302481
4-Pentyn-1-ol
97%
Synonym(s):
(3-Hydroxypropyl)acetylene, 1-Hydroxy-4-pentyne, 1-Pentyn-5-ol, 5-Hydroxy-1-pentyne, Pent-4-yn-1-ol, Pent-4-yne-1-ol, Pentyne alcohol
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All Photos(2)
About This Item
Linear Formula:
HC≡CCH2CH2CH2OH
CAS Number:
Molecular Weight:
84.12
Beilstein:
1736712
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
97%
form
liquid
refractive index
n20/D 1.445 (lit.)
bp
154-155 °C (lit.)
density
0.904 g/mL at 25 °C (lit.)
SMILES string
OCCCC#C
InChI
1S/C5H8O/c1-2-3-4-5-6/h1,6H,3-5H2
InChI key
CRWVOXFUXPYTRK-UHFFFAOYSA-N
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General description
Mechanism of (THF)W(CO)5-promoted endo- and exo-cycloisomerization of 4-pentyn-1-ol was studied.
Application
4-Pentyn-1-ol was used in preparation of 3-pent-4-ynyloxy phthalonitrile. It was also used as starting reagent in stereoselective total synthesis of antimicrobial marine metabolites, ieodomycin A and B.
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
143.6 °F - closed cup
Flash Point(C)
62 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Journal of the American Chemical Society, 127(3), 944-952 (2005-01-20)
New solvent-assisted mechanistic routes were located for the (THF)W(CO)5-promoted endo- and exo-cycloisomerization of 4-pentyn-1-ol using the B3LYP/6-31G (with the LANL2DZ relativistic pseudopotential for W) theory level. A mixed model was used by explicitly including a THF molecule as a component
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The Journal of organic chemistry, 78(14), 7274-7280 (2013-06-21)
Stereoselective total synthesis of antimicrobial marine metabolites ieodomycin A and B have been accomplished starting from commercially available 4-pentyn-1-ol featuring strategic application of the Negishi reaction, Kumada coupling, and Crimmins acetate aldol. This revises the proton NMR spectra of ieodomycin
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