TRIMETHYLSILYL ISOTHIOCYANATE Chemical Properties

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 Information

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

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

TRIMETHYLSILYL ISOTHIOCYANATE Usage And Synthesis

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.]

TRIMETHYLSILYL ISOTHIOCYANATE(2290-65-5)Related Product Information

• 4-(1H)INDAZOLE CARBOXYLIC ACID METHYL ESTER
• Ethyl isonicotinate
• Isothiazolinones
• Benzyl isocyanate
• Ethoxycarbonyl Isothiocyanate
• Benzyl thiocyanate
• Trimethoxy(pentamethylcyclopentadienyl) titanium(IV)
• 3-FLUOROPHENYL ISOCYANATE
• 4-Fluorophenyl isocyanate
• Ethyl isocyanoacetate
• Isopropyl isothiocyanate
• 2-ETHOXYPHENYL ISOCYANATE
• Isobutyl isocyanate
• TRIMETHYLSILYL ISOCYANATE
• triethyl(3-isocyanatopropyl)silane
• TRIMETHYLSILYL ISOTHIOCYANATE
• isothiocyanic acid