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105-45-3

Basic Information
CAS No.: 105-45-3
Name: Butanoic acid, 3-oxo-,methyl ester
Article Data: 104
Cas Database
Molecular Structure:
Molecular Structure of 105-45-3 (Butanoic acid, 3-oxo-,methyl ester)
Formula: C5H8O3
Molecular Weight: 116.117
Synonyms: Acetoaceticacid, methyl ester (6CI,8CI);3-Oxobutanoic acid methyl ester;3-Oxobutyricacid methyl ester;Acetoacetate methyl ester;Methyl 3-oxobutanoate;Methyl3-oxobutyrate;Methyl acetylacetate;
EINECS: 203-299-8
Density: 1.039 g/cm3
Melting Point: -80 °C
Boiling Point: 169.4 °C at 760 mmHg
Flash Point: 61.6 °C
Solubility: 460 g/L in water at 20 °C
Appearance: Colorless transparent liquid
Hazard Symbols: IrritantXi
Risk Codes: 36
Safety: 26
Transport Information: N/A
PSA: 43.37000
LogP: 0.13850
Synthetic route
67-56-1

methanol

72324-39-1

5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione

105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
for 0.0666667h; microwave irradiation;98%
for 5h; Reflux;

3-oxo-2-pyrrolidin-2-yl-butyric acid methyl ester hydrochloride

A

105-45-3

acetoacetic acid methyl ester

B

4-methyl-1,2,3,5a,6,7,8,8b-octahydro-3a,8a-diaza-as-indacene-5-carboxylic acid methyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuranA 49%
B 96%
67-56-1

methanol

201230-82-2

carbon monoxide

78-95-5

chloroacetone

105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With tributyl-amine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) at 110℃; under 11250.9 Torr; for 1h; Product distribution; Further Variations:; Reagents; Temperatures; time;95%
With tributyl-amine; bis-triphenylphosphine-palladium(II) chloride at 110℃; under 7500.6 Torr; for 2h;80%
67-56-1

methanol

5394-63-8

2,2,6-trimethyl-4H-1,3-dioxin-4-one

105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
Esterification;92%
In 5,5-dimethyl-1,3-cyclohexadiene Reflux;77%
at 110 - 120℃;72%
In 5,5-dimethyl-1,3-cyclohexadiene at 150℃;
67-56-1

methanol

1694-31-1

tert-butyl acetoacetate

105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With di(n-butyl)tin oxide In methanol for 12h; Heating;90%
In xylene Heating;
109514-04-7

-essigsaeure-methylester

A

79-20-9

acetic acid methyl ester

B

13253-76-4

acetic acid-(1-methoxy-vinyl ester)

C

2279-76-7

tripropyltin chloride

D

105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With acetyl chlorideA 18%
B 46%
C 88%
D 9%
67-56-1

methanol

77-92-9

citric acid

A

1830-54-2

3-oxopentanedioic acid dimethyl ester

B

100009-70-9

dimethyl 2-methoxypropene-1,3-dicarboxylate

C

20820-77-3

trimethyl aconitate

D

1587-20-8

trimethyl citrate

E

105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
Stage #1: citric acid With chlorosulfonic acid In dichloromethane at 10 - 15℃; for 5 - 6h;
Stage #2: methanol In dichloromethane at 3 - 35℃; for 2h; Conversion of starting material;
A 87.3%
B n/a
C n/a
D n/a
E n/a
70-11-1

α-bromoacetophenone

2911-22-0

6-methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine

A

105-45-3

acetoacetic acid methyl ester

B

5399-30-4

2-oxo-2-phenylethylthiocyanate

Conditions
ConditionsYield
With sodium methylate In methanol for 12h; Ambient temperature;A 29%
B 87%
623-43-8

crotonic acid methyl ester

105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With oxygen; nickel dichloride In methanol; water at 100℃; under 7500.75 Torr; for 12h; Reagent/catalyst; Solvent; Temperature; Autoclave;85.3%
79-20-9

acetic acid methyl ester

75-36-5

acetyl chloride

105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -45℃; 1.) 30 min, 2.) 90 min;84%
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    Name:Methyl acetoacetate The alias:Methyl acetoacetaten; Acetoacetic acid methyl ester; Butanoic acid, 3-oxo-, methyl ester:; methyl 3-oxobutanoate; MAA CAS NO:105-45-3 Molecular formula:C5H8O3 Molecular weight:116.1152 Product Quality 12 y

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Butanoic acid, 3-oxo-,methyl ester, with CAS registry number of 105-45-3, is also known as 3-Oxobutanoic acid methyl ester. Its EINECS registry number is 203-299-8. In addition, the formula is C5H8O3 and the molecular weight is 116.12. What's more, its systematic name is Methyl 3-oxobutanoate. Its classification code is Skin / Eye Irritant. This chemical is a colorless transparent liquid and should be stored in a cool, ventilated place away from fire and heat. It is used as a mixed solvent of cellulose acetate. It is also used as an intermediate for pesticides, pharmaceuticals and organic synthesis.

Physical properties about Butanoic acid, 3-oxo-,methyl ester are: (1)ACD/LogP: 0.19; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.18; (4)ACD/LogD (pH 7.4): 0.18; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 30.03; (8)ACD/KOC (pH 7.4): 30.01; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 43.37 Å2; (13)Index of Refraction: 1.399; (14)Molar Refractivity: 27.01 cm3; (15)Molar Volume: 111.6 cm3; (16)Polarizability: 10.71×10-24cm3; (17)Surface Tension: 29.7 dyne/cm; (18)Density: 1.039 g/cm3; (19)Flash Point: 61.6 °C; (20)Enthalpy of Vaporization: 40.58 kJ/mol; (21)Boiling Point: 169.4 °C at 760 mmHg; (22)Vapour Pressure: 1.54 mmHg at 25°C.

Preparation of Methyl acetylacetate: it is prepared by reaction of diketene with methanol. The reaction mixture is esterificated with catalyst of concentrated sulfuric acid. Then product is obtained by crude distillation and distillation. Besides, diketene is derived from cleavage of acetic acid.

C4H4O2 + CH3OH → C5H8O3

Uses of Butanoic acid, 3-oxo-,methyl ester: it can be used to produce 2-acetyl-5-(3-methoxy-phenyl)-pentanoic acid methyl ester by heating. It will need reagent K2CO3 and solvent acetone. The yield is about 67%.

Butanoic acid, 3-oxo-,methyl ester can be used to produce 2-acetyl-5-(3-methoxy-phenyl)-pentanoic acid methyl ester by heating

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(=O)CC(=O)OC
(2)InChI: InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3
(3)InChIKey: WRQNANDWMGAFTP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 3228mg/kg (3228mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 30, Pg. 63, 1948.