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Key Documents

519235

Sigma-Aldrich

4-Ethynylbenzyl alcohol

97%

Synonym(s):

4-Hydroxymethylphenylacetylene

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About This Item

Linear Formula:
HC≡CC6H4CH2OH
CAS Number:
Molecular Weight:
132.16
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

mp

40-44 °C (lit.)

functional group

hydroxyl

SMILES string

OCc1ccc(cc1)C#C

InChI

1S/C9H8O/c1-2-8-3-5-9(7-10)6-4-8/h1,3-6,10H,7H2

InChI key

QCZORVSTESPHCO-UHFFFAOYSA-N

Application

  • 4-Ethynylbenzyl alcohol can be used in the synthesis of platinum-acetylide dendrimers, rotaxanes and arylacetylenes.
  • It was employed in the preparation of arylalkyne-tagged sugars for the photoinduced glycosylation of cysteine-containing peptides.
  • It can also act as a precursor to synthesize fluorescent probes via Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Dendron decorated platinum (II) acetylides for optical power limiting.
Vestberg R, et al.
Macromolecules, 39(6), 2238-2246 (2006)
Catalytic ?Active-Metal? Template Synthesis of [2] Rotaxanes,[3] Rotaxanes, and Molecular Shuttles, and Some Observations on the Mechanism of the Cu (I)-Catalyzed Azide? Alkyne 1, 3-Cycloaddition.
Aucagne V, et al.
Journal of the American Chemical Society, 129(39), 11950-11963 (2007)
Susimaire P Mantoani et al.
Molecules (Basel, Switzerland), 21(2), doi:10-doi:10 (2016-02-11)
Alzheimer's disease (AD) is the most prevalent neurodegenerative disorder worldwide. Currently, the only strategy for palliative treatment of AD is to inhibit acetylcholinesterase (AChE) in order to increase the concentration of acetylcholine in the synaptic cleft. Evidence indicates that AChE
A fluorogenic `click?reaction of azidoanthracene derivatives.
Xie F, et al.
Tetrahedron, 64(13), 2906-2914 (2008)
Synthesis and conformation effects of poly (phenylacetylene) s having chiral and racemic polylactide pendants.
Zhang C, et al.
Polymer International, 61(7), 1158-1162 (2012)

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