Trimethylsilyl cyanide

Trimethylsilyl cyanide  |  |

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Names
Preferred IUPAC name

Trimethylsilanecarbonitrile

Other names

Cyanotrimethylsilane; TMS cyanide; Trimethylsilylnitrile; Trimethylsilylcarbonitrile; Trimethylsilylformonitrile

Identifiers

CAS Number

* 7677-24-9 Y

3D model (JSmol)

* Interactive image

Abbreviations  | TMSCN
ChemSpider |

* 74110 Y

EC Number |

* 231-657-3

PubChem CID

* 82115

InChI

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

Key: LEIMLDGFXIOXMT-UHFFFAOYSA-N Y

* InChI=1/C4H9NSi/c1-6(2,3)4-5/h1-3H3

Key: LEIMLDGFXIOXMT-UHFFFAOYAM

SMILES

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

Properties

Chemical formula

| C4H9NSi
Molar mass | 99.208 g·mol−1
Density | 0.793 g/mL at 20 °C
Melting point |  8 to 11 °C (46 to 52 °F; 281 to 284 K)
Boiling point |  114 to 117 °C (237 to 243 °F; 387 to 390 K)

Solubility in water

| hydrolyzes
Solubility | organic solvents

Refractive index (nD)

| 1.392
Hazards
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H225, H300, H310, H330, H410

GHS precautionary statements

| P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P303+361+353, P304+340, P310, P320, P321, P322, P330, P361, P363
Flash point |  1 °C (34 °F; 274 K)
Related compounds

Other anions

| Trimethylsilyl chloride

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* PairSizeSet

Trimethylsilyl cyanide is the chemical compound with the formula (CH3)3SiCN. This volatile liquid consists of a cyanide group, that is CN, attached to a trimethylsilyl group. The molecule is used in organic synthesis as the equivalent of hydrogen cyanide. It is prepared by the reaction of lithium cyanide and trimethylsilyl chloride:[1][2]

LiCN + (CH3)3SiCl → (CH3)3SiCN + LiCl

## Contents

* 1 Structure
* 2 Reactions
* 3 Safety
* 4 References

## Structure

The molecule exhibits the structure of a nitrile-like compound. The compound exists in a rapid equilibrium with a small amount of the isomeric isocyanide (CH3)3SiNC.[3] By contrast, the nearly isostructural tert-butyl nitrile does not readily isomerize to tert-butyl isocyanide. The isocyanide isomer can be stabilized by complexation to metals.[4]

## Reactions

Trimethylsilyl cyanide hydrolyzes to give hydrogen cyanide and trimethylsilanol:

(CH3)3SiCN + H2O → (CH3)3SiOH + HCN

In its principal application, it adds across carbon-oxygen double bonds, for example in an aldehyde, to form a new carbon-carbon bond:[2]

RCH=O \+ (CH3)3SiC≡N → N≡C-CHR-OSi(CH3)3

The product is an O-silylated cyanohydrin.

One use of this reagent is to convert pyridine-N-oxides into 2-cyanopyridine. This transformation is best done in dichloromethane solution using dimethylcarbamoyl chloride as the activating electrophile. It is possible to use benzoyl chloride but the yields and regioselectivity of the addition of the cyano group are lower.

Acetone cyanohydrin can be used to reversibly generate the cyanide anion.[5]

(4)

## Safety

Trimethylsilyl cyanide behaves equivalently to hydrogen cyanide, a potent poison.[2] The compound can be disposed of by using a mixture of alkali hydroxide and bleach.[6]

## References

1. ↑ Livinghouse, T. (1981). "Trimethylsilyl Cyanide: Cyanosilation of p-Benzoquinone". Organic Syntheses 60: 126. doi:10.15227/orgsyn.060.0126.
2. ↑ 2.0 2.1 2.2 Groutas, William C.; Jin, Zhendong; Zhang, Heng (2011). "Cyanotrimethylsilane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc276.pub2. ISBN 978-0471936237.
3. ↑ Booth, M. R.; Frankiss, S. G. (1968). "Trimethylsilyl isocyanide". Chem. Commun. (21): 1347–1348. doi:10.1039/C19680001347.
4. ↑ Bose, Moumita; Moula, Golam; Begum, Ameerunisha; Sarkar, Sabyasachi (2018). "Synthesis and Characterization of Cyano and Isocyano Complexes of Bis(dithiolato) Molybdenum Using Me3SiCN: A Route to a Cyanide-Bridged Multimer to a Monomer". New Journal of Chemistry 42 (7): 5580–5592. doi:10.1039/C8NJ00246K.
5. ↑ Nazarov, N. ; Zav'yalov, I. J. Gen. Chem. USSR (Engl. Transl.) 1954, 24, 475 [C.A., 49, 6139f (1955)].
6. ↑ MSDS of trimethylsilyl cyanide. (PDF). Gelest. [Jun 13, 2019]

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*[CID]: Compound ID
*[H225]: Highly flammable liquid and vapour
*[H300]: Fatal if swallowed
*[H310]: Fatal in contact with skin
*[H330]: Fatal if inhaled
*[H410]: Very toxic to aquatic life with long lasting effects
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P262]: Do not get in eyes, on skin, or on clothing
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P284]: Wear respiratory protection
*[P301+310]: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
*[P302+350]: IF ON SKIN: Gently wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P320]: Specific treatment is urgent (see … on this label)
*[P321]: Specific treatment (see … on this label)
*[P322]: Specific measures (see … on this label)
*[P330]: Rinse mouth
*[P361]: Remove/Take off immediately all contaminated clothing
*[P363]: Wash contaminated clothing before reuse