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542-08-5

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542-08-5 Usage

Chemical Properties

Colourless Liquid

Uses

Different sources of media describe the Uses of 542-08-5 differently. You can refer to the following data:
1. Isopropyl acetoacetate (IPAA) is used as intermediate for chemical synthesis. Product Data Sheet
2. Isopropyl acetoacetate is used as an intermediate for the manufacturing of agrochemicals and pharmaceutical products such as isradipine.

Application

Isopropyl acetoacetate can be used as a reactant to synthesize:Isopropyl 2-acetyl-3-phenyl-2-propenoate via Knoevenagel reaction in the presence of Ti(O-i-Pr)4.Substituted 1,4-dihydropyridines by reacting with cinnamaldehydes and primary amines.5-Isopropoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione via Biginelli reaction with benzaldehyde and thiourea.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 225, 1961 DOI: 10.1021/jo01060a055

Check Digit Verification of cas no

The CAS Registry Mumber 542-08-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 2 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 542-08:
(5*5)+(4*4)+(3*2)+(2*0)+(1*8)=55
55 % 10 = 5
So 542-08-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H12O3/c1-5(2)10-7(9)4-6(3)8/h5H,4H2,1-3H3

542-08-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (I0826)  Isopropyl Acetoacetate  >97.0%(GC)

  • 542-08-5

  • 25g

  • 150.00CNY

  • Detail
  • TCI America

  • (I0826)  Isopropyl Acetoacetate  >97.0%(GC)

  • 542-08-5

  • 500g

  • 1,150.00CNY

  • Detail

542-08-5Synthetic route

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

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

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With sodium acetate for 24h; Reflux;98%
Esterification;92%
In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 3h;55%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane at 50 - 90℃; for 2h; Reagent/catalyst; Temperature;95.5%
With triethylamine at 95℃; for 3h;89.6%
With sodium acetate at 115℃; for 2.5h;86%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

titanium(IV)isopropoxide
546-68-9

titanium(IV)isopropoxide

A

isopropyl E-5-hydroxy-3-oxo-7-phenyl-6-heptenoate

isopropyl E-5-hydroxy-3-oxo-7-phenyl-6-heptenoate

B

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
In dichloromethaneA 88%
B n/a
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In toluene for 5h; Reflux;87%
With iodine In toluene for 7h; Heating;63%
niobium(V) oxide In toluene for 8h; Heating;63%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide for 0.0116667h; Reagent/catalyst; Microwave irradiation;83%
With Prussian blue In toluene for 0.183333h; Microwave irradiation;82%
With silver trifluoromethanesulfonate In toluene at 110℃; for 10h;77%
With iodine In toluene for 6h; Ionic liquid; Reflux;68%
isopropyl 4-bromo-3-oxobutanoate
134969-44-1

isopropyl 4-bromo-3-oxobutanoate

triphenylphosphine
603-35-0

triphenylphosphine

A

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

B

(3-Isopropoxycarbonyl-2-oxopropyl)triphenylphosphonium bromide

(3-Isopropoxycarbonyl-2-oxopropyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In benzene for 24h; Ambient temperature; Yields of byproduct given;A n/a
B 82.9%
2,4-oxetanedione
15159-48-5

2,4-oxetanedione

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With triethylamine for 5h; Ambient temperature;77.5%
Isopropyl acetate
108-21-4

Isopropyl acetate

methyl (2S)-N-tritylaziridine-2-carboxylate
75154-68-6

methyl (2S)-N-tritylaziridine-2-carboxylate

A

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

B

(4S)-3-oxo-4,5-(N-triphenylmethylepimino)pentanoic acid isopropyl ester
236742-98-6

(4S)-3-oxo-4,5-(N-triphenylmethylepimino)pentanoic acid isopropyl ester

Conditions
ConditionsYield
Stage #1: Isopropyl acetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Metallation;
Stage #2: methyl (2S)-N-tritylaziridine-2-carboxylate In tetrahydrofuran; hexane at -78℃; for 12h; Claisen condensation;
A n/a
B 70%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

acetyl chloride
75-36-5

acetyl chloride

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
Stage #1: cycl-isopropylidene malonate; acetyl chloride With pyridine In dichloromethane at 0 - 20℃; for 2h;
Stage #2: isopropyl alcohol for 2h; Reflux;
65%
Isopropyl acetate
108-21-4

