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Sigma-Aldrich

(Trimethylsilyl)isothiocyanate

99%

Synonym(s):

Isothiocyanatotrimethylsilane

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About This Item

Linear Formula:
(CH3)3SiNCS
CAS Number:
2290-65-5
Molecular Weight:
131.27
Beilstein:
1745262
EC Number:
218-929-7
MDL number:
MFCD00004797
UNSPSC Code:
12352100
PubChem Substance ID:
24853836
NACRES:
NA.22

vapor density

>1 (vs air)

Assay

99%

form

liquid

refractive index

n20/D 1.482 (lit.)

bp

143 °C (lit.)

mp

−32.8 °C (lit.)

density

0.931 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C[Si](C)(C)N=C=S

InChI

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

InChI key

XLTUPERVRFLGLJ-UHFFFAOYSA-N

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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.

Application

Trimethylsilyl isothiocyanate was used as derivatizing reagent during the synthesis of amino acid thiohydantoins.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

84.2 °F - closed cup

Flash Point(C)

29 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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B Mo et al.
Analytical biochemistry, 249(2), 207-211 (1997-07-01)
A novel and efficient method to prepare amino acid thiohydantoins, which are required as reference standards for development of C-terminal protein sequencing, is reported. Amino acid thiohydantoins were prepared using a straightforward method involving reaction of 20 free amino acids
Noncatalyzed Addition of Trimethylsilyl Isothiocyanate to Aziridines and Cyclohexene Oxide.
Prusinowska N and Gawronski J.
Synthetic Communications, 39(15), 2795-2803 (2009)
J M Bailey et al.
Biochemistry, 29(12), 3145-3156 (1990-03-27)
Proteins and peptides can be sequenced from the carboxy terminus with isothiocyanate reagents to produce amino acid thiohydantoin derivatives. Previous studies in our laboratory indicated that the use of trimethylsilyl isothiocyanate (TMS-ITC) as a coupling reagent significantly improved the yields
Frans D Therkelsen et al.
Organic & biomolecular chemistry, 1(16), 2908-2918 (2003-09-13)
Condensation of 3-(3,5-dimethylphenyl)-2-oxocyclopentanecarboxamide (11) with oxalyl chloride and condensation of ethyl 2-benzylamino-5-methyl-3-phenylcyclopent-1-enecarboxylate (17a) with trimethylsilyl isothiocyanate gave 7-(3,5-dimethylphenyl)-6,7-dihydro-5H-cyclopenta[e][1,3]oxazine-2,4-dione (12) and 1-benzyl-5-methyl-7-phenyl-2-thioxo-1,2,3,5,6,7- hexahydrocyclopentapyrimidin-4-one (18a), respectively. Acid catalyzed ring-closure of 6-(4-methyl-1-phenylpent-3-enyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (26) and radical mediated ring-closure of 1,3-bis(benzyloxymethyl)-5-bromo-6-(1-phenylbut-3-enyl)-1H-pyrimidine-2,4- dione (32a) gave 5,5-dimethyl-8-phenyl-5,6,7,8-tetrahydro-1H-quinazoline-2,4-
D H Hawke et al.
Analytical biochemistry, 166(2), 298-307 (1987-11-01)
A reinvestigation of the isothiocyanate-based chemistry for cyclic degradations of peptides and proteins revealed that the reagent trimethylsilylisothiocyanate (TMS-ITC) gives superior results in terms of coupling efficiency and lack of complicating side reactions. Acetic anhydride (10 min at various temperatures)
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