TRIMETHYLSILYL ISOTHIOCYANATE Property

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.

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

Sensitive 

Moisture Sensitive

BRN 

1745262

InChIKey

XLTUPERVRFLGLJ-UHFFFAOYSA-N

CAS DataBase Reference

2290-65-5(CAS DataBase Reference)

EPA Substance Registry System

Isothiocyanatotrimethylsilane (2290-65-5)

Safety

Hazard Codes 

T

Risk 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

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

TRIMETHYLSILYL ISOTHIOCYANATE Chemical Properties,Usage,Production

Chemical Properties

clear colorless to light yellow liquid

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.

Uses

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.]