328103
3′-Hydroxyacetophenone
≥99%
Synonym(s):
1-(3-Hydroxyphenyl)ethanone, 3-Acetylphenol, 3-Hydroxyphenylethanone, m-Hydroxyacetophenone
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About This Item
Linear Formula:
HOC6H4COCH3
CAS Number:
Molecular Weight:
136.15
Beilstein:
2040676
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
≥99%
bp
296 °C (lit.)
mp
90-95 °C (lit.)
density
1.1 g/mL at 25 °C (lit.)
functional group
ketone
SMILES string
CC(=O)c1cccc(O)c1
InChI
1S/C8H8O2/c1-6(9)7-3-2-4-8(10)5-7/h2-5,10H,1H3
InChI key
LUJMEECXHPYQOF-UHFFFAOYSA-N
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General description
3′-Hydroxyacetophenone is an hydroxy-substituted alkyl phenyl ketone.
Application
3′-Hydroxyacetophenone was used in synthesis of enantiopure (-)-rivastigmine. It was also used in preparation of building block for synthesis of dendritic compounds.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
247.3 °F - closed cup
Flash Point(C)
119.6 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Katharine Moore Tibbetts et al.
The journal of physical chemistry. A, 118(37), 8170-8176 (2014-03-01)
The hydroxy-substituted alkyl phenyl ketones 2'-, 3'- and 4'- (ortho, meta, and para) hydroxyacetophenone were excited in the strong-field regime with wavelengths ranging from 1200-1500 nm to produce the respective radical cations. For 2'- and 3'-hydroxyacetophenone, the parent molecular ion
Synthesis of polyester dendrimers and dendrons starting from Michael reaction of acrylates with 3-hydroxyacetophenone.
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Tetrahedron Letters, 46(6), 1027-1030 (2005)
Kiwon Han et al.
The Journal of organic chemistry, 75(9), 3105-3108 (2010-03-30)
A practical and efficient procedure for the synthesis of rivastigmine was developed. This procedure includes dynamic kinetic resolution using a polymer-bound ruthenium complex and a lipase in combination as a key step. Enantiopure (-)-rivastigmine was obtained from commercially available 3'-hydroxyacetophenone
Takashi Otani et al.
Bioorganic & medicinal chemistry letters, 18(12), 3582-3584 (2008-05-31)
m-Acetylphenyl-beta-d-glucopyranosides and m-acetylphenyl-alpha/beta-d-mannopyranosides were synthesized by the Koenigs-Knorr, Mitsunobu, and Helferich reactions as key glycosylation reactions, respectively. Their spectroscopic properties and antioxidative activities were characterized as potential ultraviolet B-ray absorbents.
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