2290-65-5

Basic information

• Product Name: TRIMETHYLSILYL ISOTHIOCYANATE
• Synonyms: isothiocyanatotrimethyl-silan;Silane, isothiocyanatotrimethyl-;TRIMETHYLSILYL ISOTHIOCYANATE;ISOTHIOCYANATOTRIMETHYLSILANE;Trimethylsilylisothiocyanate,94%;Trimethylsilyl isothiocyanate,97%;(TriMethylsilyl)isothiocyanate 99%
• CAS NO: 2290-65-5
• Molecular Formula: C₄H₉NSSi
• Molecular Weight: 131.27
• EINECS: 218-929-7
• Mol File: 2290-65-5.mol
• Article Data: 18

Chemical Properties

• Melting Point: −32.8 °C(lit.)
• Boiling Point: 143 °C(lit.)
• Flash Point: 95 °F
• Appearance: /liquid
• Density: 0.931 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 6.83mmHg at 25°C
• Refractive Index: n20/D 1.482(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 1745262
• CAS DataBase Reference: TRIMETHYLSILYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLSILYL ISOTHIOCYANATE(2290-65-5)
• EPA Substance Registry System: TRIMETHYLSILYL ISOTHIOCYANATE(2290-65-5)

Safety Data

• Hazard Codes: T
• Statements: 10-23/24/25-36/37/38-42
• Safety Statements: 23-26-36/37-45
• RIDADR: UN 1992 3/PG 3
• WGK Germany: 3
• F: 10-19-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 2290-65-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

Different sources of media describe the Uses of 2290-65-5 differently. You can refer to the following data:
1. 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.
2. Trimethylsilyl isothiocyanate was used as derivatizing reagent during the synthesis of amino acid thiohydantoins.

General Description

Trimethylsilyl isothiocyanate (TMS-ITC) reacts with fullerene-mixed peroxide C60(O)(OOtBu)4 to yield isothiocyanate derivative C60(NCS)(OH)(OOtBu)4. TMS-ITC undergoes condensation with ethyl 2-benzylamino-5-methyl-3-phenylcyclopent-1-enecarboxylate to yield 1-benzyl-5-methyl-7-phenyl-2-thioxo-1,2,3,5,6,7-hexahydrocyclopentapyrimidin-4-one. It participates in ring opening reaction of N-substituted aziridines and cyclohexene oxide.

Purification Methods

The 1H NMR spectrum should have only one peak; if not purify it by repeated fractionation in an all-glass system using a 50cm (4mm internal diameter) column without packing. [Anderson J Am Chem Soc 69 3049 1947, Fehér & Blümcke Chem Ber 90 1934 1957, Neidleim & Hege Synthesis 51 1975, Beilstein 4 III 1861, 4 IV 4011.]

InChI:InChI=1/C4H9NSSi/c1-7(2,3)5-4-6/h1-3H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 540-72-7 sodium thiocyanide 
• 1147550-11-5 ammonium thiocyanate 
• 592-87-0 lead(II) thiocyanate 
• 17356-08-0 thiourea 
• 3385-94-2 hexamethyldisilathiane 
• 13125-51-4 diisothiocyanato-dimethyl-silane 
• 7677-24-9 trimethylsilyl cyanide 
• 4073-59-0 bis-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinan-2-yl)disulfide 
• 18306-95-1 O,O-diethyl S-(trimethylsilyl) phosphorodithioate 
• 87290-46-8 2-isothiocyanato-4,5-dimethyl-1,3,2-dioxaphospholane 
• 18306-29-1 bis(trimethylsilyl)sulphate 
• 333-20-0 potassium thioacyanate 
• 1072-43-1 propylene sulphide 

Downstream Products

• 1858-25-9 phosphoryl-isothiocyanate 
• 27352-07-4 CF₄N₂P₂S₂ 
• 6374-26-1 diethyl phosphorisothiocyanatidate 
• 21185-13-7 N-methylthiosemicarbazide 
• 6938-68-7 2-methyl-thiosemicarbazide 
• 4411-26-1 1-adamantylisothiocyanate 
• 39825-84-8 1-thiocyanatoadamantane 
• 100-39-0 benzyl bromide 
• 622-78-6 Benzyl isothiocyanate 
• 130837-42-2 3-Thiocyanato-adamantan-1-ol 
• 130837-41-1 3-isothiocyanatoadamantan-1-ol 
• 113815-97-7 α-methoxybenzyl isothiocyanate 
• 130473-69-7 (3aR,6aR)-1,4-Dicyclohexyl-tetrahydro-imidazo[4,5-d]imidazole-2,5-dithione 
• 130452-21-0 (3aR,6aR)-1,4-Bis-(4-methoxy-phenyl)-tetrahydro-imidazo[4,5-d]imidazole-2,5-dithione 

Relevant articles and documents

THE MOLECULAR STRUCTURE OF TRIMETHYLSILYLISOTHIOCYANATE IN THE GAS PHASE, DETERMINED BY ELECTRON DIFFRACTION

The structure of gaseous trimethylsilylisothiocyanate has been redetermined by electron diffraction.In the ra structure, the bondlengths are Si-C 186.6(3), Si-N 174.3(6), N=C 119.1(6), C=S 158.7(4) and C-H 110.0(5) pm, and the angles are NSiC 108.8(7), SiNC 158.2(10) and SiCH 108.9(8) deg.There is a small apparent deviation from linearity (ca. 4 deg) in the NCS group, but it is likely that the SiNCS skeleton is pseudolinear, as is in related molecules.

Pseudohalonium ions: [Me3Si-X-SiMe3]+ (X = CN, OCN, SCN, and NNN)

By utilizing reaction mixtures, such as Me3Si-XV[Me 3Si-X-SiMe3]+ (X = CN, OCN, SCN, and NNN), it was possible to prepare the first examples of bissilylated pseudohalonium cations in high yields. The structure and bonding of a whole series of salts containing pseudohalonium cations is discussed on the basis of experimentally observed (X-ray diffraction, Raman, and IR spectroscopy, and mass spectrometry) and theoretically obtained data. Salts containing pseudohalonium cations are only stable in the presence of weakly coordinating anions, such as the well-known tetrakis(pentafluorophenyl)borate, [B(C6Fs) 4]-.

Cyanogen formation during asymmetric cyanohydrin synthesis

During asymmetric cyanohydrin synthesis catalysed by vanadium Voxo(salen) complexes, the catalysts are reduced to vanadium IVoxo(salen) as determined by EPR spectroscopy; the reducing agent is cyanide which is oxidised to cyanogen via a non-radical mechanism.