3-TRIMETHYLSILYLPROPYNAL Chemical Properties

Melting point:

195 °C

Boiling point:

52 °C

Density 

0.854 g/mL at 25 °C

refractive index 

n20/D 1.444

Flash point:

>25°C

storage temp. 

2-8°C

form 

Liquid

Specific Gravity

0.86

color 

Colorless to yellow

Sensitive 

Air & Moisture Sensitive

Hydrolytic Sensitivity

4: no reaction with water under neutral conditions

InChI

InChI=1S/C6H10OSi/c1-8(2,3)6-4-5-7/h5H,1-3H3

InChIKey

LJRWLSKYGWLYIM-UHFFFAOYSA-N

SMILES

C(=O)C#C[Si](C)(C)C

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

16-36/37/39-36/37-26

RIDADR 

1993

WGK Germany 

3

TSCA 

No

HazardClass 

3

PackingGroup 

II

HS Code 

29319090

MSDS

• Language:English Provider:ALFA

3-TRIMETHYLSILYLPROPYNAL Usage And Synthesis

Uses

3-Trimethylsilylpropynal acts as an important organic intermediate. It is used in agrochemicals, pharmaceuticals and dyestuff field. Further, it is used in the preparation of [3-(trimethylsilyl)-2-propinyliden]-malononitrile.

Synthesis

Steps for the synthesis of 3-trimethylsilylpropynal: 1. A solution of trimethylsilylacetylene (5.0 mL, 36.10 mmol) in THF (25.0 mL) was added dropwise to a solution of EtMgBr in THF (1 M, 44.0 mL, 44.0 mmol) under nitrogen protection, and the reaction temperature was maintained at 10-150°C. 2. After the dropwise addition, the reaction mixture was stirred at room temperature for 1 hour. 3. A solution of Et2O (20.0 mL) in DMF (10.0 mL, 123.0 mmol) was slowly added to the reaction system at -25 °C, and the addition time was controlled to be within 30 min. 4. The resulting white suspension was gradually warmed to room temperature and stirring was continued for 1 hour. 5. The reaction mixture was heated to 30 °C and maintained for 15 minutes. 6. The reaction solution was cooled to 0 °C and poured into 5% H2SO4 solution. 7. The aqueous layer was separated and extracted three times with Et2O. 8. Combine the organic layers, wash with saturated aqueous NH4Cl solution and dry with anhydrous Na2SO4. 9. Concentrate under pressure to remove the solvent and obtain the crude product. 10. purification of the crude product by ball-to-ball distillation (20 mbar, room temperature) afforded 3-trimethylsilylpropynal (2.255 g, 49% yield). Product characterization data: 1H NMR: δ 9.15 (s, 1H), 0.25 (s, 9H). 13C NMR: δ 176.7, 103.0, 102.3, 0.88.

References

[1] Tetrahedron Letters, 1995, vol. 36, # 3, p. 401 - 404
[2] Angewandte Chemie - International Edition, 2008, vol. 47, # 6, p. 1130 - 1133
[3] Tetrahedron, 2002, vol. 58, # 12, p. 2415 - 2422
[4] Arkivoc, 2012, vol. 2012, # 7, p. 253 - 273
[5] Patent: WO2009/141781, 2009, A1. Location in patent: Page/Page column 18

3-TRIMETHYLSILYLPROPYNAL(2975-46-4)Related Product Information

• (TERT-BUTYLDIMETHYLSILYLOXY)ACETALDEHYDE
• Propyne
• 3-(TRIMETHYLSILYL)PROPIOLIC ACID
• METHYL 3-(TRIMETHYLSILYL)PROPIOLATE
• 4-(Trimethylsilyl)-3-butyn-2-one
• 3-TRIMETHYLSILYLPROPYNAL
• 1-CHLORO-4-TRIMETHYLSILANYL-BUT-3-YN-2-ONE
• ETHYL 3-(TRIMETHYLSILYL)PROPIOLATE
• TRIMETHYLSILYL(TRIMETHYLSILYL)PROPYNOATE
• 3-(Triethylsilyl)-2-propynal
• PROPYNAL
• 1-PHENYL-4-TRIMETHYLSILANYL-BUT-3-YN-2-ONE
• 3-TERT-BUTYLDIMETHYLSILYLPROPYNAL
• 1-BROMO-1-PHENYL-4-TRIMETHYLSILANYL-BUT-3-YN-2-ONE
• 4-CHLORO-1-TRIMETHYLSILANYL-HEX-1-YN-3-ONE
• 1-CYCLOPROPYL-3-TRIMETHYLSILANYL-PROPYNONE
• 4-CHLORO-1-TRIMETHYLSILANYL-PENT-1-YN-3-ONE