MilliporeSigma
All Photos(1)

212849

Sigma-Aldrich

Trimethylsilyl cyanide

98%

Synonym(s):
Cyanotrimethylsilane, TMSCN
Linear Formula:
(CH3)3SiCN
CAS Number:
Molecular Weight:
99.21
Beilstein:
1737612
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
73328440442359742
Trimethylsilyl cyanide technical, ≥95% (GC)

Sigma-Aldrich

73328

Trimethylsilyl cyanide

form

liquid

form

liquid

form

liquid

form

liquid

refractive index

n20/D 1.392 (lit.)

refractive index

n20/D 1.392 (lit.)

refractive index

n20/D 1.405 (lit.)

refractive index

n20/D 1.424 (lit.)

bp

114-117 °C (lit.)

bp

114-117 °C (lit.)

bp

98-100 °C (lit.)

bp

168-169 °C (lit.), 62-64 °C/10 mmHg (lit.)

mp

8-11 °C (lit.)

mp

8-11 °C (lit.)

mp

-

mp

−26 °C (lit.)

density

0.793 g/mL at 20 °C (lit.)

density

0.793 g/mL at 20 °C (lit.)

density

0.86 g/mL at 25 °C (lit.)

density

1.225 g/mL at 25 °C (lit.)

General description

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

Application

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

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

33.8 °F

Flash Point(C)

1 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (Example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 5

1 of 5

Synthetic Communications, 36, 2483-2483 (2006)
Tetrahedron Asymmetry, 17, 2328-2328 (2006)
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)
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service