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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

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.)

functional group

hydroxyl

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
MKCW6223
MKCT9541
MKCV2158
MKCT0482
MKCR9801

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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
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
Kun Liu et al.
Nucleic acids research, 48(13), 7356-7370 (2020-06-11)
To enable the optimal, biocompatible and non-destructive application of the highly useful copper (Cu+)-mediated alkyne-azide 'click' cycloaddition in water, we have isolated and characterized a 79-nucleotide DNA enzyme or DNAzyme, 'CLICK-17', that harnesses as low as sub-micromolar Cu+; or, surprisingly
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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