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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:
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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Wenqiang Tan et al.
Carbohydrate polymers, 160, 163-171 (2017-01-25)
Four novel 1,2,3-triazolium-functionalized starch derivatives were synthesized by N-alkylating the precursor starch derivatives with 1,2,3-triazole with iodomethane based on cuprous-catalyzed azide-alkyne cycloaddition (CuAAC). The detailed structural characterization was investigated by means of FTIR, UV-vis
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