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464821

Sigma-Aldrich

(R)-(+)-3-Butyn-2-ol

98%

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About This Item

Linear Formula:
HC≡CCH(OH)CH3
CAS Number:
42969-65-3
Molecular Weight:
70.09
MDL number:
MFCD00211237
UNSPSC Code:
12352003
PubChem Substance ID:
24870225
NACRES:
NA.22

assay

98%

optical activity

[α]22/D +45°, neat

refractive index

n20/D 1.426 (lit.)

bp

108-111 °C (lit.)

density

0.89 g/mL at 25 °C (lit.)

SMILES string

C[C@@H](O)C#C

InChI

1S/C4H6O/c1-3-4(2)5/h1,4-5H,2H3/t4-/m1/s1

InChI key

GKPOMITUDGXOSB-SCSAIBSYSA-N

Application

(R)-(+)-3-Butyn-2-ol may be used as a starting material in the multi-step synthesis of (R)-benzyl 4-hydroxyl-2-pentynoate.
Propargylic alcohols are important starting materials for new classes of second generation 5-lipoxygenase inhibitors.
Used in a ruthenium-catalyzed polymerization providing helical polyacetylenes.

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

78.8 °F - closed cup

flash_point_c

26 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Improved large-scale synthesis of (R)-benzyl 4-hydroxyl-2-pentynoate from (R)-3-butyn-2-ol.
Fu X, et al.
Organic Process Research & Development, 6(3), 308-310 (2002)
Ku, Y.-Y. et al.
Tetrahedron Letters, 36, 2733-2733 (1995)
Bell, R.L. et al.
Lipid Mediators, 6, 529-529 (1993)
Macromolecules, 40, 1864-1864 (2007)

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