Trimethylsilyl cyanide

Base Information

• Chemical Name: Trimethylsilyl cyanide
• CAS No.: 7677-24-9
• Molecular Formula: C4H9NSi
• Molecular Weight: 99.2077
• Hs Code.: 29310095
• European Community (EC) Number: 231-657-3
• DSSTox Substance ID: DTXSID9064766
• Nikkaji Number: J81.438E
• Wikipedia: Trimethylsilyl_cyanide
• Wikidata: Q3008073
• Mol file: 7677-24-9.mol

Synonyms:TMSCN;trimethylsilyl cyanide

Chemical Property of Trimethylsilyl cyanide

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 16.6mmHg at 25°C
• Melting Point: 8-11 °C(lit.)
• Refractive Index: n20/D 1.392(lit.)
• Boiling Point: 118.499 °C at 760 mmHg
• Flash Point: 1.111 °C
• PSA: 23.79000
• Density: 0.802 g/cm³
• LogP: 1.38738
• Storage Temp.: 0-6°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with organic solvents.
• Water Solubility.: reacts
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 99.050425826
• Heavy Atom Count: 6
• Complexity: 81.5

Purity/Quality:

99% ^*data from raw suppliers

Trimethylsilyl cyanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T+,T,N
• Hazard Codes: F,T+,T,N
• Statements: 11-26/27/28-29-50/53
• Safety Statements: 16-36/37/39-45-61-28A-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C[Si](C)(C)C#N
• Physical properties: Trimethylsilane cyanide is a colorless volatile liquid with almond odor, soluble in most organic solvents, such as dichloromethane, chloroform, etc.; it reacts violently with protic solvents such as water. This compound is used in organic synthesis as a replacement reagent for highly toxic HCN to introduce cyano groups into molecules.
• Uses: Cyanotrimethylsilane is a highly versatile reagent that reacts with a multitude of functional groups to yield an array of products and/or highly valuable synthetic intermediates.Aldehydes and ketones are readily transformed into the corresponding cyanohydrin trimethylsilyl ethers when treated with cyanotrimethylsilane in the presence of Lewis acids (eq 1), triethylamine,or solid bases such as CaF2 or hydroxyapatite. The products can be readily hydrolyzed to the corresponding cyanohydrins. The cyanosilylation of aromatic aldehydes can be achieved with high enantioselectivity in the presence of catalytic amounts of a modified Sharpless catalyst consisting of titanium tetraisopropoxide and L-(+)-diisopropyl tartrate (eq 2).Catalysis with chiral titanium reagents yields aliphatic and aromatic cyanohydrins in high chemical and optical yields (eq 3). Cyanohydrins can be subsequently transformed into a variety of useful synthetic intermediates (eq 4). 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 Br?nsted acid catalyst. Cyanation of aryl halides using palladium-complex as a catalyst. Trimethylsilyl Cyanide is used as a reagent in the synthesis of optically active cyanohydrins. Used in the preparation of Reissert compounds, which represent reactive polyamides. Toxic to humans.

Technology Process of Trimethylsilyl cyanide

There total 54 articles about Trimethylsilyl cyanide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

bis(trimethylsilyl)sulphate (18306-29-1) + potassium cyanide (151-50-8) → trimethylsilyl cyanide (7677-24-9)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; at 200 ℃;

DOI:10.1055/s-1980-29051

Reference yield: 93.0%

trimethylsilyl bromide (2857-97-8) + bis(triphenylphosphine)iminium cyanide (65300-07-4) → trimethylsilyl cyanide (7677-24-9)

Guidance literature:

at 20 ℃; for 1h;

Reference yield: 88.0%

chloro-trimethyl-silane (75-77-4) + potassium cyanide (151-50-8) → trimethylsilyl cyanide (7677-24-9)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; potassium iodide; for 12h; Ambient temperature;

DOI:10.1055/s-1982-29804

upstream raw materials:

chloro-trimethyl-silane

hydrogen cyanide

silver(I) cyanide

hexamethyldisilathiane

Downstream raw materials:

2,2-diphenyl-2-(trimethylsiloxy)ethanenitrile

C₁₀H₂₀N₂OSi

2-bromo-2-methylpropanoyl cyanide

C₆H₉F₃N₂OSi

Refernces

• 1、 Rasmussen,Heilmann. "". . p. 523. Retrieved 1979.
• 2、 Lambert, Joseph B.,McConnell, JoAnn A.,Schilf, Wojciech,Schulz, William J.. "Free and Assosiated Trimethylsilyl Cation in Solution". . p. 455 - 456. Retrieved 1988.
• 3、 Landmann, Johannes,Sprenger, Jan A. P.,Hennig, Philipp T.,Bertermann, Rüdiger,Grüne, Matthias,Würthner, Frank,Ignat'ev, Nikolai V.,Finze, Maik. "Perfluoroalkyltricyanoborate and Perfluoroalkylcyanofluoroborate Anions: Building Blocks for Low-Viscosity Ionic Liquids". supporting information. p. 608 - 623. Retrieved 2017/11/21.
• 4、 -. "IONIC COMPOUND, PROCESS FOR PRODUCING SAME, AND ION-CONDUCTIVE MATERIAL COMPRISING SAME". Page/Page column 44. . Retrieved 2011/06/23.