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Sigma-Aldrich

2,5-Hexandion

≥98%

Synonym(e):

Acetonylaceton

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About This Item

Lineare Formel:
CH3COCH2CH2COCH3
CAS-Nummer:
110-13-4
Molekulargewicht:
114.14
Beilstein:
506525
EG-Nummer:
203-738-3
MDL-Nummer:
MFCD00008792
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24850126
NACRES:
NA.22

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Dampfdruck

0.43 mmHg ( 20 °C)

Assay

≥98%

Form

liquid

Brechungsindex

n20/D 1.425 (lit.)

bp

191 °C (lit.)

mp (Schmelzpunkt)

−6-−5 °C (lit.)

Löslichkeit

alcohol: miscible
diethyl ether: miscible
water: miscible

Dichte

0.973 g/mL at 25 °C (lit.)

Funktionelle Gruppe

ketone

SMILES String

CC(=O)CCC(C)=O

InChI

1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3

InChIKey

OJVAMHKKJGICOG-UHFFFAOYSA-N

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Allgemeine Beschreibung

2,5-Hexanedione is a major metabolite of the neurotoxic industrial solvent methyl n-butyl ketone[1]. It reacts with amines to yield 2,5-dimethylpyrroles[2].

Anwendung

2,5-Hexanedione was used as starting reagent in the synthesis of trans-2,5-dimethylpyrrolidine[3].
It was used as reference standard for the determination of 2,5HD in human urine using gas chromatography-electron capture detection and gas chromatography-mass selective detection.[4]

Piktogramme

Health hazardExclamation mark
GHS08,GHS07

Signalwort

Warning

Gefahreneinstufungen

Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2

Zielorgane

Nervous system

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 2

Flammpunkt (°F)

174.2 °F - closed cup

Flammpunkt (°C)

79 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
WXBF4767V
WXBD8779V
WXBD2121V
WXBD5476V
WXBD2830V

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Die Dokumentenbibliothek aufrufen

D C Anthony et al.
Toxicology and applied pharmacology, 71(3), 372-382 (1983-12-01)
3,4-Dimethyl-2,5-hexanedione and 2,5-hexanedione were reacted with model amines to yield N-substituted 2,3,4,5-tetramethylpyrroles and 2,5-dimethylpyrroles, respectively. When compared to the unsubstituted parent compound 2,5-hexanedione, 3,4-dimethyl-2,5-hexanedione was found to cyclize approximately eight times as rapidly on a molar basis at 37 degrees
An improved synthesis of (-)-(2R, 5R)-2, 5-dimethylpyrrolidine.
Short RP, et al.
The Journal of Organic Chemistry, 54(7), 1755-1756 (1989)
E K Allard et al.
Toxicology and applied pharmacology, 137(2), 149-156 (1996-04-01)
The Sertoli cell toxicant 2,5-hexanedione (2,5-HD) causes irreversible testicular atrophy in rats. After toxicant exposure, only Sertoli cells, stem cells, and a few spermatogonia remain in the seminiferous epithelium. In this study, the number, type, and fate of the remaining
Gas chromatographic method for the sensitive determination of 2, 5-hexanedione using electron capture and mass-selective detection.
Konidari, C. N., C. D. Stalikas, and M. I. Karayannis
Analytica Chimica Acta, 442.2, 231-239 (2001)
Sarah N Campion et al.
Toxicological sciences : an official journal of the Society of Toxicology, 117(2), 466-474 (2010-07-10)
Germ cell apoptosis directly induced by x-radiation (x-ray) exposure is stage specific, with a higher incidence in stage II/III seminiferous tubules. A priming exposure to the Sertoli cell toxicant 2,5-hexanedione (HD) results in a marked reduction in x-ray-induced germ cell
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  1. 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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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    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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