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105-45-3

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105-45-3 Usage

Chemical Description

Methyl acetoacetate is a colorless liquid with a fruity odor, commonly used as a flavoring agent and in the production of pharmaceuticals.

Chemical Properties

Colorless, clear liquid

Uses

Different sources of media describe the Uses of 105-45-3 differently. You can refer to the following data:
1. Methyl acetoacetate (MAA) is a starting material for the syntheses of alpha-substituted aceto- acetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives.
2. 3-Oxobutanoic Acid Methyl Ester is a chemical reagent used in the synthesis of pharmaceuticals. It participates in the Biginelli reaction, forming molecules including dihydropyrimidinones.
3. Methyl acetoacetate is used as a chemical reagent used in the synthesis of pharmaceuticals. It participates in the Biginelli reaction, forming molecules including dihydropyrimidinones.Methyl acetoacetate (MAA) is used for the synthesis of alpha-substituted aceto- acetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives.

Production Methods

Methyl acetoacetate is produced by a reaction of methyl acetate with sodium methoxide.

General Description

A clear colorless liquid. Flash point 158°F. Denser than water and slightly soluble in water. Vapors heavier than air.

Air & Water Reactions

Very slightly soluble in water.

Reactivity Profile

Methyl acetoacetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides

Hazard

Toxic by ingestion and inhalation.

Health Hazard

May be harmful by inhalation, ingestion, or skin absorption. Causes eye irritation. May cause skin irritation.

Safety Profile

Moderately toxic by ingestion. A skin and severe eye irritant. Combustible when exposed to heat or flame. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

Carcinogenicity

Not listed by ACGIH, IARC, NTP, or California Proposition 65.

Check Digit Verification of cas no

The CAS Registry Mumber 105-45-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 5 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 105-45:
(5*1)+(4*0)+(3*5)+(2*4)+(1*5)=33
33 % 10 = 3
So 105-45-3 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3

105-45-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • Alfa Aesar

  • (A13696)  Methyl acetoacetate, 99%   

  • 105-45-3

  • 250g

  • 153.0CNY

  • Detail
  • Alfa Aesar

  • (A13696)  Methyl acetoacetate, 99%   

  • 105-45-3

  • 1000g

  • 347.0CNY

  • Detail
  • Alfa Aesar

  • (A13696)  Methyl acetoacetate, 99%   

  • 105-45-3

  • 5000g

  • 1456.0CNY

  • Detail
  • Sigma-Aldrich

  • (14610)  Methylacetoacetate  analytical standard

  • 105-45-3

  • 14610-5ML-F

  • 620.10CNY

  • Detail

105-45-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl acetoacetate

1.2 Other means of identification

Product number -
Other names Methyl 3-oxobutanoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:105-45-3 SDS

105-45-3Synthetic route

methanol
67-56-1

methanol

5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione
72324-39-1

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

acetoacetic acid methyl ester
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

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

A

acetoacetic acid methyl ester
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

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%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

chloroacetone
78-95-5

chloroacetone

acetoacetic acid methyl ester
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%
methanol
67-56-1

methanol

2,2,6-trimethyl-4H-1,3-dioxin-4-one
5394-63-8

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

acetoacetic acid methyl ester
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℃;
methanol
67-56-1

methanol

tert-butyl acetoacetate
1694-31-1

tert-butyl acetoacetate

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

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

-essigsaeure-methylester

A

acetic acid methyl ester
79-20-9

acetic acid methyl ester

B

acetic acid-(1-methoxy-vinyl ester)
13253-76-4

acetic acid-(1-methoxy-vinyl ester)

C

tripropyltin chloride
2279-76-7

tripropyltin chloride

D

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

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

methanol

citric acid
77-92-9

citric acid

A

3-oxopentanedioic acid dimethyl ester
1830-54-2

3-oxopentanedioic acid dimethyl ester

B

dimethyl 2-methoxypropene-1,3-dicarboxylate
100009-70-9

dimethyl 2-methoxypropene-1,3-dicarboxylate

C

trimethyl aconitate
20820-77-3

trimethyl aconitate

D

trimethyl citrate
1587-20-8

trimethyl citrate

E

acetoacetic acid methyl ester
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
α-bromoacetophenone
70-11-1

