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

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

CAS No:
2914-69-4
Formula:
C4H6O
Chemical Name:
3-Butyn-2-ol, (2S)-
Synonyms:
3-Butyn-2-ol,(2S)-;3-Butyn-2-ol,(-)-;3-Butyn-2-ol,(S)-;(S)-(-)-1-Butyn-3-ol;(-)-3-Butyn-2-ol;(S)-3-Butyn-2-ol;(S)-(-)-3-Butyn-2-ol;(S)-1-Butyn-3-ol;(2S)-But-3-yn-2-ol;(2S)-3-Butyn-2-ol;(2S)-But-3-yn-2-ol
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

clear colorless to yellow liquid

3-Butyn-2-ol, (2S)- Basic Attributes

Molecular Weight：

70.09

Exact Mass：

70.09

HScode：

2905290000

Characteristics

PSA：

20.2

XLogP3：

0.1

Appearance：

clear colorless to yellow liquid

Density：

0.9±0.1 g/cm3

Melting Point：

-22.07°C (estimate)

Boiling Point：

104°C at 760 mmHg

Flash Point：

25.6±0.0 °C

Refractive Index：

1.435

Water Solubility：

Miscible with water.

Storage Conditions：

Poison room

Vapor Pressure：

17.3mmHg at 25°C

Safety Information

Packing level：

Ⅱ

Hazard category：

6.1

Transport codes：

2929

wgk germany：

hazard class code：

6.1,3

safety instructions：

S16-S28-S45

Marks：

F:Flammable

Precautionary statement(s)：

P260-P264-P280-P284-P301 + P310-P302 + P350

Hazard Statements：

H226-H300-H310-H315-H317-H319-H330

3-Butyn-2-ol, (2S)- Use and Manufacturing

Enzymic Resolution of but-3-yn-2-ol A substrate solution is prepared containing racemic but-3-yn-2-ol (10g, 0.143 mol) and vinyl benzoate (41.53g, 0.28 mol). The total volume is 50ml. To the solution is added 2.5g Europa lipase E2 (Candida rugosa lipase). The solution is mixed by agitation on a shaker at 23°C (ambient temp). The reaction is monitored by chiral GC on a Varian CP7503 Chiralsil Dex CB column, 30m x 0.32um, helium carrier gas at 9.52psi and initial flow of 2ml/min. Initial oven temp 50°C for 5 min then 20°C/min to 180°C and hold for 2 min. Run time 13.5 min. Retention times 5.6min (R 3-butyn-2-ol), 5.9 min (S 3-butyn-2- ol), 11.51 min (R Benzyl ester) and 11.56 min (S Benzyl ester). After 48h incubation, (S) -3-butyn-2-ol of 96percent ee was obtained at 75percent conversion.General procedure: Enantioselectivity of PHL for Transesterication of Sec-Alcohols. The reaction mixture was prepared by mixing arac-alcohol (3a–h, 0.1 mmol), vinyl butyrate (39 μL, 0.3 mmol), and immobilized PHL (20 mg) in t-butylmethyl ether (MTBE, 1 mL). The reaction mixture wasshaken at 200 rpm. A little amount of the reaction mixture(200 μL) was retrieved and dissolved in MTBE (1 mL).After centrifugation of the diluted reaction mixture toremove the immobilized PHL, the clear solution was ana-lyzed by a GC (Agilent 6890N; Agilent Technologies, Seoul, Korea) equipped with a chiral capillary column(Cyclosil-B 30 m 0.25 mm). The GC analysis conditionfor the reaction with 3e: initial column temperature 80Cfor 5 min, ramp up to 120C at a rate of 2.5C/min, andthen held at 120C for 15 min.

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