colorless liquidmp = 11-12 deg C[MSDSonline] |
| Schmelzpunkt | 8-11 °C(lit.) |
| Siedepunkt | 114-117 °C(lit.) |
| Dichte | 0.793 g/mL at 20 °C(lit.) |
| Brechungsindex | n20/D 1.392(lit.) |
| Flammpunkt | 34 °F |
| Lagerbedingungen | Inert atmosphere,2-8°C |
| Löslichkeit | Miscible with organic solvents.reacts |
| Aggregatzustand | liquid |
| Wichte | 0.744 |
| Farbe | Yellow |
| BRN | 1737612 |
| Stabilität | Moisture Sensitive |
| InChIKey | LEIMLDGFXIOXMT-UHFFFAOYSA-N |
| CAS Datenbank | 7677-24-9(CAS DataBase Reference) |
| EPA chemische Informationen | Silanecarbonitrile, trimethyl- (7677-24-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P316, P320, P321, P330, P361+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 82 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Silanecarbonitrile, trimethyl-Status: Active Update: 25-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34122Trimethylsilyl cyanide: HSNO Approval: HSR004750 Approved with controls |
| Gefahrenübersicht | Reacts violently with waterHighly toxic by inhalation, skin absorption, and ingestionAn irritant[MSDSonline] See NITRILES. |
| Hazard Classes and Categories | Flam. Liq. 2 (100%) |
| 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) |
| Gesundheitliche Auswirkungen | 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) |
| Unerwünschte Wirkungen | Other Poison - Chemical Asphyxiant |
| Expositionspfade | Inhalation (L96)oral (L96)dermal (L96) |
| Toxizitätsübersicht | Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. 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 Symptoms | Cyanide 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 Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3384 6.1/PG 1 |
| Zollcode | 29310095 |
| R-Sätze (R) | 11-26/27/28-29-50/53 |
| Gefahrensymbole | F,T+,T,N |
| hazard_note | Highly Flammable/Toxic |
| Sicherheitshinweise (S) | 16-36/37/39-45-61-28A-26 |
| Gefahrenklasse | 6.1 |
| Verpackungsgruppe | II |
Anwendungen & Verwendung
Verwenden
Reacts with aldehydes and ketones to give cyanohydrin-TMS ethers which can be reduced to β-aminoethyl alcohols.Trimethylsilyl cyanide (TMSCN) participates in carbonyl aminomethylation via α-silyloxy nitriles.TMSCN can be used as a reagent in the:Trimethylsilyl cyanide was used in the second step of an oxidative Michael addition of cyanide anion to Baylis–Hillman adducts. The importance of the addition of cyanide to α,β-unsaturated carbonyl derivatives is that the products can be converted into a variety of compounds including γ-aminobutyric acids. The reaction took place in a liquid ionic medium ([bmim]Br), which was reused several times without losing its activity. The β-cyano carbonyl compounds were obtained with high regioselectivity and yields (>79%).Cyanosilylation of carbonyl compounds using various catalysts.Synthesis of α-aminonitriles by one-pot, three-component Strecker reaction of ketones with various amines using Brønsted acid catalyst.Cyanation of aryl halides using palladium-complex as a catalyst.
Herstellung & Synthese
synthetische
Trimethylsilyl cyanide, (CH3)3 Si-CN, is obtained by reacting trimethylsilyl chloride with an approximately equimolar amount of an alkali metal cyanide in the absence of water and in the presence of catalytic, sub-stoichiometric amounts of both an alkali metal iodide and N-methylpyrrolidone, at a temperature of from 15°-25° C. Trimethylsilyl cyanide is very toxic. All reactions in this sequence should be carried out in a hood. Preparation of trimethylsilyl cyanide TRIMETHYLSILYL CYANIDE: CYANOSILATION OF p-BENZOQUINONE