N-[(Trimethylsilyl)methyl]benzylamine Chemical Properties

Boiling point:

89-90 °C5 mm Hg(lit.)

Density 

0.88 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.496(lit.)

Flash point:

205 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

pka

9.29±0.20(Predicted)

Specific Gravity

0.88

color 

Pale yellow

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

TSCA 

No

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

N-[(Trimethylsilyl)methyl]benzylamine Usage And Synthesis

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

N-[(Trimethylsilyl)methyl]benzylamine(53215-95-5)Related Product Information

• 4-Fluorobenzylamine
• Methylparaben
• Kresoxim-methyl
• DL-ALPHA-METHYLBENZYLAMINE
• Methyl acrylate
• Phenoxybenzamine hydrochloride
• Methyl acetate
• N-(Trimethylsilyl)acetamide
• METHYL THIOPHENE-2-CARBOXYLATE
• Bensulfuron methyl
• N-(Trimethylsilyl)imidazole
• Trimethoprim
• Trimethylsilylacetylene
• Thiophanate-methyl
• Methyl
• (S)-(-)-N-METHOXYMETHYL-N-(TRIMETHYLSILYL)METHYL-1-PHENYLETHYLAMINE
• N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
• Methyl bromide