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519235

Sigma-Aldrich

4-Ethynylbenzyl alcohol

97%

Synonym(s):

4-Hydroxymethylphenylacetylene

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About This Item

Linear Formula:
HC≡CC6H4CH2OH
CAS Number:
10602-04-7
Molecular Weight:
132.16
MDL number:
MFCD05664205
UNSPSC Code:
12352100
PubChem Substance ID:
24874070
NACRES:
NA.22

Assay

97%

mp

40-44 °C (lit.)

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
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

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

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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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)
Dendron decorated platinum (II) acetylides for optical power limiting.
Vestberg R, et al.
Macromolecules, 39(6), 2238-2246 (2006)
Synthesis and Optical Properties of a Polyacetylene with Hydroxy Funtional Groups: Poly (4-ethynylbenzyl Alcohol).
Gal YS, et al.
Mol. Cryst. Liq. Cryst., 601(1), 151-158 (2014)
Palladium/silver-cocatalyzed tandem reactions of oxabenzonorbornadienes with substituted arylacetylenes: A simple method for the preparation of 1, 2-diarylethanones and 1, 2-diarylacetylenes.
Chen J, et al.
Organometallics, 34(17), 4318-4322 (2015)
Kideog Bae et al.
Analytical chemistry, 92(1), 740-748 (2019-11-22)
The dynamics of mitochondria in live cells play a pivotal role in biological events such as cell metabolism, early stage apoptosis, and cell differentiation. Triphenylphosphonium (TPP) is a commonly used mitochondria-targeting agent for mitochondrial studies. However, there has been a
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