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Sigma-Aldrich

Trimethylsilyl cyanide

Trimethylsilyl cyanide
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98%

Synonym(s):

Cyanotrimethylsilane, TMSCN

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About This Item

Linear Formula:
(CH3)3SiCN
CAS Number:
7677-24-9
Molecular Weight:
99.21
Beilstein:
1737612
EC Number:
231-657-3
MDL number:
MFCD00001765
UNSPSC Code:
12352100
PubChem Substance ID:
24852746
NACRES:
NA.22
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Quality Level

200

Assay

98%

form

liquid

refractive index

n20/D 1.392 (lit.)

bp

114-117 °C (lit.)

mp

8-11 °C (lit.)

density

0.793 g/mL at 20 °C (lit.)

SMILES string

C[Si](C)(C)C#N

InChI

1S/C4H9NSi/c1-6(2,3)4-5/h1-3H3

InChI key

LEIMLDGFXIOXMT-UHFFFAOYSA-N

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General description

Trimethylsilyl cyanide participates in carbonyl aminomethylation via α-silyloxy nitriles[1].

Application

Trimethylsilyl cyanide was used:
  • for derivatization of complex metabolite mixtures by GC-MS[2]
  • as cyanide source in enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones[3]
  • as reagent for the cyanosilylation of aldehydes in near quantitative yield via catalysis by silylene-bridged rare earth oxide complexes[4]
  • in asymmetric cyanosilylation with chiral dinuclear Ti(IV) complexes[5]

Packaging

Packaging material contains granular sodium carbonate as a desiccant.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Flam. Liq. 2

Supplementary Hazards

EUH014,EUH029

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

33.8 °F - closed cup

Flash Point(C)

1 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4369
SDBB0809
SHBS1211
STBL1606
STBK9203

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Synthetic applications of trimethylsilyl cyanide. Efficient synthesis of. beta.-aminomethyl alcohols.
Evans DA, et al.
The Journal of Organic Chemistry, 39(7), 914-917 (1974)
Synthetic Communications, 36, 2483-2483 (2006)
Aurora Martínez-Muñoz et al.
Organic & biomolecular chemistry, 11(47), 8247-8255 (2013-10-30)
The enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones is presented. Using trimethylsilyl cyanide (TMSCN) as the cyanide source, the reaction can be efficiently catalyzed by a tert-leucine-derived bifunctional thiourea to afford the corresponding hydrazino nitriles in good to excellent yields
Tetrahedron Asymmetry, 17, 2328-2328 (2006)
Bekzod Khakimov et al.
Analytical and bioanalytical chemistry, 405(28), 9193-9205 (2013-10-05)
Reproducible and quantitative gas chromatography-mass spectrometry (GC-MS)-based metabolomics analysis of complex biological mixtures requires robust and broad-spectrum derivatization. We have evaluated derivatization of complex metabolite mixtures using trimethylsilyl cyanide (TMSCN) and the most commonly used silylation reagent N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA). For
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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