| Identification | More | [Name]
3-TRIMETHYLSILYL-2-PROPYN-1-OL | [CAS]
5272-36-6 | [Synonyms]
1-TRIMETHYLSILYLPROPARGYL ALCOHOL
3-TRIMETHYLSILANYL-PROP-2-YN-1-OL
3-TRIMETHYLSILYL-2-PROPYN-1-OL
3-TRIMETHYLSILYL-2-PROPYNE-1-OL
3-(TRIMETHYLSILYL)PROPARGYL ALCOHOL
TIMTEC-BB SBB009061
TRIMETHYLSILYLPROPARGYL ALCOHOL
2-Propyn-1-ol, 3-(trimethylsilyl)-
3-(trimethylsilyl)-2-propyn-1-o
3-Trimethylsilylpropargylalcohol3-Trimethylsilyl-2-propyn-1-ol
3-(Trimethylsilyl)propargyl alcohol, 98+% | [EINECS(EC#)]
226-094-5 | [Molecular Formula]
C6H12OSi | [MDL Number]
MFCD00002913 | [Molecular Weight]
128.24 | [MOL File]
5272-36-6.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow liquid | [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.)
| [Fp ]
152 °F
| [storage temp. ]
2-8°C
| [solubility ]
Benzene (Sparingly) | [form ]
Liquid | [pka]
13.71±0.10(Predicted) | [color ]
Clear yellow | [Specific Gravity]
0.865 | [Water Solubility ]
Not miscible with water. | [Hydrolytic Sensitivity]
4: no reaction with water under neutral conditions | [Sensitive ]
Moisture Sensitive | [BRN ]
1902505 | [InChI]
1S/C6H12OSi/c1-8(2,3)6-4-5-7/h7H,5H2,1-3H3 | [InChIKey]
ZVGCJDPEKKEYES-UHFFFAOYSA-N | [SMILES]
C[Si](C)(C)C#CCO | [CAS DataBase Reference]
5272-36-6(CAS DataBase Reference) | [NIST Chemistry Reference]
3-Trimethylsilylpropargyl alcohol(5272-36-6) | [EPA Substance Registry System]
5272-36-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
2810 | [WGK Germany ]
3
| [F ]
8-10 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29319090 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [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 |
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