Synthesis Mechanism of Toxicity
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2,5-Hexanedione

Synthesis Mechanism of Toxicity
Product Name
2,5-Hexanedione
CAS No.
110-13-4
Chemical Name
2,5-Hexanedione
Synonyms
2,5-HEXANEDIONE;Hexane-2,5-dione;Hexanedione;acan;2,5-Hexadione;2,5-dione;2,5-HEXANDIONE;NSC 7621;Diacetonyl;hexane-2,5-
CBNumber
CB2455570
Molecular Formula
C6H10O2
Formula Weight
114.14
MOL File
110-13-4.mol
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2,5-Hexanedione Property

Melting point:
-6--5 °C (lit.)
Boiling point:
191 °C (lit.)
Density 
0.973 g/mL at 25 °C (lit.)
vapor pressure 
0.43 mm Hg ( 20 °C)
refractive index 
n20/D 1.425(lit.)
Flash point:
174 °F
storage temp. 
Store below +30°C.
solubility 
alcohol: miscible; Miscible with water, ethylalcohol and ether,ess. oils and perfume materials.
form 
Liquid
color 
Clear yellow to brown
Odor
Pleasant, sweet-ethereal odor.
PH
6.1 (10g/l, H2O, 20℃)
explosive limit
1.5%(V)
Water Solubility 
miscible
Merck 
14,71
BRN 
506525
Stability:
Stable. Incompatible with strong bases, strong reducing agents, strong oxidizing agents. Flammable.
InChIKey
OJVAMHKKJGICOG-UHFFFAOYSA-N
LogP
-0.270
CAS DataBase Reference
110-13-4(CAS DataBase Reference)
NIST Chemistry Reference
CH3COCH2CH2COCH3(110-13-4)
EPA Substance Registry System
2,5-Hexanedione (110-13-4)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
36/38-48/20/21/22-36/37/38
Safety Statements 
23-26-36/37-37/39
WGK Germany 
2
RTECS 
MO3150000
F 
8
Autoignition Temperature
400 °C
TSCA 
Yes
HS Code 
29141990
Toxicity
LD50 orally in rats: 2.7 g/kg (Smyth, Carpenter)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.00105
Product name
2,5-Hexanedione
Purity
for synthesis
Packaging
100mL
Price
$116
Updated
2024/03/01
Sigma-Aldrich
Product number
8.00105
Product name
2,5-Hexanedione
Purity
for synthesis
Packaging
250ML
Price
$168
Updated
2024/03/01
Sigma-Aldrich
Product number
15972
Product name
2,5-Hexanedione
Purity
analytical standard
Packaging
5ml
Price
$121
Updated
2022/05/15
TCI Chemical
Product number
H0101
Product name
Acetonylacetone
Purity
>97.0%(GC)
Packaging
25mL
Price
$38
Updated
2024/03/01
TCI Chemical
Product number
H0101
Product name
Acetonylacetone
Purity
>97.0%(GC)
Packaging
100mL
Price
$90
Updated
2024/03/01
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2,5-Hexanedione Chemical Properties,Usage,Production

Synthesis

2,5-Hexanedione has been prepared in several ways. A common method involves hydrolysis of 2,5-dimethylfuran, a glucose derived heterocycle.

Mechanism of Toxicity

Identification of 2,5-hexanedione as the major neurotoxic metabolite of n-hexane proceeded rapidly after its discovery as a urinary metabolite. 2,5-Hexanedione has been found to produce a polyneuropathy indistinguishable from n-hexane. 2,5-Hexanedione is many times more potent than n-hexane, the parent compound, in causing neurotoxicity in experimental animals. It appears that the neurotoxicity of 2,5-hexanedione resides in its γ-diketone structure since 2,3-, 2,4-hexanedione and 2,6-heptanedione are not neurotoxic, while 2,5-heptanedione and 3,6-octanedione and other γ-diketones are neurotoxic.

Description

2, 5-hexadione (2,5HD) is a flammable, transparent colorless to amber water-soluble liquid that is a multifunctional platform chemical, a major metabolite of n-hexane, and a key intermediate for the production of high energy density aviation fuels from biomass resources. It has a sweet aromatic smell and neurotoxic effects. It can be used as a high energy density fuel additive of platform chemicals, and can induce ovarian granulosa cell cycle arrest to establish ovarian injury model. It can also be used for biological monitoring of 2, 5-hexanedione exposure to n-hexane[1-2].

Chemical Properties

colourless to pale yellow liquid

Uses

2,5-Hexanedione is used as a reagent in the preparation of trans-2,5-dimethylpyrrolidine. It is also used in the synthesis of 2,5-dimethylpyrroles. Further, it plays an important role as a reagent used for the protection of amino groups in amino sugars and nucleosides. In addition to this, it is used in the preparation of five-membered heterocycles like indane-type and benzannulated systems. It is also employed as a precursor in Diels-alder cycloaddition reactions.

Uses

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.

Uses

It is the metabolite implicated in n-hexane neurotoxicity.

Application

2,5-Hexanedione is a neurotoxic metabolite of n-hexanes and methyl n-butyl ketone. It is also used as the starting material for diels-alder cycloaddition reactions, such as a reactions with amines to form 2,5-dimethylpyrroles.