α-bromoacetophenone

6-methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine
2911-22-0

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

A

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

B

2-oxo-2-phenylethylthiocyanate
5399-30-4

2-oxo-2-phenylethylthiocyanate

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

crotonic acid methyl ester

acetoacetic 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%
acetic acid methyl ester
79-20-9

acetic acid methyl ester

acetyl chloride
75-36-5

acetyl chloride

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -45℃; 1.) 30 min, 2.) 90 min;84%
acetic acid methyl ester
79-20-9

acetic acid methyl ester

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 20h; Heating;83%
With sodium methylate at 60℃;
With sodium anschliessend mit Essigsaeure oder Kohlendioxyd;
methanol
67-56-1

methanol

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

acetyl chloride
75-36-5

acetyl chloride

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
Stage #1: cycl-isopropylidene malonate; acetyl chloride With pyridine In dichloromethane at 20℃; for 2h;
Stage #2: methanol In dichloromethane for 2h; Further stages.;
75%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With methanol; water; oxygen; toluene-4-sulfonic acid; palladium dichloride In N,N-dimethyl acetamide at 80℃; under 4560.31 Torr; for 3h; Autoclave; regioselective reaction;73%
With tert.-butylhydroperoxide; sodium tetrachloropalladate(II) In acetic acid; tert-butyl alcohol at 50℃; for 3h;
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

methanol
67-56-1

methanol

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
for 4.5h; Heating;72.5%
With dmap
1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 0.343333h;
methanol
67-56-1

methanol

2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine
2911-21-9

2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine

A

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

B

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With triethylamine for 24h; Heating;A 70%
B 15%
tert-butyl acetoacetate
1694-31-1

tert-butyl acetoacetate

A

tert-butyl nitrate
926-05-6

tert-butyl nitrate

B

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With nitric acid In dichloromethane at 0℃; for 2h;A 60%
B 20%
6-methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine
2911-22-0

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

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With sodium methylate In methanol Ambient temperature;57%
1,2-Dimethyl-2-<(methoxycarbonyl)methyl>-1,3-dithiolanium-tetrafluoroborat

1,2-Dimethyl-2-<(methoxycarbonyl)methyl>-1,3-dithiolanium-tetrafluoroborat

A

2-methylsulfanyl-ethanethiol
22322-43-6

2-methylsulfanyl-ethanethiol

B

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With water at 40℃; for 0.0833333h;A 56%
B 13%
methyl but-3-enoate
3724-55-8

methyl but-3-enoate

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With manganese(IV) oxide; palladium dichloride In water; acetonitrile at 60℃; for 26h;52%
1-(3,5-dimethyl-1H-pyrazol-1-yl)ethanone
10199-63-0

1-(3,5-dimethyl-1H-pyrazol-1-yl)ethanone

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With zinc In tetrahydrofuran for 1h; Heating;50%
β-(N,N-dimethoxyamino)-isovaleric acid methyl ester
70569-71-0

β-(N,N-dimethoxyamino)-isovaleric acid methyl ester

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrachloromethane at 20℃;43.8%
1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene
74590-73-1

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene

acetyl chloride
75-36-5

acetyl chloride

A

3,5-dioxohexanoic acid methyl ester
29736-80-9

3,5-dioxohexanoic acid methyl ester

B

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
In diethyl ether at -78℃; for 4h; Yields of byproduct given;A 30%
B n/a
acetic acid methyl ester
79-20-9

acetic acid methyl ester

methyl (2SR,3RS)-1-benzyl-2-(indol-3-yl)piperidine-3-carboxylate

methyl (2SR,3RS)-1-benzyl-2-(indol-3-yl)piperidine-3-carboxylate

A

methyl 5-hydroxy-2-methoxycarbonyl-5-methyl-3-oxocyclohexen-1-acetate
1427722-55-1

methyl 5-hydroxy-2-methoxycarbonyl-5-methyl-3-oxocyclohexen-1-acetate

B

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
Stage #1: acetic acid methyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: methyl (2SR,3RS)-1-benzyl-2-(indol-3-yl)piperidine-3-carboxylate In tetrahydrofuran at 0℃; for 15h;
A 27%
B 24%
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
771-03-9

