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7677-24-9 molecular structure
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trimethylsilanecarbonitrile

ChemBase ID: 21464
Molecular Formular: C4H9NSi
Molecular Mass: 99.20646
Monoisotopic Mass: 99.05042583
SMILES and InChIs

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

Cite this record

CBID:21464 http://www.chembase.cn/molecule-21464.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

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 cm3
Polarizability 10.87245 Å3 Polar Surface Area 23.79 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
organic solvents expand Show data source
reacts with water expand Show data source
Apperance
clorless liquid expand Show data source
Melting Point
11-12°C expand Show data source
11-12°C expand Show data source
8 - 11°C expand Show data source
8-11 °C(lit.) expand Show data source
Boiling Point
114 - 117°C expand Show data source
114-117 °C(lit.) expand Show data source
118-119°C expand Show data source
118-119°C expand Show data source
Flash Point
1 °C expand Show data source
1°C (33.8°F) expand Show data source
1.1°C expand Show data source
1°C(33°F) expand Show data source
33.8 °F expand Show data source
Density
0.744 expand Show data source
0.744 g/ml expand Show data source
0.783 expand Show data source
0.793 g/mL at 20 °C expand Show data source
0.793 g/mL at 20 °C(lit.) expand Show data source
Refractive Index
1.3910 expand Show data source
1.392 expand Show data source
1.3920 expand Show data source
n20/D 1.391 expand Show data source
n20/D 1.392(lit.) expand Show data source
Storage Condition
Room Temperature (15-30°C), Desiccate expand Show data source
Storage Warning
KEEP COLD, TOXIC, FLAMMABLE expand Show data source
Moisture Sensitive expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Nature polluting Nature polluting (N) expand Show data source
Toxic Toxic (T) expand Show data source
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2929 expand Show data source
3273 expand Show data source
3384 expand Show data source
UN3383 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
3 expand Show data source
6.1 expand Show data source
Packing Group
1 expand Show data source
I expand Show data source
II expand Show data source
Australian Hazchem
3WE expand Show data source
Risk Statements
11-26/27/28-29 expand Show data source
11-26/27/28-29-50/53 expand Show data source
R:11-14-22 expand Show data source
R11 R26/27/28 R29 expand Show data source
Safety Statements
16-28-36/37/39-45-60-61 expand Show data source
16-36/37/39-45 expand Show data source
S:8-9-16-29-30-45 expand Show data source
S16 S36/37/39 S45 expand Show data source
EU Classification
TF1 expand Show data source
EU Hazard Identification Number
6.1A expand Show data source
Emergency Response Guidebook(ERG) Number
131 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS06 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H225-H300 +H310 + H330 expand Show data source
H225-H300-H310-H330-H400-H410 expand Show data source
GHS Precautionary statements
P210-P260-P264-P280-P284-P301 + P310 expand Show data source
P210-P301+P310-P303+P361+P353-P304+P340-P320-P330-P361-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 3384 6.1/PG 1 expand Show data source
Supplemental Hazard Statements
Contact with water liberates toxic gas. expand Show data source
Purity
≥95% (GC) expand Show data source
≥97.0% (H-NMR) expand Show data source
97% expand Show data source
98% expand Show data source
99% expand Show data source
Grade
purum expand Show data source
technical expand Show data source
Certificate of Analysis
Download expand Show data source
Linear Formula
(CH3)3SiCN expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02105685 external link
Purity: 98%
1 ml = approx. 0.74 g
Reagent for preparation of cyanohydrins.
Sigma Aldrich - 212849 external link
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 external link
包装
50, 250 mL in glass bottle
Sigma Aldrich - 92755 external link
Caution
may discolor to deep yellow on storage

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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