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CAS No.: | 592-20-1 |
---|---|
Name: | ACETOXYACETONE |
Article Data: | 53 |
Molecular Structure: | |
Formula: | C5H8O3 |
Molecular Weight: | 116.117 |
Synonyms: | 2-Propanone,1-hydroxy-, acetate (8CI);2-Propanone, hydroxy-, acetate (6CI,7CI);1-(Acetyloxy)propan-2-one;1-Acetoxy-2-propanone;1-Acetoxyacetone;1-Hydroxy-2-propanone acetate;2-Oxopropyl acetate;Acetic acid acetonyl ester;Acetol acetate;Acetonyl acetate;Acetoxyacetone;Acetoxypropanone;Acetylmethyl acetate;Acetyloxyacetone;NSC 2298;NSC 7614;O-Acetylacetol; |
EINECS: | 209-746-3 |
Density: | 1.039 g/cm3 |
Melting Point: | 74.0-75.5 °C |
Boiling Point: | 153.7 °C at 760 mmHg |
Flash Point: | 51.9 °C |
Appearance: | clear pale yellow to amber liquid |
Safety: | 23-24/25 |
PSA: | 43.37000 |
LogP: | 0.13850 |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphineoxide)dioxouranium(VI) perchlorate In dichloromethane-d2 at 22℃; for 2.5h; | 99% |
Conditions | Yield |
---|---|
With 18-crown-6 ether In tetrahydrofuran for 2h; Heating; | 92% |
at 140 - 150℃; | |
In N,N-dimethyl-formamide at 100℃; for 21h; | |
In N,N-dimethyl-formamide at 100℃; for 21h; |
Conditions | Yield |
---|---|
In benzene for 2h; Inert atmosphere; Reflux; regioselective reaction; | 91% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; tetrabutylammomium bromide In acetone at 120℃; under 33753.4 Torr; for 0.5h; Inert atmosphere; Microwave irradiation; | 88% |
3,3-dimethyldioxirane
pentan-3-one
A
Acetol acetate
B
1-methyl-2-oxobutyl acetate
Conditions | Yield |
---|---|
In acetone Heating; Yields of byproduct given; | A n/a B 64.6% |
3,3-dimethyldioxirane
cyclohexanone
A
Acetol acetate
B
2-acetoxycyclohexanone
Conditions | Yield |
---|---|
In acetone Heating; | A n/a B 57.6% |
methanol
Acetyl(1-chlor-1-methylethyl)peroxid
A
Acetol acetate
B
Acetyl(1-methoxy-1-methylethyl)peroxid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In chloroform-d1 at 0℃; for 20h; Yields of byproduct given; | A n/a B 57% |
3,3-dimethyldioxirane
cyclopentanone
A
Acetol acetate
B
2-acetoxycyclopentanone
Conditions | Yield |
---|---|
In acetone Heating; | A n/a B 54.3% |
3,3-dimethyldioxirane
butanone
A
3-acetoxy-2-butanone
B
Acetol acetate
C
1-acetoxybutan-3-one
D
2-oxobutyl acetate
Conditions | Yield |
---|---|
In acetone Heating; Yields of byproduct given; | A 52.3% B n/a C n/a D n/a |
In acetone Heating; Yield given. Yields of byproduct given; |
ethylbenzene
3,3-dimethyldioxirane
A
Acetol acetate
B
1-Phenylethanol
C
1-phenylethyl acetate
D
acetophenone
Conditions | Yield |
---|---|
In acetone for 48h; Ambient temperature; Further byproducts given; | A n/a B 36% C 14 % Chromat. D 50% |
The IUPAC name of Acetoxyacetone is 2-oxopropyl acetate. With the CAS registry number 592-20-1, it is also named as 1-Hydroxy-2-propanone acetate. The product's categories are Acetyl Group; Ester Flavor. Besides, it is clear pale yellow to amber liquid, which should be stored in refrigerator. When you are using this chemical, please do not breathe vapour. And you should avoid contact with skin and eyes. In addition, its molecular formula is C5H8O3 and molecular weight is 116.11.
The other characteristics of this product can be summarized as: (1)EINECS: 209-746-3; (2)ACD/LogP: 0.33; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 0.33; (5)ACD/LogD (pH 7.4): 0.33; (6)ACD/BCF (pH 5.5): 1.05; (7)ACD/BCF (pH 7.4): 1.05; (8)ACD/KOC (pH 5.5): 36.15; (9)ACD/KOC (pH 7.4): 36.15; (10)#H bond acceptors: 3; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 3; (13)Polar Surface Area: 43.37 Å2; (14)Index of Refraction: 1.399; (15)Molar Refractivity: 27.01 cm3; (16)Molar Volume: 111.6 cm3; (17)Polarizability: 10.71×10-24cm3; (18)Surface Tension: 29.7 dyne/cm; (19)Density: 1.039 g/cm3; (20)Flash Point: 51.9 °C; (21)Enthalpy of Vaporization: 39.05 kJ/mol; (22)Boiling Point: 153.7 °C at 760 mmHg; (23)Vapour Pressure: 3.29 mmHg at 25 °C.
Preparation of Acetoxyacetone: this chemical can be prepared by the reaction of cyclohexanone with dimethyldioxirane.
This reaction needs acetone by heating. The yield is 57.6 %.
Uses of Acetoxyacetone: it can react with valeric acid phenyl ester to get 2-(2-acetoxy-1-hydroxy-1-methyl-ethyl)-pentanoic acid phenyl ester.
This reaction needs TiCl4, Et3N and CH2Cl2 at temperature of -78 °C. The yield is 60 %.
People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: CC(=O)COC(=O)C
(2)InChI: InChI=1S/C5H8O3/c1-4(6)3-8-5(2)7/h3H2,1-2H3
(3)InChIKey: DBERHVIZRVGDFO-UHFFFAOYSA-N