Preparation


20 g of diethyl 2,3-diacetylbutanedioate are mechanically shaken for several days with 250 ml (excess) of 5% aqueous sodium hydroxide, and until no diethyl 2,3-diacetylbutanedioate separates on acidification of a sample with dilute hydrochloric acid. The solution is then saturated with potassium carbonate and extracted with ether, the extract is washed with brine to remove alcohol, dried over calcium chloride, and distilled, the fraction 192-198° C being retained. You can get 2,5-Hexanedione with a yield of 70%. Colourless liquid; agreeable odour; miscible with water, alcohol and ether; m.p. 9° C; b.p. 194° C; d=0.973 g/ml at 20° C.

Definition

ChEBI: A diketone that is hexane substituted by oxo groups at positions 2 and 5. It is a toxic metabolite of hexane and of 2-hexanone

Synthesis Reference(s)

Canadian Journal of Chemistry, 59, p. 945, 1981 DOI: 10.1139/v81-137
Journal of the American Chemical Society, 105, p. 7200, 1983 DOI: 10.1021/ja00362a047
Tetrahedron Letters, 15, p. 4149, 1974

General Description

Clear colorless to amber liquid with a sweet aromatic odor.

Air & Water Reactions

Highly flammable. Water soluble.

Reactivity Profile

Acetonylacetone is incompatible with oxidizing agents. Acetonylacetone is also incompatible with strong bases and strong reducing agents.

Fire Hazard

Acetonylacetone is combustible.

Purification Methods

Purify it by dissolving in Et2O, stiring with K2CO3 (a quarter of the weight of dione), filtering, drying over anhydrous Na2SO4 (not CaCl2), filtering again, evaporating the filtrate and distilling it in a vacuum. It is then redistilled through a 30cm Vigreux column (p 11, oil bath temperature 150o). It is miscible with H2O and EtOH. The dioxime has m 137o (plates from *C6H6), the mono-oxime has b 130o/11mm, and the 2,4-dinitrophenylhydrazone has m 210-212o (red needles from EtOH). It forms complexes with many metals. [Werner et al. Chem Ber 22 2100 1989, for enol content see Gero J Org Chem 19 1960 1954, Beilstein 1 IV 3688.]

References

[1] KAIXUAN ZHOU, Xin L, Chenggong Sun. Directed glycerol conversion to 2,5-hexanedione and more advanced poly-oxygenates as platform chemicals and high energy–density fuel additives[J]. Chemical Engineering Journal, 2022, 430: Article 132981. DOI:10.1016/j.cej.2021.132981.
[2] XUEMING XU. The Wnt/β-catenin pathway is involved in 2,5-hexanedione-induced ovarian granulosa cell cycle arrest[J]. Ecotoxicology and Environmental Safety, 2023, 268: Article 115720. DOI:10.1016/j.ecoenv.2023.115720.

2,5-Hexanedione Preparation Products And Raw materials

Raw materials

2,5-Dimethylfuran IODINE PURE 2,3-Butanedione Potassium carbonate ETHYL ACETOACETATE SODIUM SALT

Preparation Products

2,5-Dimethyl-1H-pyrrole 5-Methylisoxazole-3-carboxylic acid 1-[2,6-DICHLORO-4-(TRIFLUOROMETHYL)PHENYL]-2,5-DIMETHYL-1H-PYRROLE-3-CARBALDEHYDE 2,5-Dimethylthiophene Ascorbic Acid Methyl 3-methyl-2-butenoate
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View Lastest Price from 2,5-Hexanedione manufacturers

Jinan Finer Chemical Co., Ltd
Product
Acetonylacetone 110-13-4
Price
US $5.00/kg
Min. Order
1kg
Purity
≥99%
Supply Ability
100mt/year
Release date
2024-05-29
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Acetonylacetone 110-13-4
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-24
Hebei Weibang Biotechnology Co., Ltd
Product
Acetonylacetone 110-13-4
Price
US $100.00/KG
Min. Order
1KG
Purity
99%min
Supply Ability
200TON
Release date
2024-10-30

110-13-4, 2,5-HexanedioneRelated Search:

1,1,1-TRIFLUORO-5,5-DIMETHYL-2,4-HEXANEDIONE 2-ACETYL-1,3-CYCLOHEXANEDIONE Dimedone 4,4,5,5,6,6,6-HEPTAFLUORO-1-PHENYL-1,3-HEXANEDIONE 1,4-Cyclohexanedione mono(2,2-dimethyltrimethylene ketal) 5-PHENYLCYCLOHEXANE-1,3-DIONE RHODIZONIC ACID DIPOTASSIUM SALT 3,4-DIACETYL-2,5-HEXANEDIONE RHODIZONIC ACID DIHYDRATE QUASSIN Sodium rhodizonate Adrenosterone Diethyl succinosuccinate 2,3-DIHYDRO-9,10-DIHYDROXY-1,4-ANTHRACENEDIONE 1,4-Cyclohexanedione HYDRINDANTIN 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester 1,3-Cyclohexanedione

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