trimethylsilanecarbonitrile

• ChemBase ID: 21464
• Molecular Formular: C4H9NSi
• Molecular Mass: 99.20646
• Monoisotopic Mass: 99.05042583
• SMILES: C[Si](C)(C)C#N
• Canonical SMILES: N#C[Si](C)(C)C
• InChI: InChI=1S/C4H9NSi/c1-6(2,3)4-5/h1-3H3
• InChIKey: LEIMLDGFXIOXMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trimethylsilanecarbonitrile
• IUPAC Traditional name: trimethylsilyl cyanide
• Synonyms: Trimethyl silane cyanide; Trimethylsilyl cyanide; Trimethylsilyl cyanide; Cyanotrimethylsilane; TMSCN; TMS cyanide; Trimethylsilylnitrile; Trimethylsilanecarbonitrile' Trimethylsilylcarbonitrile; TriMethylsilylcyanide; 氰化三甲基硅烷; 氰化三甲基硅烷; 三甲基氰硅烷

Database IDs

• CAS Number: 7677-24-9
• EC Number: 231-657-3
• MDL Number: MFCD00001765
• Beilstein Number: 1737612
• PubChem SID: 24889714; 160984771; 24886541; 24852746
• PubChem CID: 82115
• Chemspider ID: 74110
• Wikipedia Title: Trimethylsilyl_cyanide

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.9191
• LogD (pH = 7.4): 1.9191
• Log P: 1.9191
• Molar Refractivity: 23.3029 cm^3
• Polarizability: 10.87245 Å^3
• Polar Surface Area: 23.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: organic solvents; reacts with water
• Apperance: clorless liquid
• Melting Point: 11-12°C; 11-12°C; 8 - 11°C; 8-11 °C(lit.)
• Boiling Point: 114 - 117°C; 114-117 °C(lit.); 118-119°C; 118-119°C
• Flash Point: 1 °C; 1°C (33.8°F); 1.1°C; 1°C(33°F); 33.8 °F
• Density: 0.744; 0.744 g/ml; 0.783; 0.793 g/mL at 20 °C; 0.793 g/mL at 20 °C(lit.)
• Refractive Index: 1.3910; 1.392; 1.3920; n20/D 1.391; n20/D 1.392(lit.)

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: KEEP COLD, TOXIC, FLAMMABLE; Moisture Sensitive
• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T); Highly toxic (T+)
• UN Number: 2929; 3273; 3384; UN3383
• German water hazard class: 3
• Hazard Class: 3; 6.1
• Packing Group: 1; I; II
• Australian Hazchem: 3WE
• Risk Statements: 11-26/27/28-29; 11-26/27/28-29-50/53; R:11-14-22; R11 R26/27/28 R29
• Safety Statements: 16-28-36/37/39-45-60-61; 16-36/37/39-45; S:8-9-16-29-30-45; S16 S36/37/39 S45
• EU Classification: TF1
• EU Hazard Identification Number: 6.1A
• Emergency Response Guidebook(ERG) Number: 131
• TSCA Listed: false; 是
• GHS Pictograms: GHS02; GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H300 +H310 + H330; H225-H300-H310-H330-H400-H410
• GHS Precautionary statements: P210-P260-P264-P280-P284-P301 + P310; P210-P301+P310-P303+P361+P353-P304+P340-P320-P330-P361-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3384 6.1/PG 1
• Supplemental Hazard Statements: Contact with water liberates toxic gas.

Product Information

• Purity: ≥95% (GC); ≥97.0% (H-NMR); 97%; 98%; 99%
• Grade: purum; technical
• Linear Formula: (CH3)3SiCN

DETAILS

MP Biomedicals - 02105685

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

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

Sigma Aldrich - 73328

包装
50, 250 mL in glass bottle

Sigma Aldrich - 92755

Caution
may discolor to deep yellow on storage

REFERENCES

• Reagent for the formation of O-TMS cyanohydrins from carbonyl compounds.
• 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 examples of transformations of ketone TMS cyanohydrins, see: Chem. Pharm. Bull., 43, 1294 (1995).
• For use in asymmetric Strecker synthesis of chiral amino acids, see: Tetrahedron Lett., 29, 4397 (1988).
• 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).
• For a brief survey of uses of this reagent in synthesis, see: Synlett, 1625 (2007).