3-TRIMETHYLSILYL-2-PROPYN-1-OL

3-TRIMETHYLSILYL-2-PROPYN-1-OL Property

Melting point:

63.5-65.0 °C

Boiling point:

76 °C11 mm Hg(lit.)

Density 

0.865 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.451(lit.)

Flash point:

152 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Benzene (Sparingly)

pka

13.71±0.10(Predicted)

form 

Liquid

color 

Clear yellow

Specific Gravity

0.865

Water Solubility 

Not miscible with water.

Sensitive 

Moisture Sensitive

Hydrolytic Sensitivity

4: no reaction with water under neutral conditions

BRN 

1902505

InChIKey

ZVGCJDPEKKEYES-UHFFFAOYSA-N

CAS DataBase Reference

5272-36-6(CAS DataBase Reference)

NIST Chemistry Reference

3-Trimethylsilylpropargyl alcohol(5272-36-6)

EPA Substance Registry System

2-Propyn-1-ol, 3-(trimethylsilyl)- (5272-36-6)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-24/25-37/39-26

RIDADR 

2810

WGK Germany 

3

F 

8-10

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P309IF exposed or if you feel unwell:

P310Immediately call a POISON CENTER or doctor/physician.

3-TRIMETHYLSILYL-2-PROPYN-1-OL Chemical Properties,Usage,Production

Chemical Properties

clear yellow liquid

Uses

Trimethylsilylpropargyl alcohol is used as a reagent to synthesize Isbogrel, a Thromboxane A 2 (TXA 2) synthase inhibitor and also a TXA 2 receptor antagonist that has potential to treat asthma.

Application

3-Trimethylsilyl-2-propyn-1-ol is a colourless transparent liquid which is sensitive to light, air and moisture, and can be used as raw material for organic synthesis or reaction reagent. Alkyllithiums undergo trans addition to 3-(trimethylsilyl)-2-propyn-1-ols to yield (1-lithiovinyl)silanes. Due to unidentified side-reactions, yields do not exceed 20%.

Synthesis

Compound 5 (0.250 g, 1.17 mmol) was added dropwise to a flask containing methanol (4.0 mL) and Amberlyst-15 (0.025 g) under nitrogen protection at a reaction temperature of 0 °C. The reaction mixture was warmed to 40 °C and stirred for 8 hours. Upon completion of the reaction, the resin was removed by filtration and washed with ethyl acetate (10 mL). To the filtrate, 10% aqueous hydrochloric acid (10 mL) was added, followed by extraction of the organic layer with ethyl acetate (3 x 10 mL). The organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by column chromatography (eluent: hexane/ethyl acetate = 9:1) to afford compound 6 in 96% yield (0.143 g, 1.12 mmol).

References

[1] Tetrahedron, 1996, vol. 52, # 21, p. 7487 - 7510
[2] Journal of the Brazilian Chemical Society, 2013, vol. 24, # 12, p. 1933 - 1941
[3] Chemistry - A European Journal, 2015, vol. 21, # 27, p. 9662 - 9665
[4] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1987, p. 1077 - 1082
[5] Journal of Organic Chemistry, 1995, vol. 60, # 14, p. 4650 - 4652