CAS 7677-24-9|trimethylsilanecarbonitrile|Trimethylsilyl cyanide|trimethylsilyl cyanide|Trimethylsilylnitrile|TMS cyanide|Trimethylsilanecarbonitrile' Trimethylsilylcarbonitrile|Cyanotrimethylsilane...

General Information

Structure

Molecular Formula

C₄H₉NSi

Molecular Mass

99.20646

Exact Mass

99.05042583

Charge

InChI

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

InChIKey

LEIMLDGFXIOXMT-UHFFFAOYSA-N

Canonic Smiles

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

Isomeric Smiles

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

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

1.9191

LogD (pH = 7.4)

1.9191

Log P

1.9191

Molar Refractivity

23.3029

Polarizability

10.87245

Polar Surface Area

23.79

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

trimethylsilanecarbonitrile

Synonyms

Trimethylsilyl cyanideTrimethylsilylnitrileTMS cyanideTrimethylsilanecarbonitrile' TrimethylsilylcarbonitrileCyanotrimethylsilaneTMSCN氰化三甲基硅烷三甲基氰硅烷Trimethylsilyl cyanide氰化三甲基硅烷TriMethylsilylcyanideTrimethyl silane cyanide

IUPAC Traditional name

trimethylsilyl cyanide

Names and Identifiers

Registration numbers

Beilstein Number

1737612

PubChem SID

248865412488971424852746160984771

CAS Number

MDL Number

EC Number

PubChem CID

Wikipedia Title

Trimethylsilyl_cyanide

Chemspider ID

74110

Registration numbers

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

02105685

Purity: 98%
1 ml = approx. 0.74 g
Reagent for preparation of cyanohydrins.

Wikipedia

Trimethylsilyl_cyanide

Sigma Aldrich

212849

Application
Reacts with aldehydes and ketones to give cyanohydrin-TMS ethers which can be reduced to β-aminoethyl alcohols.
Reagent for the cyanosilylation of aldehydes in near quantitative yield via catalysis by silylene-bridged rare earth oxide complexes. Asymmetric cyanosilylation with chiral dinuclear Ti(IV) complexes.
Packaging
25 g in Sure/Seal™
5 g in glass bottle

73328

包装
50, 250 mL in glass bottle

92755

Caution
may discolor to deep yellow on storage

Molecule Details

References

PubChem Literature

From Data Sources

• Reagent for the formation of O-TMS cyanohydrins from carbonyl compounds.

• Tertiary alkyl halides normally undergo elimination when treated with alkali cyanides, but can be converted to the corresponding nitriles by reaction with TMSCN in the presence of SnCl₄: Angew. Chem. Int. Ed., 20, 1017 (1981).

• Reacts with epoxides in the presence of ZnI₂ to give trans-ɑ-siloxy isocyanides, which can be readily hydrolyzed to the hydroxy isocyanides: J. Am. Chem. Soc., 104, 5849 (1982); Org. Synth. Coll., 7, 294 (1990). In the presence of Ag salts (AgClO₄, AgBF₄ or AgOTf), alkenes can be converted to isocyanides in Markovnikov fashion: Synlett, 288 (1999).

• The ZnI₂-catalyzed procedure allows cyanohydrins of unreactive ketones to be prepared in good yield, avoiding the unfavourable equilibria often encountered with the classical alkali cyanide method. For details and list of examples, see: Org. Synth. Coll., 7, 20 (1990). Other catalysts including Et₃N or Bu₃P are also effective: Chem. Lett., 537, 541 (1991). For catalysis by Methyl triphenylphosphonium iodide, A15644, see: Tetrahedron Lett., 44, 6157 (2003). In the absence of a catalyst, aldehydes have been found to give good yields of the TMS cyanohydrin, but reaction with ketones is very slow: J. Chem. Soc., Perkin 1, 2383 (1995). For use of Tetracyanoethylene, A13945, as a c-acid catalyst for both aldehydes and ketones, see: J. Chem. Soc., Perkin 1, 2155 (1995). Under the same conditions, dimethyl acetals give O-methyl cyanohydrins.

• For use in asymmetric Strecker synthesis of chiral amino acids, see: Tetrahedron Lett., 29, 4397 (1988).

• For a brief survey of uses of this reagent in synthesis, see: Synlett, 1625 (2007).

• For examples of transformations of ketone TMS cyanohydrins, see: Chem. Pharm. Bull., 43, 1294 (1995).

References

Bioactivity

PubChem BioAssay

Bioactivity