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230766

Sigma-Aldrich

(Trimethylsilyl)isothiocyanate

99%

Synonyma:

Isothiocyanatotrimethylsilane

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About This Item

Lineární vzorec:
(CH3)3SiNCS
Číslo CAS:
2290-65-5
Molekulová hmotnost:
131.27
Beilstein/REAXYS Number:
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.

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_germany

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

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Osvědčení o analýze (COA)

Lot/Batch Number
0000397752
0000397772
0000374321
0000374321
0000397752

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Ethoxycarbonyl isothiocyanate 98%

Sigma-Aldrich

196126

Ethoxycarbonyl isothiocyanate

Benzoyl isothiocyanate 98%

Sigma-Aldrich

261653

Benzoyl isothiocyanate

Thiophosphoryl chloride 98%

Sigma-Aldrich

224294

Thiophosphoryl chloride

Hexamethylene diisocyanate puriss., ≥99.0% (GC)

Sigma-Aldrich

52649

Hexamethylene diisocyanate

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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