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

3,5-dioxohexanoic acid methyl ester
29736-80-9

3,5-dioxohexanoic acid methyl ester

C

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With sodium methylate In methanol; benzene for 18h; Heating;A 7%
B 18%
C 16%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

Dimethyl phosphite
868-85-9

Dimethyl phosphite

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
sulfuric acid at 50℃; for 90h;13%
methanol
67-56-1

methanol

ethyl (E)-2-acetyl-3-oxo-5-phenylpent-4-enoate
76352-65-3

ethyl (E)-2-acetyl-3-oxo-5-phenylpent-4-enoate

sodium methylate
124-41-4

sodium methylate

A

acetic acid methyl ester
79-20-9

acetic acid methyl ester

B

methyl 3-oxo-5-phenyl-4-pentenoate
42996-88-3

methyl 3-oxo-5-phenyl-4-pentenoate

C

Methyl cinnamate
103-26-4

Methyl cinnamate

D

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

3-hydroxybutyric acid methyl ester
1487-49-6

3-hydroxybutyric acid methyl ester

A

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

B

acetone
67-64-1

acetone

Conditions
ConditionsYield
With copper at 330℃;
acetic acid methyl ester
79-20-9

acetic acid methyl ester

sodium methylate
124-41-4

sodium methylate

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
at 57 - 80℃; Selbstkondensation;
cyclobutane-1,3-dione
15506-53-3

cyclobutane-1,3-dione

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With methanol; sodium methylate
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 2-chloroacetoacetate
4755-81-1

methyl 2-chloroacetoacetate

Conditions
ConditionsYield
With sulfuryl dichloride; 2,2'-azobis(isobutyronitrile) In benzene at 20℃; for 2h; Inert atmosphere;100%
With sulfuryl dichloride In dichloromethane for 1h; Ambient temperature;98%
With ammonium cerium(IV) nitrate at 25 - 28℃; for 3h;85%
With sulfuryl dichloride
With sulfuryl dichloride at 0℃;
benzaldehyde
100-52-7

benzaldehyde

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

5-hydroxy-3-oxo-5-phenyl-valeric acid methyl ester
53063-63-1

5-hydroxy-3-oxo-5-phenyl-valeric acid methyl ester

Conditions
ConditionsYield
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.333333h;
Stage #3: benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 1.08333h;
100%
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -15 - -10℃; for 0.5h; Inert atmosphere;
Stage #3: benzaldehyde Further stages;
92%
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -15 - -10℃; for 0.5h;
Stage #3: benzaldehyde Further stages;
92%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

prenyl bromide
870-63-3

prenyl bromide

methyl 7-methyl-3-oxooct-6-enoate
53067-23-5

methyl 7-methyl-3-oxooct-6-enoate

Conditions
ConditionsYield
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; mineral oil for 0.166667h;
Stage #3: prenyl bromide In tetrahydrofuran; mineral oil for 0.0833333h;
100%
With n-butyllithium; sodium hydride In tetrahydrofuran at 0 - 20℃;100%
With n-butyllithium; sodium hydride In tetrahydrofuran at 0℃;79%
1-(2-aminoethyl)pyrrolidine
7154-73-6

1-(2-aminoethyl)pyrrolidine

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 3-<(2'-(pyrrolidin-1but-2-enoate" src="//file1.lookchem.com/cas/reactions/2021/07/13/6396035.png_ms" />

methyl 3-<(2'-(pyrrolidin-1"-yl)ethyl)amino>but-2-enoate

Conditions
ConditionsYield
In methanol at 25℃; for 3h;100%
4-(2-AMINOETHYL)MORPHOLINE
2038-03-1

