4-(Trimethylsilyl)-3-butyn-2-one Chemical Properties

Melting point:

99 °C

Boiling point:

156 °C(lit.)

Density 

0.854 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.442(lit.)

Flash point:

83 °F

storage temp. 

Flammables area

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Specific Gravity

0.854

Hydrolytic Sensitivity

4: no reaction with water under neutral conditions

InChI

InChI=1S/C7H12OSi/c1-7(8)5-6-9(2,3)4/h1-4H3

InChIKey

NQEZDDPEJMKMOS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5930-98-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36-37/39

RIDADR 

UN 1224 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

29319090

Storage Class

3 - Flammable liquids

Hazard Classifications

Eye Irrit. 2
Flam. Liq. 3
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

4-(Trimethylsilyl)-3-butyn-2-one Usage And Synthesis

Chemical Properties

clear slightly yellow liquid

Uses

4-(Trimethylsilyl)-3-butyn-2-one (TMSB) has been used to investigate its asymmetric bioreduction to (S)-4-(trimethylsilyl)-3-butyn-2-ol {(S)-TMSBOL} by employing biocompatible water-immiscible ionic liquids (ILs). TMSB may be used for the synthesis of entecavir (BMS-200475).

General Description

4-(Trimethylsilyl)-3-butyn-2-one is a ketone. Its asymmetric bioreduction to enantiopure {(S)-TMSBOL in various hydrophilic ionic liquid (ILs) solvent systems has been reported.

Synthesis

Equipped with a thermometer, spherical condenser tube (the upper end of the connection of anhydrous calcium chloride drying tube and then pass into the NaOH aqueous solution) in a 100 ml three-necked bottle, according to a certain charging method, in accordance with a certain proportion of bis (trimethylsilyl) acetylene and methanol added to the reaction bottle, and constantly pass into the nitrogen to open the reaction, when the temperature rises to 60 ~ 80 ??, began to add acetyl chloride droplets, reaction of the resulting HCI from the continuous passage of nitrogen brought out by the condensation tube, in the drying tube by NaOH aqueous solution absorption, titration is complete, and then continue to reflux for a certain period of time until the reaction temperature is no longer elevated, stop the reaction, the reaction device was quickly converted to a decompression distillation extracted half an hour of the gas for the exclusion of residual trace HCI gas, and then converted to atmospheric distillation of the reaction device to collect the fractions of 185 ?? or so, that is, the final The target product 4-trimethylsilyl-3-butyn-2-one (content higher than 97%).

4-(Trimethylsilyl)-3-butyn-2-one(5930-98-3)Related Product Information

• Norgestrel
• Mesotrione
• N-Methyl-2-pyrrolidone
• 3-Methyl butynol
• 4-Methyl-2-pentanone
• METHYL-2-PYRROLIDONE
• 3-Butyn-2-one
• 1-CYCLOPROPYL-3-TRIMETHYLSILANYL-PROPYNONE
• 4-CHLORO-1-TRIMETHYLSILANYL-PENT-1-YN-3-ONE
• 1-CHLORO-4-TRIMETHYLSILANYL-BUT-3-YN-2-ONE
• 4-CHLORO-1-TRIMETHYLSILANYL-HEX-1-YN-3-ONE
• 1-PHENYL-4-TRIMETHYLSILANYL-BUT-3-YN-2-ONE
• 1-BROMO-1-PHENYL-4-TRIMETHYLSILANYL-BUT-3-YN-2-ONE
• 4-(Trimethylsilyl)-3-butyn-2-one