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278564

Sigma-Aldrich

4′-Hydroxyacetophenone

99%

Synonym(s):

4-Hydroxyphenylethanone, p-Acetophenol, p-Hydroxyphenyl methyl ketone, Piceol

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About This Item

Linear Formula:
HOC6H4COCH3
CAS Number:
99-93-4
Molecular Weight:
136.15
Beilstein:
774355
EC Number:
202-802-8
MDL number:
MFCD00002359
UNSPSC Code:
12352100
PubChem Substance ID:
24856821
NACRES:
NA.22
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Quality Level

200

Assay

99%

form

solid

bp

147-148 °C/3 mmHg (lit.)

mp

109-111 °C (lit.)

solubility

95% ethanol: 5%, colorless to faintly yellow

functional group

ketone

SMILES string

CC(=O)c1ccc(O)cc1

InChI

1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3

InChI key

TXFPEBPIARQUIG-UHFFFAOYSA-N

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General description

Molecular dynamics simulation study of the two known polymorphs of 4′-hydroxyacetophenone (form I, monoclinic; form II, orthorhombic) has been described[1].

Application

4′-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions[2].

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319,H412

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 1

Flash Point(F)

330.8 °F

Flash Point(C)

166 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3853
BCCC9897
BCBV5820
BCBN8497V
BCBL7971V

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Colbie R Chinowsky et al.
Molecular biology of the cell, 31(25), 2803-2815 (2020-10-08)
Brush border microvilli enable functions that are critical for epithelial homeostasis, including solute uptake and host defense. However, the mechanisms that regulate the assembly and morphology of these protrusions are poorly understood. The parallel actin bundles that support microvilli have
Ebru Mete et al.
Molecules (Basel, Switzerland), 12(12), 2579-2588 (2008-02-09)
1-Aryl-3-phenethylamino-1-propanone hydrochlorides 1-10, which are potentialpotent cytotoxic agents, were synthesized via Mannich reactions using paraformaldehyde,phenethylamine hydrochloride as the amine component and acetophenone, 4'-methyl-, 4'-methoxy-, 4'-chloro-, 4'-fluoro-, 4'-bromo-, 2',4'-dichloro-, 4'-nitro-, 4'-hydroxyacetophenone or 2-acetylthiophene as the ketone component. Yields were in the87-98
Carlos E S Bernardes et al.
The journal of physical chemistry. B, 116(17), 5179-5184 (2012-04-12)
A molecular dynamics simulation study of the two known polymorphs of 4′-hydroxyacetophenone (HAP; form I, monoclinic; form II, orthorhombic) is described. The modeling of the lattice energetics was found to be particularly sensitive to the atomic point charge (APC) selection
Peng Zuo et al.
The Journal of organic chemistry, 70(22), 8661-8675 (2005-10-22)
[reaction; see text] Picosecond and nanosecond time-resolved resonance Raman (TR(3)) spectroscopy was employed to investigate the deprotonation/ionization reaction of p-hydroxyacetophenone (HA) after ultraviolet photolysis in water solution. The TR(3) spectra in conjunction with density functional theory (DFT) calculations were used
N Vrchotová et al.
Environmental pollution (Barking, Essex : 1987), 131(1), 55-59 (2004-06-24)
The amount of catechin and 4-hydroxyacetophenone in the methanolic extract of the Norway spruce needles at the locality Bílý Kríz (Moravian-Silesian Beskydy Mts.) was found in the range 2.8-12.1 mg g(-1) (dry weight) and 0.2-17.7 mg g(-1) (dry weight), respectively.
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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