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 99% ^*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:

phosphoryl-isothiocyanate

CF₄N₂P₂S₂

1-thiocyanato-3-methyl-2-butene

1-isothiocyanato-3-methyl-2-butene

Refernces

• 1、 Bl?sing, Kevin,Bresien, Jonas,Maurer, Steffen,Schulz, Axel,Villinger, Alexander. "Trimethylsilyl Pseudohalide Adducts of GaCl3 and B(C6F5)3". supporting information. p. 1913 - 1920. Retrieved 2021/05/10.
• 2、 Chechik, Victor,Conte, Marco,Dransfield, Trevor,North, Michael,Omedes-Pujol, Marta. "Cyanogen formation during asymmetric cyanohydrin synthesis". supporting information; scheme or table. p. 3372 - 3374. Retrieved 2010/08/07.