4-(2-AMINOETHYL)MORPHOLINE

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 3-<(2'-morpholinoethyl)amino>but-2-enoate

methyl 3-<(2'-morpholinoethyl)amino>but-2-enoate

Conditions
ConditionsYield
In methanol at 25℃; for 10h;100%
benzaldehyde
100-52-7

benzaldehyde

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

dimethyl 4-phenyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate
70677-78-0

dimethyl 4-phenyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate

Conditions
ConditionsYield
With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10h; Reagent/catalyst; Hantzsch Dihydropyridine Synthesis;100%
With ammonium acetate In ethanol at 60℃; for 0.5h; Catalytic behavior; Hantzsch Dihydropyridine Synthesis;98%
With ammonium acetate at 90℃; for 0.916667h; Hantzsch synthesis; Neat (no solvent);97%
methanol
67-56-1

methanol

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

3,3-bismethoxybutyric acid methyl ester
29267-46-7

3,3-bismethoxybutyric acid methyl ester

Conditions
ConditionsYield
With RuCl2-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)(benzonitrile)2; hydrogen at 50℃; under 76000.1 Torr; for 48h;100%
4-aminobutyrylaldehyde diethylacetal
6346-09-4

4-aminobutyrylaldehyde diethylacetal

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 3-<(4',4'-diethoxybutyl)amino>but-2-enoate

methyl 3-<(4',4'-diethoxybutyl)amino>but-2-enoate

Conditions
ConditionsYield
In methanol at 25℃; for 3h;100%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(E)-3-<2,4-dichloro-6-(phenylmethoxy)phenyl>-2-propenal
78443-74-0

(E)-3-<2,4-dichloro-6-(phenylmethoxy)phenyl>-2-propenal

methyl (E)-7-<2,4-dichloro-6-(phenylmethoxy)phenyl>-5-hydroxy-3-oxo-6-heptenoate
78443-77-3

methyl (E)-7-<2,4-dichloro-6-(phenylmethoxy)phenyl>-5-hydroxy-3-oxo-6-heptenoate

Conditions
ConditionsYield
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane100%
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane100%
With n-butyllithium; sodium hydride Yield given. Multistep reaction;
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(S)-3-hydroxybutyric acid methyl ester
53562-86-0

(S)-3-hydroxybutyric acid methyl ester

Conditions
ConditionsYield
With cat; hydrogen In methanol; dichloromethane at 25℃; under 77572.2 Torr; for 48h;100%
With (S)-BiphempRuBr2; hydrogen In methanol at 80℃; under 7600 Torr; for 1h;100%
With hydrogen; [RuCl2(Sax-4,4'-bis(3-diphenylphosphineestra...)(DMF)]n In methanol at 100℃; under 76000 Torr; for 1h; Catalytic hydrogenation;100%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

A

(S)-3-hydroxybutyric acid methyl ester
53562-86-0

(S)-3-hydroxybutyric acid methyl ester

B

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With Ru2Cl4-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt3; hydrogen In methanol at 35℃; under 76000.1 Torr; for 48h; Title compound not separated from byproducts;A 100%
B n/a
With <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3; hydrogen In methanol at 35℃; under 76000.1 Torr; for 48h; Title compound not separated from byproducts;A n/a
B 100%
With hydrogen; Ru(BICP)Br2 In methanol at 40 - 65℃; under 750.075 - 3750.38 Torr;A n/a
B 95%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
With cat; hydrogen In methanol; dichloromethane at 25℃; under 77572.2 Torr; for 48h;100%
With (R)-MeOBiphepRuBr2; hydrogen In methanol at 50℃; under 15200 Torr; for 48h;100%
With (S)-4,12-bis(diphenylphosphino)-<2.2>paracyclophane-Ru(II)bis(trifluoroacetate); hydrogen; tetra-(n-butyl)ammonium iodide In methanol; water at -5℃; under 2585.7 Torr; for 18h;100%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(1S,3R,5R,7R)-3-Chloro-10,10-dimethyl-3-phenyl-4-oxa-3λ4-selena-tricyclo[5.2.1.01,5]decane
156832-27-8

(1S,3R,5R,7R)-3-Chloro-10,10-dimethyl-3-phenyl-4-oxa-3λ4-selena-tricyclo[5.2.1.01,5]decane

2-[((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethyl)-phenyl-λ4-selanylidene]-3-oxo-butyric acid methyl ester

2-[((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethyl)-phenyl-λ4-selanylidene]-3-oxo-butyric acid methyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane for 1h; Ambient temperature;100%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

urea
57-13-6

urea

5-methoxycarbonyl-4-(4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one
205999-87-7

