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592-20-1 Usage

Chemical Properties

Clear pale yellow to amber liquid

Uses

Acetoxyacetone is an building block in the synthesis of various pharmaceutical and organic compounds.

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 4263, 1992 DOI: 10.1021/jo00041a036

Purification Methods

Distil it in a vacuum, then redistil it at atmospheric pressure. It is miscible with H2O, but is slowly decomposed by it. Store it in a dry atmosphere. The 2,4-dinitrophenylhydrazone has m 115-115.5o (from CHCl3/hexane). [Perkin Jr J Chem Soc 59 789 1891, Reich & Samuels J Org Chem 21 68 1956, Nef Justus Liebigs Ann Chem 335 260 1904, Beilstein 2 IV 297.]

Check Digit Verification of cas no

The CAS Registry Mumber 592-20-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 2 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 592-20:
(5*5)+(4*9)+(3*2)+(2*2)+(1*0)=71
71 % 10 = 1
So 592-20-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O3/c1-4(6)3-8-5(2)7/h3H2,1-2H3

592-20-1 Well-known Company Product Price

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  • Alfa Aesar

  • (H31346)  Acetoxyacetone, 97%   

  • 592-20-1

  • 10ml

  • 978.0CNY

  • Detail
  • Alfa Aesar

  • (H31346)  Acetoxyacetone, 97%   

  • 592-20-1

  • 50ml

  • 3642.0CNY

  • Detail

592-20-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Acetoxyacetone

1.2 Other means of identification

Product number -
Other names 2-oxopropyl acetate

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:592-20-1 SDS

592-20-1Synthetic route

acetic anhydride
108-24-7

acetic anhydride

hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
With tetrakis(triphenylphosphineoxide)dioxouranium(VI) perchlorate In dichloromethane-d2 at 22℃; for 2.5h;99%
sodium acetate
127-09-3

sodium acetate

chloroacetone
78-95-5

chloroacetone

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
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;
2-methylglycidol
872-30-0

2-methylglycidol

lead(IV) tetraacetate
546-67-8

lead(IV) tetraacetate

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
In benzene for 2h; Inert atmosphere; Reflux; regioselective reaction;91%
acetic acid
64-19-7

acetic acid

acetone
67-64-1

acetone

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
With tert.-butylhydroperoxide; tetrabutylammomium bromide In acetone at 120℃; under 33753.4 Torr; for 0.5h; Inert atmosphere; Microwave irradiation;88%
3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

pentan-3-one
96-22-0

pentan-3-one

A

Acetol acetate
592-20-1

Acetol acetate

B

1-methyl-2-oxobutyl acetate
2983-05-3

1-methyl-2-oxobutyl acetate

Conditions
ConditionsYield
In acetone Heating; Yields of byproduct given;A n/a
B 64.6%
3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

cyclohexanone
108-94-1

cyclohexanone

A

Acetol acetate
592-20-1

Acetol acetate

B

2-acetoxycyclohexanone
17472-04-7

2-acetoxycyclohexanone

Conditions
ConditionsYield
In acetone Heating;A n/a
B 57.6%
methanol
67-56-1

methanol

Acetyl(1-chlor-1-methylethyl)peroxid
123775-21-3

Acetyl(1-chlor-1-methylethyl)peroxid

A

Acetol acetate
592-20-1

Acetol acetate

B

Acetyl(1-methoxy-1-methylethyl)peroxid
123775-22-4

Acetyl(1-methoxy-1-methylethyl)peroxid

Conditions
ConditionsYield
With sodium hydrogencarbonate In chloroform-d1 at 0℃; for 20h; Yields of byproduct given;A n/a
B 57%
3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

cyclopentanone
120-92-3

cyclopentanone

A

Acetol acetate
592-20-1

Acetol acetate

B

2-acetoxycyclopentanone
52789-75-0

2-acetoxycyclopentanone

Conditions
ConditionsYield
In acetone Heating;A n/a
B 54.3%
3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

butanone
78-93-3

butanone

A

3-acetoxy-2-butanone
4906-24-5

3-acetoxy-2-butanone

B

Acetol acetate
592-20-1

Acetol acetate

C

1-acetoxybutan-3-one
10150-87-5

1-acetoxybutan-3-one

D

2-oxobutyl acetate
1575-57-1

2-oxobutyl acetate

Conditions
ConditionsYield
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
100-41-4

ethylbenzene

3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

A

Acetol acetate
592-20-1

Acetol acetate

B

1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

C

1-phenylethyl acetate
93-92-5, 50373-55-2

1-phenylethyl acetate

D

acetophenone
98-86-2

acetophenone

Conditions
ConditionsYield
In acetone for 48h; Ambient temperature; Further byproducts given;A n/a
B 36%
C 14 % Chromat.
D 50%
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

A

Acetol acetate
592-20-1

Acetol acetate

B

3-Acetoxy-3-methyl-2-butanon
10235-71-9

3-Acetoxy-3-methyl-2-butanon

C

1-(acetyloxy)-3-methyl-2-butanone
36960-07-3

1-(acetyloxy)-3-methyl-2-butanone

Conditions
ConditionsYield
In acetone Heating; Yields of byproduct given;A n/a
B 43.6%
C n/a
In acetone Heating; Yield given. Yields of byproduct given;
3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

A

methanol
67-56-1

methanol

B

acetic acid methyl ester
79-20-9

acetic acid methyl ester

C

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
With di-isopropyl ether In acetone at 22℃; for 6h; Product distribution; Mechanism;A 12.1%
B 38.4%
C 11.8%
3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