Isopropyl acetate

isopropylmagnesium chloride
1068-55-9

isopropylmagnesium chloride

A

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

B

3-hydroxy-3,4-dimethyl-valeric acid isopropyl ester
54074-71-4

3-hydroxy-3,4-dimethyl-valeric acid isopropyl ester

Conditions
ConditionsYield
With diethyl ether
Isopropyl acetate
108-21-4

Isopropyl acetate

sodium isopropylate
683-60-3

sodium isopropylate

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
Geschwindigkeit;
Isopropyl acetate
108-21-4

Isopropyl acetate

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With sodium isopropylate at 87℃;
With diethyl ether; ammonia; sodium amide
With sodium
(i) LiNH2, liq. NH3, (ii) Ph2CO; Multistep reaction;
Acetoacetylfluorid
2343-88-6

Acetoacetylfluorid

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With triethylamine In diethyl ether
1-<(Carboisopropoxy)methylthio>ethylidenyldimethylammonium Iodide
73200-00-7

1-<(Carboisopropoxy)methylthio>ethylidenyldimethylammonium Iodide

1-<(Carboethoxy)methylthio>pentylidenyldimethylammonium Iodide
73200-01-8

1-<(Carboethoxy)methylthio>pentylidenyldimethylammonium Iodide

A

Ethyl 3-oxoheptanoate
7737-62-4

Ethyl 3-oxoheptanoate

B

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

C

ethyl acetoacetate
141-97-9

ethyl acetoacetate

D

Isopropyl 3-Oxoheptanoate
73200-02-9

Isopropyl 3-Oxoheptanoate

Conditions
ConditionsYield
With bis [3-dimethyl-amino-1-propyl] phenyl phosphine In acetonitrile Mechanism; Heating;
isopropyl alcohol
67-63-0

isopropyl alcohol

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

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With triethylamine Heating;
isopropyl 4-bromo-3-oxobutanoate
134969-44-1

isopropyl 4-bromo-3-oxobutanoate

triphenylphosphine
603-35-0

triphenylphosphine

A

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

B

(3-Isopropoxycarbonyl-2-oxopropyl)triphenylphosphonium bromide

(3-Isopropoxycarbonyl-2-oxopropyl)triphenylphosphonium bromide

C

((Z)-2-Bromo-3-isopropoxycarbonyl-allyl)-triphenyl-phosphonium; bromide

((Z)-2-Bromo-3-isopropoxycarbonyl-allyl)-triphenyl-phosphonium; bromide

D

(3-Bromo-1-isopropoxycarbonyl-2-oxo-propyl)-triphenyl-phosphonium; bromide

(3-Bromo-1-isopropoxycarbonyl-2-oxo-propyl)-triphenyl-phosphonium; bromide

Conditions
ConditionsYield
In benzene for 24h; Product distribution; Ambient temperature; various solvents;
In chloroform-d1 Ambient temperature;A 18 % Spectr.
B 60.5 % Spectr.
C n/a
D n/a
5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
85920-63-4

5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
In toluene Heating;
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

titanium(IV)isopropoxide
546-68-9

titanium(IV)isopropoxide

A

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

B

(S,E)-5-hydroxy-3-oxo-7-phenyl-6-heptenoic acid isopropyl ester

(S,E)-5-hydroxy-3-oxo-7-phenyl-6-heptenoic acid isopropyl ester

C

(R)-(E)-isopropyl 5-hydroxy-7-phenyl-3-oxo-6-heptenoate

(R)-(E)-isopropyl 5-hydroxy-7-phenyl-3-oxo-6-heptenoate

Conditions
ConditionsYield
With (S)-[1,1']-binaphthalenyl-2,2'-diol In dichloromethane at 20℃; for 24h; Title compound not separated from byproducts;
S-phenyl thioacetate
934-87-2

S-phenyl thioacetate

S-phenyl 3-oxobutanethioate
40053-29-0

S-phenyl 3-oxobutanethioate

isopropyl alcohol
67-63-0

isopropyl alcohol

A

Isopropyl acetate
108-21-4

Isopropyl acetate

B

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With silver trifluoroacetate In chloroform for 3h;
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

Conditions
ConditionsYield
With ammonium acetate In ethanol for 24h; Reflux;100%
With ammonia In water at 25℃; for 3h; Temperature; Reagent/catalyst;91.7%
With ammonium hydroxide; ammonium acetate at -5 - 5℃; for 18h;86%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

isopropyl ester of (R)-3-hydroxybutanoic acid
87128-49-2

isopropyl ester of (R)-3-hydroxybutanoic acid

Conditions
ConditionsYield
With hydrogen; C50H44Cl2N2O8P4Ru(4-)*Zr(4+) In methanol at 20℃; under 72402.6 Torr; for 20h; Product distribution / selectivity;100%
With C50H46Cl2N2O2P2Ru; hydrogen In methanol at 50℃; under 30003 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Autoclave; enantioselective reaction;99%
With hydrogen; [(R)-BINAP]RuBr2 In methanol at 23 - 30℃; under 55480 Torr; for 34h;93 % Chromat.
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

