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230766

Sigma-Aldrich

(Trimethylsilyl)isothiocyanate

99%

Sinonimo/i:

Isothiocyanatotrimethylsilane

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About This Item

Formula condensata:
(CH3)3SiNCS
Numero CAS:
2290-65-5
Peso molecolare:
131.27
Beilstein:
1745262
Numero CE:
218-929-7
Numero MDL:
MFCD00004797
Codice UNSPSC:
12352100
ID PubChem:
24853836
NACRES:
NA.22

Densità del vapore

>1 (vs air)

Saggio

99%

Stato

liquid

Indice di rifrazione

n20/D 1.482 (lit.)

P. ebollizione

143 °C (lit.)

Punto di fusione

−32.8 °C (lit.)

Densità

0.931 g/mL at 25 °C (lit.)

Temperatura di conservazione

2-8°C

Stringa SMILE

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

InChI

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

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Descrizione generale

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.

Applicazioni

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

Avvertenze

Danger

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

84.2 °F - closed cup

Punto d’infiammabilità (°C)

29 °C - closed cup

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
BGBC2281V
BGBB8307
BGBB3052
1442504
10298PJ

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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

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
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-
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
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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