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Basic Information
CAS No.: 110-13-4
Name: Acetonylacetone
Article Data: 250
Molecular Structure:
Molecular Structure of 110-13-4 (Acetonylacetone)
Formula: C6H10O2
Molecular Weight: 114.144
Synonyms: 1,2-Diacetylethane;2,5-Diketohexane;2,5-Dioxohexane;Diacetonyl;NSC 7621;a,b-Diacetylethane;2,5-Hexanedione;
EINECS: 203-738-3
Density: 0.973 g/cm3
Melting Point: -6―-5 °C(lit.)
Boiling Point: 188.8 °C at 760 mmHg
Flash Point: 78.9 °C
Solubility: soluble in water
Appearance: clear slight brown liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/38-48/20/21/22-36/37/38
Safety: 23-26-36/37-37/39
PSA: 34.14000
LogP: 0.94460
Synthetic route
625-86-5

2,5-dimethylfuran

110-13-4

2,5-hexanedione

Conditions
ConditionsYield
With water at 100℃; for 2h;100%
With carbon dioxide In water at 150℃; under 30003 Torr; for 15h; Autoclave;95%
With carbon dioxide In water at 150℃; under 30003 Torr; for 15h; Autoclave;95%
1093613-53-6

(1R,4S,5S,6R)-1,4-dimethyl-2,3-dioxabicyclo[2.2.2]octane-5,6-diol

110-13-4

2,5-hexanedione

Conditions
ConditionsYield
In acetonitrile for 16h; Reflux;100%
2935-44-6

hexane-2,5-diol

110-13-4

2,5-hexanedione

Conditions
ConditionsYield
With dihydrogen peroxide; Na12[WZn3(H2O)2(ZnW9O34)2] at 75℃; for 7h;99%
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 4.25h; Oxidation;98%
With 2O34W9Zn(12-)*W(6+)*3Zn(2+)*2H2O; dihydrogen peroxide In water; acetonitrile at 135℃; under 2250.23 Torr; for 0.25h; Microwave irradiation;93%
With chromium(III) oxide; copper at 190℃;
With AmberliteIR-120(H) at 90℃; for 24h; Autoclave; Inert atmosphere;> 99 %Chromat.
4436-75-3

3-hexene-2,5-dione

110-13-4

2,5-hexanedione

Conditions
ConditionsYield
With nickel phosphide; hydrogen In water at 100℃; under 15201 Torr; for 1h;96%
944-26-3

hexane-2,5-dione bis-ethylene ketal

110-13-4

2,5-hexanedione

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane for 3h; Ambient temperature;95%
13891-87-7

pent-4-en-2-one

75-07-0

acetaldehyde

110-13-4

2,5-hexanedione

Conditions
ConditionsYield
With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; caesium carbonate In tetrahydrofuran at 20℃; for 24h; Stetter reaction; Inert atmosphere;95%
61759-13-5

1-(phenylselanyl)propan-2-one

A

1666-13-3

diphenyl diselenide

B

110-13-4

2,5-hexanedione

Conditions
ConditionsYield
at 600℃; under 20 Torr; for 0.0333333h;A 93%
B 52%
69924-30-7

5-hydroxymethyl-tetrahydrofuran-2-carbaldehyde

A

1003-38-9

2,5-dimethyltetrahydrofuran

C

625-86-5

2,5-dimethylfuran

D

110-13-4

2,5-hexanedione

E

37493-29-1

5-methyltetrahydro-2-furaldehyde

Conditions
ConditionsYield
With hydrogen In 1,4-dioxane at 180℃; under 9000.9 Torr; for 4h; Catalytic behavior; Overall yield = 100 %;A 1.4%
B 3.6%
C 91.5%
D 3.2%
E n/a
With hydrogen In 1,4-dioxane at 180℃; under 9000.9 Torr; for 4h; Catalytic behavior; Overall yield = 100 %;A 9.5%
B 4.9%
C 80.1%
D 3.4%
E n/a
318511-70-5

tert-butyl 2-acetyl-4-oxopentanoate

110-13-4

2,5-hexanedione

Conditions
ConditionsYield
With sulfuric acid at 60 - 70℃; for 8h;90.9%
With toluene-4-sulfonic acid
35223-72-4

5-nitro-2-hexanone

110-13-4

2,5-hexanedione

Conditions
ConditionsYield
With tetrabutylammomium bromide; oxygen In acetonitrile for 2h; electrolysis;86%
With sodium hydroxide; sodium chlorite; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 7h; Ambient temperature;78%
With sodium nitrite In water; dimethyl sulfoxide at 65℃;75%
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  • Acetonyl acetone 2,5-hexanedione

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    Acetonyl acetone 2,5-hexanedione

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The 2,5-Hexanedione, with the CAS registry number 110-13-4, is also known as 1,2-Diacetylethane. It belongs to the product categories of Pharmaceutical Intermediates; Ketone. Its EINECS registry number is 203-738-3. This chemical's molecular formula is C6H10O2 and molecular weight is 114.1424. Its IUPAC name is called hexane-2,5-dione. This chemical's classification codes are Cholinergic Agents; Cholinesterase Inhibitors; Cross-Linking Reagents; Enzyme Inhibitors; Indicators and Reagents; Mutation data; Neurotoxins; Neurotransmitter Agents; Noxae; Reproductive Effect; Skin / Eye Irritant. This chemical is colourless to pale yellow liquid. It can be used to synthetize resin, nitro paint, stains and printing inks.

Physical properties of 2,5-Hexanedione: (1)ACD/LogP: -0.27; (2)ACD/LogD (pH 5.5): -0.27; (3)ACD/LogD (pH 7.4): -0.27; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 16.98; (7)ACD/KOC (pH 7.4): 16.98; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.405; (11)Molar Refractivity: 29.9 cm3; (12)Molar Volume: 121.8 cm3; (13)Surface Tension: 28.3 dyne/cm; (14)Density: 0.936 g/cm3; (15)Flash Point: 78.9 °C; (16)Enthalpy of Vaporization: 42.5 kJ/mol; (17)Boiling Point: 188.8 °C at 760 mmHg; (18)Vapour Pressure: 0.587 mmHg at 25°C.

Preparation: this chemical can be prepared by 2,5-dimethyl-furan. This reaction will need reagent glacial acetic acid, sulfuric acid and water.

Uses of 2,5-Hexanedione: it can be used to produce 2-(2,5-dimethyl-pyrrol-1-yl)-thiazole at temperature of 100 °C. This reaction will need reagent POCl3 and solvent toluene with reaction time of 4 hours. The yield is about 5%.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes and may cause damage to health. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(=O)CCC(=O)C
(2)InChI: InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3
(3)InChIKey: OJVAMHKKJGICOG-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 skin 6600uL/kg (6.6mL/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944.
mouse LD50 intraperitoneal 1600mg/kg (1600mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4777, 1982.
mouse LD50 oral 2386mg/kg (2386mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 45, Pg. 669, 1956.
rat LCLo inhalation 2000ppm/4H (2000ppm)   Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 343, 1949.
rat LD50 intraperitoneal 800mg/kg (800mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4777, 1982.
rat LD50 oral 2076mg/kg (2076mg/kg)   Indian Journal of Experimental Biology. Vol. 24, Pg. 371, 1986.