2-[1-(2-Chloro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid isopropyl ester
139471-96-8

2-[1-(2-Chloro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid isopropyl ester

Conditions
ConditionsYield
With piperdinium acetate In isopropyl alcohol at 45 - 55℃;100%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

isopropyl 2-((dimethylamino)methylene)-3-oxobutanoate
329363-90-8

isopropyl 2-((dimethylamino)methylene)-3-oxobutanoate

Conditions
ConditionsYield
at 20℃;100%
at 20℃;100%
at 20℃;100%
In chloroform for 1h; Heating;
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

methyl iodide
74-88-4

methyl iodide

rac-isopropyl 2-methyl-3-oxobutanoate
919771-62-3

rac-isopropyl 2-methyl-3-oxobutanoate

Conditions
ConditionsYield
With potassium carbonate at 0 - 40℃; for 3h;99%
Stage #1: isopropyl acetoacetate With potassium carbonate In acetone for 0.0833333h; Inert atmosphere;
Stage #2: methyl iodide In acetone for 18h; Inert atmosphere; Reflux;
81%
Stage #1: isopropyl acetoacetate With potassium carbonate In acetone for 0.0833333h; Inert atmosphere;
Stage #2: methyl iodide In acetone for 18h; Inert atmosphere; Reflux;
81%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

2-aminoacetophenone
551-93-9

2-aminoacetophenone

iso-propyl 2,4-dimethylquinoline-3-carboxylate

iso-propyl 2,4-dimethylquinoline-3-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 80℃; for 12h; Reagent/catalyst; Friedlaender Quinoline Synthesis; Schlenk technique;99%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

benzaldehyde
100-52-7

benzaldehyde

urea
57-13-6

urea

(±)-isopropyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate

(±)-isopropyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 1.3h; Biginelli reaction;98%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 2h; Biginelli pyrimidine synthesis;96%
With silica-supported Cu(I) In ethanol for 5h; Biginelli pyrimidine synthesis; Reflux;93%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

urea
57-13-6

urea

5-isopropoxycarbonyl-4-(4'-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

5-isopropoxycarbonyl-4-(4'-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 2h; Biginelli reaction;98%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 2h; Biginelli pyrimidine synthesis;94%
With Amberlyst 15-supported ytterbium(III) reagent at 120℃; for 48h; Biginelli reaction;
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

urea
57-13-6

urea

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

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

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 1.3h; Biginelli reaction;98%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 2h; Biginelli pyrimidine synthesis;94%
With hexaaquaaluminium(III) tetrafluoroborate In acetonitrile for 20h; Biginelli pyrimidine synthesis; Reflux;83%
With Amberlyst 15-supported ytterbium(III) reagent at 120℃; for 48h; Biginelli reaction;75%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

urea
57-13-6

urea

5-isopropoxycarbonyl-6-methyl-4-(3-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione

5-isopropoxycarbonyl-6-methyl-4-(3-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione

Conditions
ConditionsYield
With 1-butyl-3-carboxymethyl-benzotriazolium trifluoroacetate In neat (no solvent) at 90℃; for 0.666667h; Biginelli Pyrimidone Synthesis;98%
vinyl acetate
108-05-4

vinyl acetate

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

isopropyl 1,3,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

isopropyl 1,3,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With isopropyl alcohol In water at 60℃; for 48h; Biginelli Pyrimidone Synthesis; Enzymatic reaction;98%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

zinc(II) chloride
7646-85-7

zinc(II) chloride

2C7H11O3(1-)*Zn(2+)

2C7H11O3(1-)*Zn(2+)

Conditions
ConditionsYield
Stage #1: isopropyl acetoacetate With sodium methylate In isopropyl alcohol at 80℃; for 1h;
Stage #2: zinc(II) chloride In isopropyl alcohol at 70 - 90℃; for 4.5h;
98%
oct-1-ene
111-66-0

oct-1-ene

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

isopropyl 2-acetyl-3-methylnonanoate

isopropyl 2-acetyl-3-methylnonanoate

Conditions
ConditionsYield
With [Ir(cod)2]SbF6; 2,2'-bis(diphenylphosphino)biphenyl for 24h; Reflux; diastereoselective reaction;98%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

acetyl chloride
75-36-5

acetyl chloride

isopropyl diacetylacetate
365212-62-0

isopropyl diacetylacetate

Conditions
ConditionsYield
With pyridine; magnesium chloride In dichloromethane at 0 - 20℃; for 16h;97%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

thiourea
17356-08-0

thiourea

isopropyl 2-amino-4-methylthiazole-5-carboxylate

isopropyl 2-amino-4-methylthiazole-5-carboxylate

Conditions
ConditionsYield
With erythrosine B; oxygen In acetonitrile at 20℃; for 8h; Irradiation; Green chemistry;97%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