5-methoxycarbonyl-4-(4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With sulfuric acid; copper(l) chloride In methanol Biginelli Pyrimidone Synthesis; Reflux; Inert atmosphere;100%
With ytterbium(III) triflate at 100℃; for 0.333333h; Biginelli reaction;99%
With calcium chloride In ethanol for 2h; Biginelli reaction; Heating;98%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Cysteamine
60-23-1

Cysteamine

(Z)-3-(2-Mercapto-ethylamino)-but-2-enoic acid methyl ester
503616-48-6

(Z)-3-(2-Mercapto-ethylamino)-but-2-enoic acid methyl ester

Conditions
ConditionsYield
for 24h; Ambient temperature;100%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

rac-methylbenzylamine
618-36-0

rac-methylbenzylamine

(Z)-3-(1-Phenyl-ethylamino)-but-2-enoic acid methyl ester
374559-41-8

(Z)-3-(1-Phenyl-ethylamino)-but-2-enoic acid methyl ester

Conditions
ConditionsYield
In methanol for 12h; Heating;100%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

benzylamine
100-46-9

benzylamine

3-benzylaminobut-2-enoic acid methyl ester
72002-24-5

3-benzylaminobut-2-enoic acid methyl ester

Conditions
ConditionsYield
In methanol for 12h; Heating;100%
In methanol at 20℃; for 0.5h;95%
With calcium bistrifluoroacetate at 20℃; for 0.5h; chemoselective reaction;95%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(Z)-3-(2-Hydroxy-1-phenyl-ethylamino)-but-2-enoic acid methyl ester
374559-28-1

(Z)-3-(2-Hydroxy-1-phenyl-ethylamino)-but-2-enoic acid methyl ester

Conditions
ConditionsYield
In methanol for 12h; Heating;100%
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(Z)-3-((S)-2-Hydroxy-1-phenyl-ethylamino)-but-2-enoic acid methyl ester
476187-10-7

(Z)-3-((S)-2-Hydroxy-1-phenyl-ethylamino)-but-2-enoic acid methyl ester

Conditions
ConditionsYield
In methanol for 24h; Heating;100%
heptanal
111-71-7

heptanal

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

5-hydroxy-3-oxo-undecanoic acid methyl ester
869211-56-3

5-hydroxy-3-oxo-undecanoic acid methyl ester

Conditions
ConditionsYield
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.333333h;
Stage #3: heptanal In tetrahydrofuran; hexane at -78 - 20℃; for 1.08333h;
100%
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃;
Stage #2: With n-butyllithium In tetrahydrofuran at -78℃;
Stage #3: heptanal In tetrahydrofuran Further stages.;
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

isobutyraldehyde
78-84-2

isobutyraldehyde

5-hydroxy-6-methyl-3-oxo-heptanoic acid methyl ester
55848-84-5

5-hydroxy-6-methyl-3-oxo-heptanoic acid methyl ester

Conditions
ConditionsYield
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.333333h;
Stage #3: isobutyraldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 1.08333h;
100%
Stage #1: acetoacetic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -60 - 20℃; for 0.416667h; Weiler method; Inert atmosphere;
Stage #2: isobutyraldehyde In tetrahydrofuran; hexane at -60 - 20℃; for 4h; Weiler method; Inert atmosphere;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane Inert atmosphere;
95%
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃;
Stage #2: With n-butyllithium In tetrahydrofuran at -78℃;
Stage #3: isobutyraldehyde In tetrahydrofuran Further stages.;
(S)-2-(tert-butyldimethylsilyloxy)-1-phenylethylamine
120417-13-2

(S)-2-(tert-butyldimethylsilyloxy)-1-phenylethylamine

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(Z)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-but-2-enoic acid methyl ester
725250-70-4

(Z)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-but-2-enoic acid methyl ester

Conditions
ConditionsYield
In methanol for 24h; Heating;100%
In methanol
phenethyl azide
6926-44-9

phenethyl azide

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

3-phenethylamino-but-2-enoic acid methyl ester

3-phenethylamino-but-2-enoic acid methyl ester

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃;100%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Trimethylenediamine
109-76-2

Trimethylenediamine

3-[3-(2-methoxycarbonyl-1-methylvinylamino)-propylamino]but-2-enoic acid methyl ester

