Trimethylsilyl isothiocyanate

Base Information

• Chemical Name: Trimethylsilyl isothiocyanate
• CAS No.: 2290-65-5
• Molecular Formula: C4H9NSSi
• Molecular Weight: 131.274
• Hs Code.: 29319090
• European Community (EC) Number: 218-929-7
• UNII: JK38S9F7MN
• DSSTox Substance ID: DTXSID4062307
• Nikkaji Number: J213.167F
• Mol file: 2290-65-5.mol

Synonyms:TMS-ITC;trimethylsilylisothiocyanate

Chemical Property of Trimethylsilyl isothiocyanate

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 6.83mmHg at 25°C
• Melting Point: 32.8 °C
• Refractive Index: n20/D 1.482(lit.)
• Boiling Point: 143 °C at 760 mmHg
• Flash Point: 17 °C
• PSA: 44.45000
• Density: 0.89 g/cm³
• LogP: 1.92410
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Reacts with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 131.02249700
• Heavy Atom Count: 7
• Complexity: 98.7

Purity/Quality:

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

Trimethylsilyl isothiocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 10-23/24/25-36/37/38-42
• Safety Statements: 23-26-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)N=C=S
• Uses: Trimethylsilyl isothiocyanate is used as derivatizing reagent during the synthesis of amino acid thiohydantoins. It participates in ring opening reaction of N-substituted aziridines and cyclohexene oxide. Trimethylsilyl isothiocyanate was used as derivatizing reagent during the synthesis of amino acid thiohydantoins.

Technology Process of Trimethylsilyl isothiocyanate

There total 35 articles about Trimethylsilyl isothiocyanate 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: 98.0%

chloro-trimethyl-silane (75-77-4) + potassium thioacyanate (333-20-0) → trimethylsilyl isothiocyanate (2290-65-5)

Guidance literature:

With 18-crown-6 ether; at 20 - 120 ℃;

DOI:10.1002/chem.201000289

Reference yield: 96.0%

trimethylsilyl cyanide (7677-24-9) + bis-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinan-2-yl)disulfide (4073-59-0) → trimethylsilyl isothiocyanate (2290-65-5) + bis-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinan-2-yl)sulfide (4090-54-4)

Guidance literature:

In dichloromethane; for 240h; Ambient temperature;

Reference yield: 95.0%

O,O-diethyl S-(trimethylsilyl) phosphorodithioate (18306-95-1) + 2-isothiocyanato-4,5-dimethyl-1,3,2-dioxaphospholane (87290-46-8) → trimethylsilyl isothiocyanate (2290-65-5) + thioanhydride of O,O-diethyl hydrogen phosphorodithioate and O,O-(1,2-dimethylethylene) hydrogen phosphorothioite

Guidance literature:

at 25 - 30 ℃;

upstream raw materials:

chloro-trimethyl-silane

sodium thiocyanide

ammonium thiocyanate

lead(II) thiocyanate

Downstream raw materials:

trimethylsilyl trifluoroacetate

trimethylsilyl isocyanate

2-benzylimino-thiazole-3-carbothioic acid ethylcarbamoyl-amide

phosphoryl-isothiocyanate

Refernces

A mild copper-catalyzed aerobic oxidative thiocyanation of arylboronic acids with TMSNCS

10.1039/c4ob02208d

The research focuses on the development of a mild and efficient method for the conversion of arylboronic acids into arylthiocyanates using a copper-catalyzed aerobic oxidative process. The study employs trimethylsilylisothiocyanate (TMSNCS) as a thiocyantion reagent and utilizes NaF as a promoter under an oxygen atmosphere, with CuCl serving as the catalyst. The cross-coupling reaction is conducted at ambient temperature and is found to be effective for a broad range of functional groups, including strong electron-withdrawing groups. The experiments involve the optimization of reaction conditions, including the evaluation of various catalysts, ligands, additives, and solvents, ultimately leading to the identification of an optimal condition that involves the use of 20 mol% CuCl, 20 mol% TMEDA as a ligand, 1 equiv. of NaF, and 4 equiv. of K2CO3 in acetonitrile at room temperature for 12 hours, with 3? molecular sieves. The substrate scope was also investigated, demonstrating the versatility of the method with both electron-donating and electron-withdrawing arylboronic acids. The reaction mechanism is proposed based on the formation and reactivity of CuSCN as an intermediate, with both TMEDA and O2 being essential for the transformation. The study concludes that the developed protocol offers a milder and more efficient approach for aromatic oxidative thiocyanation, with potential applications in the synthesis of a variety of aryl thiocyanates.