Trimethylsilylcarbonitril

Trimethylsilyl cyanide

HCID 82115CAS 7677-24-9

Grundinformationen

Standard-SMILES
C[Si](C)(C)C#N
InChIKey
LEIMLDGFXIOXMT-UHFFFAOYSA-N
Summenformel
C4H9NSi
Durchschnittliche Molmasse
99,21 g/mol
Monoisotopische Masse
99,05042582

Überblick

Trimethylsilyl cyanide is a chemical compound of cyanide. It is used in organic synthesis. (L106)

Namen und Bezeichner

Bevorzugter Name
Trimethylsilyl cyanide
IUPAC
trimethylsilylformonitrile
Lokaler Name
Trimethylsilylcarbonitril
Englischer Name
Trimethylsilyl cyanide
Summenformel
C4H9NSi
Molmasse
99.21

Namen und Synonyme

Trimethylsilyl cyanide7677-24-9TrimethylsilanecarbonitrileSilanecarbonitrile, trimethyl-TrimethylsilylnitrileTMSCNTrimethylsilylcarbonitrileDTXSID9064766RefChem:899908DTXCID4047915231-657-3Cyanotrimethylsilane
Weitere Namen anzeigen
trimethylsilylmethanenitrileDK897TrimethylsilanecarTrimethyl cyanogen
TrimethylsilylcyanidetrimethylsilylformonitriletrimethylcyanosilaneC4H9NSiMFCD00001765trimethylsilane carbonitrileTrimethylsilylCyanide-13C,15NTMS cyanide

Datenbank-Bezeichner

CAS
7677-24-9
PubChem CID
82115
DTXSID
DTXSID9064766
UNII
X7M2DZS7WZ
EC Number
231-657-3
Nikkaji
J81.438E

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
23,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
6

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Nitriles
SpringerMaterials Properties29Si nuclear magnetic resonance spectrum
Physical DescriptionColorless liquid; mp = 11-12 deg C; [MSDSonline]

Physikochemische Eigenschaften

Schmelzpunkt
8 · 8-11 °C(lit.)
Siedepunkt
114 · 114-117 °C(lit.)
Dichte
0.793 g/mL · 0.793 g/mL at 20 °C(lit.)
Brechungsindex
20 · n20/D 1.392(lit.)
Flammpunkt
34 °F · 34 °F
storage temp.
2 · Inert atmosphere,2-8°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H225 (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.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: Silanecarbonitrile, trimethyl-

Status: Active Update: 25-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34122

Trimethylsilyl cyanide: HSNO Approval: HSR004750 Approved with controls

Hazards SummaryReacts violently with water; Highly toxic by inhalation, skin absorption, and ingestion; An irritant; [MSDSonline] See NITRILES.
Hazard Classes and CategoriesFlam. Liq. 2 (100%)

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)

Adverse EffectsOther Poison - Chemical Asphyxiant
Exposure RoutesInhalation (L96) ; oral (L96) ; dermal (L96)
Toxicity Summary · 1 Eintrag

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 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)

Sicherheitsdaten

F
10-21
wgk
3
tsca
TSCA listed
ridadr
UN 3384 6.1/PG 1
hs_code
29310095
risk_code
11-26/27/28-29-50/53

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed 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

UsesTrimethylsilyl cyanide is used in organic synthesis. (L106)
General Manufacturing InformationSilanecarbonitrile, trimethyl-: ACTIVE
Anwendungen · 1 Eintrag

VerwendenReacts 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.

Darstellung · 1 Eintrag

synthetischeTrimethylsilyl 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

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