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Sigma-Aldrich

2-Hydroxyacetophenone

98%

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About This Item

Linear Formula:
C6H5COCH2OH
CAS Number:
582-24-1
Molecular Weight:
136.15
EC Number:
209-480-8
MDL number:
MFCD00041829
UNSPSC Code:
12352100
PubChem Substance ID:
24868161
NACRES:
NA.22

Assay

98%

mp

86-89 °C (lit.)

SMILES string

OCC(=O)c1ccccc1

InChI

1S/C8H8O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,9H,6H2

InChI key

ZWVHTXAYIKBMEE-UHFFFAOYSA-N

Application

2-Hydroxyacetophenone can be used as a starting material for the synthesis of:
  • Enantioselective 1R-phenyl-1,2-ethanediol in the presence of a rhodium(III) catalyst by asymmetric transfer hydrogenation.
  • Copper(II) complexes of 2-hydroxyacetophenone N-substituted thiosemicarbazones.
  • Chromium, molybdenum, and ruthenium complexes of 2-hydroxyacetophenone Schiff bases.
  • 2-Hydroxyacetophenone-aroyl hydrazone derivatives for inhibition of copper corrosion in nitric acid.

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

11 - Combustible Solids

WGK

WGK 3

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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Ying-Heng Chen et al.
Journal of agricultural and food chemistry, 65(19), 3965-3974 (2017-04-30)
4-[2-(t-Butylamino)-1-hydroxyethyl]phenol (buctopamine, 4), a new β
Chromium, molybdenum and ruthenium complexes of 2-hydroxyacetophenone Schiff bases
Ali SA, et al.
Journal of Coordination Chemistry, 55(10), 1161-1170 (2002)
Resonance Raman intensity analysis of the excited-state proton transfer in 2-hydroxyacetophenone.
Peteanu LA and Mathies RA.
The Journal of Physical Chemistry, 96(17), 6910-6916 (1992)
Na Li et al.
Molecules (Basel, Switzerland), 25(14) (2020-07-28)
Fluorophores with aggregation-induced emission enhancement (AIEE) characteristics applied in bioimaging have attracted more and more attention in recent years. In this work, a series of flavanone compounds with AIEE characteristics was developed and applied to fluorescence imaging of mitochondria and
Mateusz Łużny et al.
Molecules (Basel, Switzerland), 24(17) (2019-09-05)
Biotransformations were performed on eight selected yeast strains, all of which were able to selectively hydrogenate the chalcone derivatives 3-(2"-furyl)- (1) and 3-(2"-thienyl)-1-(2'-hydroxyphenyl)-prop-2-en-1-one (3) into 3-(2"-furyl)- (2) and 3-(2"-thienyl)-1-(2'-hydroxyphenyl)-propan-1-one (4) respectively. The highest efficiency of hydrogenation of the double bond
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