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Merck
CN

165131

2,5-Hexanedione

≥98%

Synonym(s):

Acetonylacetone

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About This Item

Linear Formula:
CH3COCH2CH2COCH3
CAS Number:
110-13-4
Molecular Weight:
114.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24850126
EC Number:
203-738-3
Beilstein/REAXYS Number:
506525
MDL number:
MFCD00008792
Assay:
≥98%
Form:
liquid

Key Documents

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Product Name

2,5-Hexanedione, ≥98%

InChI key

OJVAMHKKJGICOG-UHFFFAOYSA-N

InChI

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

SMILES string

CC(=O)CCC(C)=O

vapor pressure

0.43 mmHg ( 20 °C)

assay

≥98%

form

liquid

refractive index

n20/D 1.425 (lit.)

bp

191 °C (lit.)

mp

−6-−5 °C (lit.)

solubility

alcohol: miscible
diethyl ether: miscible
water: miscible

density

0.973 g/mL at 25 °C (lit.)

functional group

ketone

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Application

2,5-Hexanedione was used as starting reagent in the synthesis of trans-2,5-dimethylpyrrolidine.
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.

General description

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Nervous system

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

174.2 °F - closed cup

flash_point_c

79 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7988V
WXBF4767V
WXBD8779V
WXBD2121V
WXBD5476V

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An improved synthesis of (-)-(2R, 5R)-2, 5-dimethylpyrrolidine.
Short RP, et al.
The Journal of Organic Chemistry, 54(7), 1755-1756 (1989)
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
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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