TRIMETHYLSILYL ISOTHIOCYANATE

Synonym(s):Isothiocyanatotrimethylsilane

CAS NO.：2290-65-5
Empirical Formula: C4H9NSSi
Molecular Weight: 131.27
MDL number: MFCD00004797
EINECS: 218-929-7
SAFETY DATA SHEET (SDS)
Update Date: 2025-06-26 21:45:57

TRIMETHYLSILYL ISOTHIOCYANATE Structural

What is TRIMETHYLSILYL ISOTHIOCYANATE?

Chemical properties

clear colorless to light yellow liquid

The Uses of TRIMETHYLSILYL ISOTHIOCYANATE

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.

The Uses of TRIMETHYLSILYL ISOTHIOCYANATE

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.]

Properties of TRIMETHYLSILYL ISOTHIOCYANATE

Melting point:	−32.8 °C(lit.)
Boiling point:	143 °C(lit.)
Density	0.931 g/mL at 25 °C(lit.)
vapor density	>1 (vs air)
refractive index	n20/D 1.482(lit.)
Flash point:	95 °F
storage temp.	2-8°C
form	liquid
Specific Gravity	0.931
Water Solubility	Reacts with water.
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	8: reacts rapidly with moisture, water, protic solvents
BRN	1745262
CAS DataBase Reference	2290-65-5(CAS DataBase Reference)
EPA Substance Registry System	Isothiocyanatotrimethylsilane (2290-65-5)

Safety information for TRIMETHYLSILYL ISOTHIOCYANATE

Signal word	Danger
Pictogram(s)	Flame Flammables GHS02 Skull and Crossbones Acute Toxicity GHS06 Health Hazard GHS08
GHS Hazard Statements	H226:Flammable liquids H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H334:Sensitisation, respiratory H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.