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

(S)-(-)-3-Butyn-2-ol Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

(S)-(-)-3-Butyn-2-ol Chemical Properties,Usage,Production

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