| Identification | More | [Name]
N-[(Trimethylsilyl)methyl]benzylamine | [CAS]
53215-95-5 | [Synonyms]
N-BENZYLAMINOMETHYLTRIMETHYLSILANE
N-(TRIMETHYLSILYLMETHYL)BENZYLAMINE
SILANE BENZYL-TMSMA
N-(TRIMETHYLSILYLMETHYL)BENZYAMINE
Benzyl(trimethylsilylmethyl)amine | [Molecular Formula]
C11H19NSi | [MDL Number]
MFCD00012192 | [Molecular Weight]
193.36 | [MOL File]
53215-95-5.mol |
| Chemical Properties | Back Directory | [Boiling point ]
89-90 °C5 mm Hg(lit.) | [density ]
0.88 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.496(lit.)
| [Fp ]
205 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Liquid | [pka]
9.29±0.20(Predicted) | [color ]
Pale yellow | [Specific Gravity]
0.88 | [Hydrolytic Sensitivity]
4: no reaction with water under neutral conditions | [InChI]
InChI=1S/C11H19NSi/c1-13(2,3)10-12-9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3 | [InChIKey]
WECLUYCAWLJMKM-UHFFFAOYSA-N | [SMILES]
C1(CNC[Si](C)(C)C)=CC=CC=C1 | [CAS DataBase Reference]
53215-95-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [TSCA ]
No | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless liquid | [Uses]
N-[(Trimethylsilyl)methyl]benzylamine may be used in chemical synthesis. | [General Description]
N-[(Trimethylsilyl)methyl]benzylamine is useful intermediate to cyanoaminosilanes which are subsequently used as azomethine ylide equivalents. | [Synthesis]
General method: Benzylamine derivatives (24.3 mmol, 37 (2.6 g); 28.0 mmol, 38 (3.4 g); 28.0 mmol, 39 (3.8 g); 11.2 mmol, 40 (1.4 g); and 11.2 mmol, 41 (2.0 g)) were dissolved in acetonitrile (120 mL), added K2CO3 (37.4 mmol, 5.2 g (for 37); 46.7 mmol, 2.5 g (for 38-39); 18.7 mmol, 2.6 g (for 40-41)) and Me3SiCH2I (18.5 mmol, 4.0 g (for 37); 38.4 mmol, 59 g (for 38-39); 9.3 mmol, 2.0 g (for 40-41)). The reaction mixture was stirred for 12 h at room temperature. After completion of the reaction, the mixture was concentrated in vacuum to give a residue. The residue was ground with CH2Cl2, dried and concentrated again under vacuum. Finally, it was purified by silica gel column chromatography (eluent ratio: EtOAc:hexane=1:8~1:15) to give the products 421 (3.2 g, 89%), 43 (3.85 g, 79%), 442 (3.3 g, 63%), 45 (1.51 g, 76%) and 46 (1.9 g, 78%), respectively. | [References]
[1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3014 - 3018
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 44, p. 10502 - 10510
[3] Tetrahedron Letters, 2017, vol. 58, # 10, p. 949 - 954
[4] Tetrahedron, 2017, vol. 73, # 44, p. 6249 - 6261 |
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