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302015

Sigma-Aldrich

5-Hexyn-1-ol

96%

Synonym(s):

1-Hexyn-6-ol, 1-Hydroxy-5-hexyne, 5-Hexynol, 5-Hexynyl alcohol, 6-Hydroxy-1-hexyne

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About This Item

Linear Formula:
HC≡C(CH2)4OH
CAS Number:
928-90-5
Molecular Weight:
98.14
Beilstein:
1739774
MDL number:
MFCD00002980
UNSPSC Code:
12352100
PubChem Substance ID:
24858225
NACRES:
NA.22

Quality Level

100

Assay

96%

form

liquid

refractive index

n20/D 1.450 (lit.)

bp

73-75 °C/15 mmHg (lit.)

density

0.89 g/mL at 25 °C (lit.)

SMILES string

OCCCCC#C

InChI

1S/C6H10O/c1-2-3-4-5-6-7/h1,7H,3-6H2

InChI key

GOQJMMHTSOQIEI-UHFFFAOYSA-N

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Application

5-Hexyn-1-ol was used in synthesis of:
  • cinnoline-fused cyclic enediyne
  • llycopodium alkaloids, (+)-nankakurine A and (+)-nankakurine B
  • 7-benzoyloxy-3-(2-nitrophenylseleno)-1,5-cyclodecadiyne

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

158.0 °F - closed cup

Flash Point(C)

70 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ4039
MKCP8619
MKCM3941
MKCJ9999
MKCH3143

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M Michida et al.
Nucleic acids symposium series, (37)(37), 55-56 (1997-01-01)
7-Benzoyloxy-3-(2-nitrophenylseleno)-1,5-cyclodecadiyne (13) was prepared from 5-hexyn-1-ol and propargyl bromide via 10-iodo-7-(t-butyldiphenylsiloxy)-5,9-decadiynal (10). The facile cyclization of the acyclic precursor 10 would be rationalized in terms of "bulky group (TBDPSO) assisted conformational control". Oxidation of 13 by NaIO4, followed by thermal
Olga V Vinogradova et al.
The Journal of organic chemistry, 76(16), 6937-6941 (2011-07-02)
A short and efficient synthesis of cinnoline-fused cyclic enediyne is reported. Richter cyclization of o-(1,3-butadiynyl)phenyltriazene produced 3-alkynyl-4-bromocinnoline. The Sonogashira coupling of the latter with 5-hexyn-1-ol was employed for the introduction of a second acetylenic moiety. The crucial cyclization step was
Ryan A Altman et al.
The Journal of organic chemistry, 75(22), 7519-7534 (2010-10-21)
The first total syntheses of the Lycopodium alkaloids (+)-nankakurine A (2), (+)-nankakurine B (3), and the originally purported structure 1 of nankakurine A were accomplished. The syntheses of 2 and 3 feature a demanding intramolecular azomethine imine cycloaddition as the
Johanna E Grimm et al.
Journal of agricultural and food chemistry, 67(20), 5838-5846 (2019-05-06)
An aroma extract dilution analysis applied to the volatiles isolated from jackfruit ( Artocarpus heterophyllus Lam.) pulp by solvent extraction and solvent-assisted flavor evaporation resulted in the detection of 48 odorants with flavor dilution (FD) factors between 1 and ≥8192.
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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Articles

Functionalized Alkynes

Alkynes contain a highly versatile functional group that may be utilized for numerous reactions such as electrophilic additions of hydrogen, halogens, hydrogen halides, or water; metathesis; hydroboration; oxidative cleavage; C–C coupling; and cycloadditions

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