(S)-(-)-3-Butyn-2-ol Chemical Properties

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.)

Flash point:

78 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

pka

13.28±0.20(Predicted)

Specific Gravity

0.88

color 

Clear colorless to yellow

optical activity

[α]22/D 45°, neat

Water Solubility 

Miscible with water.

BRN 

4652597

InChIKey

GKPOMITUDGXOSB-BYPYZUCNSA-N

CAS DataBase Reference

2914-69-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

F,T+

Risk Statements 

11-26/27/28-36/38-36/37/38-28-24

Safety Statements 

16-26-36/37/39-45-28A

RIDADR 

UN 2929 6.1/PG 2

WGK Germany 

3

F 

10-23

HazardClass 

6.1

PackingGroup 

II

HS Code 

29052900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

(S)-(-)-3-Butyn-2-ol Usage And Synthesis

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.

Uses

Used in a ruthenium-catalyzed polymerization providing 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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