| Identification | More | [Name]
(S)-(-)-3-Butyn-2-ol | [CAS]
2914-69-4 | [Synonyms]
(S)-(-)-1-BUTYN-3-OL
(S)-(-)-3-BUTYN-2-OL
(S)-3-BUTYN-2-OL
(S)-3-BUTYNE-2-OL
(S)-but-3-yn-2-ol
(S)-(-)-3-BUTYN-2-OL, 95%, 98% EE
(S)-(-)-3-Butyn-2-ol, 98% ee
(1S)-1-Methyl-2-propyne-1-ol
(2S)-3-Butyn-2-ol
(3S)-1-Butyn-3-ol | [EINECS(EC#)]
608-322-9 | [Molecular Formula]
C4H6O | [MDL Number]
MFCD00190166 | [Molecular Weight]
70.09 | [MOL File]
2914-69-4.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to yellow liquid | [Melting point ]
-22.07°C (estimate) | [alpha ]
-45 º (neat) | [Boiling point ]
108-111 °C (lit.) | [density ]
0.883 g/mL at 20 °C(lit.)
| [refractive index ]
n20/D 1.426(lit.)
| [Fp ]
78 °F
| [storage temp. ]
Poison room | [form ]
Liquid | [pka]
13.28±0.20(Predicted) | [color ]
Clear colorless to yellow | [Specific Gravity]
0.88 | [Optical Rotation]
[α]22/D 45°, neat | [Water Solubility ]
Miscible with water. | [BRN ]
4652597 | [InChI]
1S/C4H6O/c1-3-4(2)5/h1,4-5H,2H3/t4-/m0/s1 | [InChIKey]
GKPOMITUDGXOSB-BYPYZUCNSA-N | [SMILES]
C[C@H](O)C#C | [CAS DataBase Reference]
2914-69-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
F,T+ | [Risk Statements ]
R11:Highly Flammable.
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed .
R36/38:Irritating to eyes and skin .
R36/37/38:Irritating to eyes, respiratory system and skin .
R28:Very Toxic if swallowed.
R24:Toxic in contact with skin. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2929 6.1/PG 2
| [WGK Germany ]
3
| [F ]
10-23 | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29052900 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Acute Tox. 2 Dermal
Acute Tox. 2 Inhalation
Acute Tox. 2 Oral
Eye Irrit. 2
Flam. Liq. 3
Skin Irrit. 2
Skin Sens. 1 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to yellow liquid | [Uses]
(S)-(-)-3-Butyn-2-ol is used to prepare (S)-(-)-2-tert-butyldimethylsiloxybut-3-yne. It finds application in ruthenium-catalyzed polymerization to get helical polyacetylenes. | [Synthesis]
General procedure for the synthesis of (S)-(-)-3-butyn-2-ol from 3-butyn-2-ol: a substrate solution containing racemic 3-butyn-2-ol (10 g, 0.143 mol) and vinyl benzoate (41.53 g, 0.28 mol) was prepared in a total volume of 50 ml. 2.5 g of Europa lipase E2 was added to the solution ( Candida rugosa lipase). The mixed solution was placed on a shaker at 23°C (ambient temperature) for stirring the reaction. The progress of the reaction was monitored by chiral GC on a Varian CP7503 Chiralsil Dex CB column (30m x 0.32um) using helium as carrier gas at a pressure of 9.52 psi and an initial flow rate of 2 ml/min. GC conditions: initial column temperature of 50°C was held for 5 min, then ramped up at a rate of 20°C/min to 180°C and held for 2 minutes. The total run time was 13.5 min. The retention times of the components were as follows: 5.6 min corresponded to (R)-3-butyn-2-ol, 5.9 min corresponded to (S)-3-butyn-2-ol, 11.51 min corresponded to (R)-benzyl ester and 11.56 min corresponded to (S)-benzyl ester. After incubation of the reaction for 48 hours, an ee value of 96% was obtained at 75% conversion for (S)-3-butyn-2-ol. | [References]
[1] Tetrahedron: Asymmetry, 1993, vol. 4, # 7, p. 1645 - 1650
[2] Tetrahedron Asymmetry, 1998, vol. 9, # 24, p. 4429 - 4439
[3] Patent: WO2005/108346, 2005, A1. Location in patent: Page/Page column 7 |
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