5-Bromo-1H-indole-2,3-dione
87-48-9

5-Bromo-1H-indole-2,3-dione

isopropyl (R)-4-(5-bromo-3-hydroxy-2-oxoindolin-3-yl)-3-oxobutanoate

isopropyl (R)-4-(5-bromo-3-hydroxy-2-oxoindolin-3-yl)-3-oxobutanoate

Conditions
ConditionsYield
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((R)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea In tetrahydrofuran at 4℃; for 96h; Aldol Addition; enantioselective reaction;97%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

anthranilic acid amide
28144-70-9

anthranilic acid amide

2,2-dimethyl-2,3-dihydro-1H-quinazolin-4-one
77726-78-4

2,2-dimethyl-2,3-dihydro-1H-quinazolin-4-one

Conditions
ConditionsYield
With Candida antarctica lipase B In hexane; water at 50℃; for 40h; Enzymatic reaction;97%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

iso-propyl (S)-(+)-3-hydroxybutyrate
111970-49-1

iso-propyl (S)-(+)-3-hydroxybutyrate

Conditions
ConditionsYield
With yeast Saccharomyces cerevisiae; water In Petroleum ether Ambient temperature;96%
With hydrogen In isopropyl alcohol at 80℃; under 15001.5 Torr; for 10h; enantioselective reaction;96.5%
With dichloro(benzene)ruthenium(II) dimer; C49H52O2P2; hydrogen In methanol at 80℃; under 38002.6 Torr; for 12h; optical yield given as %ee; enantioselective reaction;
With D-Glucose; cobalt(II); BaSDR1 reductase variant Q139G; NADH In aq. phosphate buffer at 35℃; pH=7.5; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;n/a
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

urea
57-13-6

urea

5-isopropoxycarbonyl-4-(4'-fluorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

5-isopropoxycarbonyl-4-(4'-fluorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 2h; Biginelli reaction;96%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 2h; Biginelli pyrimidine synthesis;94%
With Amberlyst 15-supported ytterbium(III) reagent at 120℃; for 48h; Biginelli reaction;
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

urea
57-13-6

urea

5-isopropoxycarbonyl-6-methyl-4-(4'-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one

5-isopropoxycarbonyl-6-methyl-4-(4'-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 3h; Biginelli reaction;96%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 4h; Biginelli pyrimidine synthesis;90%
With Amberlyst 15-supported ytterbium(III) reagent at 120℃; for 48h; Biginelli reaction;
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

urea
57-13-6

urea

(±)-isopropyl 4-(2-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
312596-19-3

(±)-isopropyl 4-(2-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 1.3h; Biginelli reaction;96%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 2h; Biginelli pyrimidine synthesis;96%
With zinc(II) chloride In tetrahydrofuran at 70℃; for 12h; Biginelli Pyrimidone Synthesis;92%
diphenyl(trifluoromethanesulfonato)-λ3-iodane

diphenyl(trifluoromethanesulfonato)-λ3-iodane

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

(Z)-isopropyl 3-phenoxybut-2-enoate
1613614-14-4

(Z)-isopropyl 3-phenoxybut-2-enoate

Conditions
ConditionsYield
With copper(l) iodide; lithium carbonate In 1,4-dioxane at 70℃; for 60h; Inert atmosphere; Sealed tube; regioselective reaction;96%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

isopropyl 3-aminocrotonate
40100-28-5

isopropyl 3-aminocrotonate

Conditions
ConditionsYield
With ammonia In dichloromethane95%
With ammonia at 10℃;89%
With ammonia In ethanol
tryptamine
61-54-1

tryptamine

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

3-phenyl-propenal
104-55-2

3-phenyl-propenal

(2S,12bS)-isopropyl 4-methyl-2-phenyl-1,2,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine-3-carboxylate
1225230-86-3

(2S,12bS)-isopropyl 4-methyl-2-phenyl-1,2,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine-3-carboxylate

Conditions
ConditionsYield
Stage #1: isopropyl acetoacetate; 3-phenyl-propenal With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In toluene at -15℃; for 24h; Inert atmosphere;
Stage #2: tryptamine With benzoic acid In toluene at 50℃; for 24h; optical yield given as %ee; enantioselective reaction;
95%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

