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302481

Sigma-Aldrich

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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About This Item

Linear Formula:
HC≡CCH2CH2CH2OH
CAS Number:
5390-04-5
Molecular Weight:
84.12
Beilstein/REAXYS Number:
1736712
EC Number:
226-383-6
MDL number:
MFCD00002974
UNSPSC Code:
12352100
PubChem Substance ID:
24858256
NACRES:
NA.22

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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

143.6 °F - closed cup

flash_point_c

62 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Tomás Sordo et al.
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
Sayantan Das et al.
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
Zeliha Kanat et al.
Dalton transactions (Cambridge, England : 2003), 43(23), 8654-8663 (2014-04-26)
In order to obtain nonperipherally tetra terminal alkynyl substituted phthalocyanines (Pcs), new 3-pent-4-ynyloxy phthalonitrile (3) was prepared by the nucleophilic displacement reaction of 3-nitrophthalonitrile (1) and 4-pentyn-1-ol (2) and then cyclotetramerization was attained in the presence of zinc acetate, cobalt
André S de Oliveira et al.
PloS one, 14(9), e0223017-e0223017 (2019-09-27)
The West Nile Virus (WNV) NS2B-NS3 protease is an attractive target for the development of therapeutics against this arboviral pathogen. In the present investigation, the screening of a small library of fifty-eight synthetic compounds against the NS2-NB3 protease of WNV
Yuan Wang et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(24), 12094-12102 (2019-05-31)
As the most common RNA cap in eukaryotes, the 7-methylguanosine (m7G) cap impacts nearly all processes that a messenger RNA undergoes, such as splicing, polyadenylation, nuclear export, translation, and degradation. The metabolite and redox agent, nicotinamide adenine diphosphate (NAD+), can
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