(Trimethylsilyl)acetonitrile

Base Information

• Chemical Name: (Trimethylsilyl)acetonitrile
• CAS No.: 18293-53-3
• Molecular Formula: C5H11NSi
• Molecular Weight: 113.235
• Hs Code.: 29310099
• European Community (EC) Number: 242-169-5
• UNII: 5XB7XHD8BU
• DSSTox Substance ID: DTXSID60171361
• Nikkaji Number: J266.101B
• Wikidata: Q83041438
• Mol file: 18293-53-3.mol

Synonyms:(Trimethylsilyl)acetonitrile;18293-53-3;2-(trimethylsilyl)acetonitrile;TRIMETHYLSILYLACETONITRILE;2-TRIMETHYLSILYLACETONITRILE;Acetonitrile, 2-(trimethylsilyl)-;Acetonitrile, (trimethylsilyl)-;C5H11NSi;5XB7XHD8BU;EINECS 242-169-5;MFCD00001882;Acetonitrile,2-(trimethylsilyl)-;(Cyanomethyl)trimethylsilane;TMSCH2CN;UNII-5XB7XHD8BU;trimethylsilyl acetonitrile;trimethylsilyl(acetonitrile);trimethylsilanyl-acetonitrile;SCHEMBL195841;C5-H11-N-Si;Trimethylsilylacetonitrile, 97%;DTXSID60171361;(Trimethylsilyl)acetonitrile, 99%;AC8644;AKOS009158527;AS-77908;SY107268;CS-0120673;FT-0660852;EN300-57101;A905277;J-011708

Chemical Property of (Trimethylsilyl)acetonitrile

Chemical Property:

• Vapor Pressure: 2.19mmHg at 25°C
• Refractive Index: n20/D 1.420(lit.)
• Boiling Point: 162.2 °C at 760 mmHg
• Flash Point: 50 °C
• PSA: 23.79000
• Density: 0.807 g/cm³
• LogP: 1.84818
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Sol most common organic solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 113.066075890
• Heavy Atom Count: 7
• Complexity: 92.4

Purity/Quality:

98%,99%, ^*data from raw suppliers

(Trimethylsilyl)acetonitrile 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 10-23/24/25-36/37/38
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)CC#N
• Physical properties: bp 84–85 °C/54 mmHg, 66 °C/35 mmHg, 65–70 °C/20 mmHg;3 d 0.827 g cm?3.
• Uses: α-carbanion is a useful alternative to LiCH2CN for nucleophilic cyanomethylation; (Z)-selective Peterson alkenation). Trimethylsilylacetonitrile participates in the following synthesis reactions: Metalation, Peterson Alkenation (Cyanomethylenation), Michael Addition, Reactions with Other Electrophiles, Cyanomethylation, Metal-Catalyzed Reactions etc. (Trimethylsilyl)acetonitrile has been used in catalytic cyanomethylation of various carbonyl compounds in the presence of Lewis bases.

Technology Process of (Trimethylsilyl)acetonitrile

There total 15 articles about (Trimethylsilyl)acetonitrile 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: 99.0%

trimethylsilyl iodide (16029-98-4) + N-methyl-N,N-bis(1-silatranylmethyl)amine (382156-74-3) → 2-trimethylsilylacetonitrile (18293-53-3) + N-methyl-N,N-bis(silatranylmethyl)amine hydroiodide

Guidance literature:

In acetonitrile; at 25 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.jorganchem.2020.121319

Reference yield: 96.0%

chloro-trimethyl-silane (75-77-4) + acetonitrile (75-05-8,26809-02-9) + N-methyl-N,N-bis(1-silatranylmethyl)amine (382156-74-3) → 2-trimethylsilylacetonitrile (18293-53-3) + N-methyl-N,N-bis(silatranylmethyl)amine hydrochloride (1137520-51-4)

Guidance literature:

In acetonitrile; at 25 ℃; for 4h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.jorganchem.2020.121319

Reference yield: 70.0%

chloro-trimethyl-silane (75-77-4) + chloroacetonitrile (107-14-2) → 2-trimethylsilylacetonitrile (18293-53-3)

Guidance literature:

With zinc;

upstream raw materials:

ethanedinitrile

(trimethylsilyl)methylmagnesium chloride

sodium cyanide

Chloromethyltrimethylsilane

Downstream raw materials:

3-phenyl-2-(trimethylsilyl)propionitrile

cinnamonitrile

cinnamic nitrile

(Z)-cinnamonitrile

Refernces

• 1、 -. "Preparation method 1,4-cyano -2-butene". Paragraph 0017; 0021. . Retrieved 2020/04/17.
• 2、 Hirono, Yutaro,Kobayashi, Koji,Yonemoto, Misato,Kondo, Yoshinori. "Metal-free deprotonative functionalization of heteroaromatics using organic superbase catalyst". supporting information; experimental part. p. 7623 - 7624. Retrieved 2010/12/19.