C22H29NO4

C22H29NO4

Conditions
ConditionsYield
With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10h; Hantzsch Dihydropyridine Synthesis;95%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

C22H29NO5

C22H29NO5

Conditions
ConditionsYield
With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10h; Hantzsch Dihydropyridine Synthesis;95%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

urea
57-13-6

urea

Isopropyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
131275-78-0

Isopropyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With polyphosphate ester for 0.00833333h; Cyclization; Biginelli condensation; Irradiation;94%
With polyphosphonate ester In tetrahydrofuran for 24h; Biginelli cyclocondensation; Heating;94%
With ytterbium(III) triflate In toluene at 100℃; Biginelli Pyrimidone Synthesis;
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

urea
57-13-6

urea

5-isopropoxycarbonyl-6-methyl-4-(3-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione

5-isopropoxycarbonyl-6-methyl-4-(3-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione

Conditions
ConditionsYield
With 1-butyl-3-carboxymethyl-benzotriazolium trifluoroacetate In neat (no solvent) at 90℃; for 0.666667h; Biginelli Pyrimidone Synthesis;94%
With Amberlyst 15-supported ytterbium(III) reagent at 120℃; for 48h; Biginelli reaction;73%

542-08-5Relevant articles and documents

Enantioselective aldol-type reaction using diketene

Kawase, Takahiro,Takizawa, Shinobu,Jayaprakash, Doss,Sasai, Hiroaki

, p. 4487 - 4492 (2004)

An aldol-type reaction catalyzed by a Ti-(S)-BINOL complex using with a diketene as substrate is described herein. The complex derived from 1.0 molar equivalent of Ti(O-i-Pr)4 and 2.0 molar equivalents of (S)-BINOL gave (5)-isopropyl 5-hydroxy-7-phenyl-3-oxo-6-heptenoate with high enantioselectivity.

Br?nsted acidic cellulose-PO3H: An efficient catalyst for the chemoselective synthesis of fructones and trans-esterification via condensation of acetoacetic esters with alcohols and diols

Naikwadi, Dhanaji R.,Singh, Amravati S.,Biradar, Ankush V.

, (2021/10/04)

Cellulose is the most abundant organic source and has expedient a great deal of interest as renewable and emerged as sustainable feedstock. The functionalization of cellulose as designed catalytic system intriguing furnished to the production of fine chemicals. Herein, we synthesized an environmental friendly solid acid catalyst by functionalizing cellulose with phosphoric acid (PO3H). The successful functionalization of cellulose with PO3H was confirmed by 31P NMR, ICP-OES, FE-SEM, and XPS analysis. ICP-OES revealed the presence of phosphorus content of ~1.0 wt. % on the catalyst's surface while elemental mapping by FESEM and XPS shows a uniform distribution of phosphorus over the material. The synthesized solid acid catalyst was utilized for condensation of diols with acetoacetic esters in solvent-free conditions to synthesize fine chemicals. The present approach not only circumvented the one-step protection and other products but more fascinatingly provided trans-esterification of acetoacetic esters with diols and n-alcohols. The catalyst was successfully used for chemoselective protection on ethyl acetoacetate with 1, 2 diols to essential fructone molecule with ~100% conversion and 99% selectivity. The results suggested that the catalyst has the advantage over commercial solid acid heterogeneous and homogeneous catalysts.

Nimodipine impurity IV reference substance as well as preparation method and application thereof

-

Paragraph 0051-0052, (2020/11/22)

The invention discloses a nimodipine impurity IV reference substance and a preparation method thereof. The method includes the steps that diketene, ethyl alcohol and triethylamine are taken and addedinto a container to be heated and cooled, reaction liquid is washed with water, washing liquid is discarded, anhydrous sodium sulfate is added and placed overnight, filtrate is obtained after filtration, ammonia gas is introduced into the filtrate until the filtrate is saturated, and the nimodipine impurity IV reference substance is obtained; and after the reaction is finished, m-nitrobenzaldehyde, methoxyethyl acetoacetate and ethanol are added, heating refulx is performed, the mixture is cooled and filtered, the solvent is removed through volatilization in a water bath to obtain a yellow viscous liquid, and recrystallization is carried out to obtain a yellow acicular crystal, namely the nimodipine impurity IV reference substance. The invention also discloses an application of the nimodipine impurity IV reference substance in nimodipine tablet consistency evaluation. According to the preparation method, the impurity IV can be prepared in a general analysis laboratory, special preparation equipment is not needed, the operation is simple, the purity of the obtained impurity reference substance can reach 98.4%, the purity requirement of the reference substance is met, and the preparation method can be used for consistency evaluation of the variety.

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