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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

Quality Level

100

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
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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ1146
MKCD1214
MKBW9003V
MKBT2243V
MKBR4868V

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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)
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)
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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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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