230766
(Trimethylsilyl)isothiocyanate
99%
Synonym(s):
Isothiocyanatotrimethylsilane
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About This Item
Linear Formula:
(CH3)3SiNCS
CAS Number:
Molecular Weight:
131.27
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
218-929-7
Beilstein/REAXYS Number:
1745262
MDL number:
Assay:
99%
Form:
liquid
vapor density
>1 (vs air)
Quality Level
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
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.
signalword
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
3 - Flammable liquids
wgk
WGK 3
flash_point_f
84.2 °F - closed cup
flash_point_c
29 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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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)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 230766-10G | 04061838782922 |
| 230766-50G | 04061838782939 |