3-BROMO-1-(TRIMETHYLSILYL)-1-PROPYNE Chemical Properties

Melting point:

<0°C

Boiling point:

44-45 °C2 mm Hg(lit.)

Density 

1.17 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.483(lit.)

Flash point:

145 °F

storage temp. 

2-8°C

solubility 

Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Oil

color 

Colourless to Pale Yellow

Specific Gravity

1.351

Water Solubility 

Immiscible with water.

Hydrolytic Sensitivity

4: no reaction with water under neutral conditions

BRN 

2037650

Stability:

Hygroscopic

InChIKey

GAPRPFRDVCCCHR-UHFFFAOYSA-N

CAS DataBase Reference

38002-45-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-28-36/37/39

RIDADR 

UN 3334

WGK Germany 

3

F 

8-9-19

TSCA 

No

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

3-BROMO-1-(TRIMETHYLSILYL)-1-PROPYNE Usage And Synthesis

Chemical Properties

Clear colorless to pale yellow liquid

Uses

3-Bromo-1-(trimethylsilyl)-1-propyne may be used in the preparation of tetrahydroisoquinoline-3-carboxylic acid derivatives. It may be used as reagent for the alkylation of dianion of β-keto esters at γ-carbon. It may be employed in the preparation of terminal conjugated enynes and allenic alcohols.

General Description

3-Bromo-1-(trimethylsilyl)-1-propyne is reported as a propargylating agent. Selective reaction of 3-bromo-1-(trimethylsilyl)-1-propyne with α-keto ester using indium metal has been studied.

Synthesis

The general procedure for the synthesis of 3-bromo-1-trimethylsilyl-1-propyne from trimethylsilylpropargyl alcohol was as follows: To a solution of anhydrous dichloromethane (46.0 mL) containing triphenylphosphine (9.735 g, 37.11 mmol) under nitrogen atmosphere, bromine (5.438 g, 34.03 mmol) was slowly added at 0 °C. After 30 min of reaction, when the color of the solution changed from orange to white, trimethylsilylpropynol (3.960 g, 30.93 mmol) was slowly added. The reaction mixture was continued to be stirred for 1 h, followed by washing with water (3 × 30 mL) and 10% aqueous hydrochloric acid (2 × 20 mL) sequentially. The aqueous layer was extracted with ethyl acetate (3 x 20 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using hexane as eluent to afford 3-bromo-1-trimethylsilyl-1-propyne in 70% yield (4.125 g, 21.6 mmol).

References

[1] Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8122 - 8126
[2] Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13692 - 13696
[3] Tetrahedron, 1996, vol. 52, # 35, p. 11601 - 11624
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 6127 - 6130
[5] Bulletin de la Societe Chimique de France, 1993, vol. 130, # 2, p. 154 - 159

3-BROMO-1-(TRIMETHYLSILYL)-1-PROPYNE(38002-45-8)Related Product Information

• Propargyl bromide
• 1-TRIMETHYLSILYLMETHANOL
• 4-PHENYL-3-BUTYN-2-ONE
• Propyne
• 1-(Trimethylsilyl)-1-propyne
• 3-BROMO-1-(TRIMETHYLSILYL)-1-PROPYNE
• 3-BROMO-1-(TRIETHYLSILYL)-1-PROPYNE
• 3-BROMO-1-(TRIISOPROPYLSILYL)-1-PROPYNE
• 3-BROMO-1-(TERT-BUTYLDIMETHYLSILYL)-1-PROPYNE