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328103

Sigma-Aldrich

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:
121-71-1
Molecular Weight:
136.15
Beilstein/REAXYS Number:
2040676
EC Number:
204-494-0
MDL number:
MFCD00002298
UNSPSC Code:
12352100
PubChem Substance ID:
24859714
NACRES:
NA.22

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

247.3 °F - closed cup

flash_point_c

119.6 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBC8212V
SHBK2858
SHBH0449V
SHBB9189V
57196PKV

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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.
Hirayama Y, et a
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.
Stefania Ferrari et al.
Journal of medicinal chemistry, 54(1), 211-221 (2010-12-04)
Folate analogue inhibitors of Leishmania major pteridine reductase (PTR1) are potential antiparasitic drug candidates for combined therapy with dihydrofolate reductase (DHFR) inhibitors. To identify new molecules with specificity for PTR1, we carried out a virtual screening of the Available Chemicals
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