3-[3-(2-methoxycarbonyl-1-methylvinylamino)-propylamino]but-2-enoic acid methyl ester

Conditions
ConditionsYield
With silica-supported ferric hydrogensulfate/[Fe(HSO4)3*SiO2] In neat (no solvent) at 20℃; for 0.2h; regioselective reaction;100%
zirconium(IV) chloride at 20℃; for 0.25h;95%
With sulfated zirconia at 20℃; for 0.416667h;92%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 2-bromo-3-oxobutanoate
3600-18-8

methyl 2-bromo-3-oxobutanoate

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene at 20℃; for 2h; Inert atmosphere;100%
With N-Bromosuccinimide; toluene-4-sulfonic acid In dichloromethane at 20℃; for 0.416667h;94%
With ammonium cerium(IV) nitrate at 25 - 28℃; for 2.5h;87%
nonan-1-al
124-19-6

nonan-1-al

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

5-hydroxy-3-oxo-tridecanoic acid methyl ester

5-hydroxy-3-oxo-tridecanoic acid methyl ester

Conditions
ConditionsYield
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.333333h;
Stage #3: nonan-1-al In tetrahydrofuran; hexane at -78 - 20℃; for 1.08333h;
100%
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 5℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; mineral oil at 5℃; for 0.166667h;
Stage #3: nonan-1-al In tetrahydrofuran; mineral oil at 5 - 10℃; for 0.5h;
tetrakis(triphenylphosphine) palladium(0)
14221-01-3

tetrakis(triphenylphosphine) palladium(0)

trityl tetrafluoroborate
341-02-6

trityl tetrafluoroborate

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

bis(triphenylphosphine)(methyl acetylacetato)palladium(II) tetrafluoroborate
80583-72-8

bis(triphenylphosphine)(methyl acetylacetato)palladium(II) tetrafluoroborate

Conditions
ConditionsYield
In acetone; benzene (N2); a soln. of CPh3BF4 and methyl acetoacetate in acetone was added to a soln. of the Pd complex in benzene, the soln. was agitated for 48 h; recrystn. from acetone-ether; elem. anal.;100%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

benzyl halide

benzyl halide

2-benzyl-3-oxo-butyric acid methyl ester
3666-82-8

2-benzyl-3-oxo-butyric acid methyl ester

Conditions
ConditionsYield
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 25℃; for 1h; Inert atmosphere;
Stage #2: benzyl halide In tetrahydrofuran; mineral oil at 0℃;
100%
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;
Stage #2: benzyl halide In tetrahydrofuran; mineral oil at 20 - 40℃; Inert atmosphere;
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;
Stage #2: benzyl halide In tetrahydrofuran; mineral oil for 12h; Inert atmosphere; Reflux;
2-aminopyridine
504-29-0

2-aminopyridine

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one
1693-94-3

2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions
ConditionsYield
With bismuth(III) chloride at 100℃; for 3h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Green chemistry;100%
With trichlorophosphate
N-BOC-1,2-diaminoethane
57260-73-8

N-BOC-1,2-diaminoethane

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(Z)-methyl 3-((2-((tert.-butoxycarbonyl)amino)ethyl)amino)but-2-enoate
1240195-07-6

(Z)-methyl 3-((2-((tert.-butoxycarbonyl)amino)ethyl)amino)but-2-enoate

Conditions
ConditionsYield
With silica gel at 20℃; for 16h;100%
With silica gel In dichloromethane at 10 - 20℃; for 1h;127.9 g
With silica gel In dichloromethane at 10 - 20℃; for 1h;127.9 g

105-45-3Relevant articles and documents

Synthesis of methyl acetoacetate from acetone and dimethyl carbonate with alkali-promoted MgO catalysts

Wu, Dudu,Chen, Zhi

, p. 758 - 766 (2010)

The synthesis of methyl acetoacetate (MAA) by methoxycarbonylation of acetone with dimethyl carbonate (DMC) was carried out in the presence of MgO and alkali-promoted MgO catalysts. From among Li, Na, K, and Cs, potassium was found to be the most effective promoter to improve the activity of MgO. The effect of K/MgO with variable content of K was also investigated, and the individual catalysts were characterised by the XRD, BET, SEM, CO2-TPD, and in situ CO2 IR techniques. The results showed that the addition of a small amount of K (1.97 mass %) could promote MAA formation, but a higher K loading caused a decrease in the yield of MAA, which might result from particle agglomeration and the presence of stable potassium carbonates. In situ FTIR experiments of co-adsorbed reactants indicated that the reaction probably proceeded via abstraction of Hα from acetone by base sites.

