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445134

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
Pricing and availability is not currently available.

Quality Level

100

Assay

98%

mp

86-89 °C (lit.)

functional group

hydroxyl
ketone
phenyl

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.[1]
  • Copper(II) complexes of 2-hydroxyacetophenone N-substituted thiosemicarbazones.[2]
  • Chromium, molybdenum, and ruthenium complexes of 2-hydroxyacetophenone Schiff bases.[3]
  • 2-Hydroxyacetophenone-aroyl hydrazone derivatives for inhibition of copper corrosion in nitric acid.[4]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL7349
MKCG1326
MKCD7205
MKCB1231V
MKBV8285V

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Synthetic studies on optically active Schiff-base ligands derived from condensation of 2-hydroxyacetophenone and chiral diamines.
Gao WT and Zheng Z.
Molecules (Basel), 7(7), 511-516 (2002)
A stereochemically well-defined rhodium (III) catalyst for asymmetric transfer hydrogenation of ketones
Matharu DS, et al.
Organic Letters, 7(24), 5489-5491 (2005)
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
2-Hydroxyacetophenone-aroyl hydrazone derivatives as corrosion inhibitors for copper dissolution in nitric acid solution
AS Fouda, et al.
Bulletin of the Korean Chemical Society,, 21(11), 1085-1089 (2000)
Solvent-free microwave-assisted Beckmann rearrangement of benzaldehyde and 2-hydroxyacetophenone oximes.
Loupy A and Regnier S.
Tetrahedron Letters, 40(34), 6221-6224 (1999)
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