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Merck
모든 사진(2)

주요 문서

230766

Sigma-Aldrich

(Trimethylsilyl)isothiocyanate

99%

동의어(들):

Isothiocyanatotrimethylsilane

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About This Item

Linear Formula:
(CH3)3SiNCS
CAS Number:
Molecular Weight:
131.27
Beilstein:
1745262
EC Number:
MDL number:
UNSPSC 코드:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

>1 (vs air)

분석

99%

형태

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.)

저장 온도

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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일반 설명

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.

애플리케이션

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

픽토그램

FlameSkull and crossbonesHealth hazard

신호어

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

표적 기관

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

개인 보호 장비

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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문서 라이브러리 방문

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)
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

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