| Identification | More | [Name]
4-TRIMETHYLSILYL-3-BUTYN-2-OL | [CAS]
6999-19-5 | [Synonyms]
1-TRIMETHYLSILYLBUT-1-YNE-3-OL
(+/-) 4-TRIMETHYLSILYL-3-BUTYN-2-OL
4-TRIMETHYLSILYL-3-BUTYN-2-OL
4-TRIMETHYLSILYL-3-BUTYN-2-OL (+/-)
TIMTEC-BB SBB009027
4-(Trimethysilyl)-3-butyn-2-ol
4-TRIMETHYLSILYL-3-BUTYN-2-OL: TECH., 90%
4-Trimethylsilyl-3-butynol, tech. 90% | [Molecular Formula]
C7H14OSi | [MDL Number]
MFCD00190213 | [Molecular Weight]
142.27 | [MOL File]
6999-19-5.mol |
| Chemical Properties | Back Directory | [Boiling point ]
76 °C | [density ]
0.847 g/mL at 25 °C
| [refractive index ]
n 20/D 1.446
| [Fp ]
143 °F
| [storage temp. ]
2-8°C | [solubility ]
highly soluble in all standard organic solvents
(hexanes, toluene, CH2Cl2, EtOAc, alcohols, ethers). Partially
soluble in water. | [form ]
clear liquid | [pka]
13.78±0.20(Predicted) | [color ]
Colorless to Light orange to Yellow | [Specific Gravity]
0.846 | [Hydrolytic Sensitivity]
4: no reaction with water under neutral conditions | [BRN ]
1923632 | [CAS DataBase Reference]
6999-19-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
1993 | [WGK Germany ]
3 | [TSCA ]
No | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless liquid | [Physical properties]
bp 83–85°C (13 mmHg). | [Uses]
More recently, Mulzer has reported use of the corresponding
allenylsilane derived from 4-TMS-3-butyn-2-ol for use in the synthesis
of the C13–C18 fragment of branimycin (eq 2).
| [Preparation]
racemic 4-trimethylsilyl-3-butyn-2-ol can
be prepared by deprotonation with strong bases (BuLi, LDA,
Grignards reagents) of trimethylsilylacetylene followed
by addition to acetaldehyde.Deprotonation of 3-butyn-2-
ol followed by quenching with excess trimethylsilyl chloride
followed by concomitant hydrolysis of the trimethylsilyl ether
is generally the most straightforward route.Enzymatic reduction
of 4-TMS-3-butyn-2-one has also been used to prepare the
reagent using alcohol dehydrogenase.
Preparation of nonracemic 4-TMS-3-butyn-2-ol has been
accomplished by asymmetric addition of dimethylzinc to
acetaldehyde promoted by TADDOL or addition of a
trimethylsilylvinylsulfoxide to acetaldehyde followed by thermal
elimination of the sulfoxide.Asymmetric reduction of 4-
TMS-3-butyn-2-one using stoichiometric reducing reagents,
catalytic transfer hydrodrogenation,and enzymatic reduction
with isolated protein or whole cells afford the 4-TMS-3-butyn-
2-ol with varying degrees of enantioenrichment.Enzymatic resolution by esterification of the racemic alcohol is the method
of choice for the large-scale preparation. |
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