-

Royals

, p. 489 (1948)

-

Asymmetric Aerobic Epoxidation of Unfunctionalized Olefins Catalyzed by Optically Active α-Alkoxycarbonyl-β-ketoiminato Manganese(III) Complexes

Mukaiyama, Teruaki,Yamada, Tohru,Nagata, Takushi,Imagawa, Kiyomi

, p. 327 - 330 (1993)

Optically active N,N'-ethylenebis(α-alkoxycarbonyl-β-ketoimine) was found to be a new class of effective ligand of manganese(III) complex catalyst for the asymmetric aerobic epoxidation of simple olefins, such as 1,2-dihydronaphthalene derivatives, to afford the corresponding optically active epoxides with good to high enantioselectivities.

New method of zinc activation by electrochemistry: synthetic applications to the Blaise reaction

Zylber, N.,Zylber, J.,Rollin, Y.,Dunach, E.,Perichon, J.

, p. 1 - 4 (1993)

A new electrochemical zinc metal activation method based on the cathodic reduction of a catalytic amount of zinc bromide in the presence of a zinc anode is described.This procedure is applied to the coupling of α-bromoesters with nitriles, and affords β-ketoesters in good yield.

Carbonylation of chloroacetone to methyl acetoacetate

Lapidus,Eliseev,Bondarenko,Sizan,Ostapeako

, p. 2239 - 2241 (2001)

Methyl acetoacetate was prepared by the selective carbonylation of chloroacetone in the presence of a homogeneous palladium catalyst at 100 °C and under a CO pressure of 1.5 MPa.

A NEW PREPARATIVE METHOD FOR 1,3-DICARBONYL COMPOUNDS BY THE REGIOSELECTIVE OXIDATION OF α,β-UNSATURATED CARBONYL COMPOUNDS, CATALYZED BY PdCl2 USING HYDROGENPEROXIDES AS THE REOXIDANT OF Pd0

Tsuji, Jiro,Nagashima, Hideo,Hori, Kimihiko

, p. 257 - 260 (1980)

α,β-Unsaturated esters and ketones are oxidized regioselectively to give β-keto esters and 1,3-diketones in good yields in aqueous acetic acid using Na2PdCl4 as the catalyst and t-butyl hydroperoxide or hydrogen peroxide as the reoxidant of Pd0.

-

Eisenmann et al.

, p. 2102 (1961)

-

Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions

Yuan, Yong,Li, Liang-Sen,Zhang, Lin,Wang, Feng,Jiang, Lin,Zuo, Lin,Wang, Qi,Hu, Jian-Guo,Lei, Aiwen

supporting information, p. 2768 - 2771 (2021/03/23)

An electrochemical oxidative cross-coupling reaction between 2.5-substituted-pyrazolin-5-ones and ammonium thiocyanate has been developed, which resulted in a series of unprecedented cross-coupling products under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions. It is worth noting that since the resulting cross-coupling products are nearly insoluble in MeCN, the pure product could be afforded without silica gel column purification. In addition, the prepared ammonium oxides are versatile building blocks for synthesizing functionalized pyrazole derivatives.

Method for synthesizing methyl acetoacetate

-

Paragraph 0014-0031, (2020/08/09)

The invention relates to a novel method for synthesizing methyl acetoacetate, which comprises the following steps: using methyl crotonate as a raw material, oxygen or air as an oxidant and nickel chloride and organic amine as catalysts, carrying out oxidation reaction to directly prepare methyl acetoacetate from methyl crotonate. Compared with the existing process for preparing methyl acetoacetate, the method has the advantages that the use of a strong acid catalyst in a diketene route is avoided, and the methyl acetoacetate synthesis method which is low in cost and environment-friendly and does not need noble metal palladium is provided.

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