2-Pentanone
107-87-9

2-Pentanone

A

Acetol acetate
592-20-1

Acetol acetate

B

4-(acetyloxy)-2-pentanone
55577-75-8

4-(acetyloxy)-2-pentanone

C

1-(acetyloxy)-2-pentanone
68113-53-1

1-(acetyloxy)-2-pentanone

D

(-)-1-Ethyl-2-oxopropyl acetate
20510-66-1

(-)-1-Ethyl-2-oxopropyl acetate

Conditions
ConditionsYield
In acetone Heating; Yields of byproduct given;A n/a
B n/a
C n/a
D 35.9%
In acetone Heating; Yield given. Yields of byproduct given;
3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

2,4-dimethylpentan-3-one
565-80-0

2,4-dimethylpentan-3-one

A

Acetol acetate
592-20-1

Acetol acetate

B

2-acetoxy-2,4-dimethyl-pentan-3-one
21980-75-6

2-acetoxy-2,4-dimethyl-pentan-3-one

Conditions
ConditionsYield
In acetone Heating; Yields of byproduct given;A n/a
B 32%
methanol
67-56-1

methanol

Allyl acetate
591-87-7

Allyl acetate

A

1,1,3-trimethoxypropane
14315-97-0

1,1,3-trimethoxypropane

B

3-acetoxypropanal
18545-28-3

3-acetoxypropanal

C

Acetol acetate
592-20-1

Acetol acetate

D

3-acetoxy-1,1-dimethoxy-propane
143056-89-7

3-acetoxy-1,1-dimethoxy-propane

Conditions
ConditionsYield
With disodium hydrogenphosphate Product distribution; hexamethylphosphoric triamide;A 16%
B 3%
C 11%
D 28%
3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

acetone
67-64-1

acetone

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
Heating;26.1%
Mechanism; Heating; other substrates, other ketones, or mixtures of ketones;26.1%
2,5-dimethoxy-2,5-dimethyl-1,4-dioxane
7504-90-7

2,5-dimethoxy-2,5-dimethyl-1,4-dioxane

acetic anhydride
108-24-7

acetic anhydride

A

acetic acid methyl ester
79-20-9

acetic acid methyl ester

B

Acetol acetate
592-20-1

Acetol acetate

2,5-dimethoxy-2,5-dimethyl-1,4-dioxane
7504-90-7

2,5-dimethoxy-2,5-dimethyl-1,4-dioxane

acetyl chloride
75-36-5

acetyl chloride

A

acetic acid methyl ester
79-20-9

acetic acid methyl ester

B

Acetol acetate
592-20-1

Acetol acetate

3-chloroacetyl acetone
7660-21-1

3-chloroacetyl acetone

potassium acetate
127-08-2

potassium acetate

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
With ethanol
acetic anhydride
108-24-7

acetic anhydride

chloroacetone
78-95-5

chloroacetone

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
at 140 - 150℃;
propargyl alcohol
107-19-7

propargyl alcohol

acetic acid
64-19-7

acetic acid

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
at 55 - 65℃; in Gegenwart eines durch Erhitzen von HgO mit (C2H5)2O+BF3 und wenig Trichloressigsaeure in Methanol dargestellten Katalysators;
at 55 - 65℃; in Gegenwart eines aus HgO, Borfluorid-aetherat, Methanol und Trichloressigsaeure hergestellten Katalysators;
With boron trifluoride diethyl etherate; mercury(II) oxide
acetic acid
64-19-7

acetic acid

chloroacetone
78-95-5

chloroacetone

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
at 140 - 150℃;
sodium acetate
127-09-3

sodium acetate

acetic acid
64-19-7

acetic acid

1-bromoacetone
598-31-2

1-bromoacetone

Acetol acetate
592-20-1

Acetol acetate

potassium acetate
127-08-2

potassium acetate

chloroacetone
78-95-5

chloroacetone

Acetol acetate
592-20-1

Acetol acetate

acetone
67-64-1

acetone

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
With lead(IV) acetate; acetic acid
potassium acetate
127-08-2

potassium acetate

1-bromoacetone
598-31-2

1-bromoacetone

Acetol acetate
592-20-1

Acetol acetate

2-chloropropanal
683-50-1

2-chloropropanal

sodium acetate
127-09-3

sodium acetate

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
In acetic acid Heating;
N-isopropyliden-cyclohexyl amine
6407-36-9

N-isopropyliden-cyclohexyl amine

acetic anhydride
108-24-7

acetic anhydride

Acetol acetate
592-20-1

Acetol acetate

Conditions
ConditionsYield
(i) LDA, Et2O, (ii) air, (iii) /BRN= 385737/; Multistep reaction;
Conditions
ConditionsYield
In acetic anhydride; acetic acid
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

A

Acetol acetate
592-20-1

Acetol acetate

B

4-(acetyloxy)-3,3-dimethyl-2-butanone
72816-02-5

4-(acetyloxy)-3,3-dimethyl-2-butanone

C

acetic acid 3,3-dimethyl-2-oxobutyl ester
38559-25-0

acetic acid 3,3-dimethyl-2-oxobutyl ester

Conditions
ConditionsYield
In acetone Heating; Yield given. Yields of byproduct given;
Acetol acetate
592-20-1

Acetol acetate

4-((4-(6-methoxypyridin-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-N-(piperidin-4-yl)benzamide

4-((4-(6-methoxypyridin-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-N-(piperidin-4-yl)benzamide

4-((4-(6-methoxypyridin-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-N-((1-acetoxyacetyl)piperidine 4-yl)benzamide

4-((4-(6-methoxypyridin-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-N-((1-acetoxyacetyl)piperidine 4-yl)benzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 15h;100%
Acetol acetate
592-20-1

Acetol acetate

methyl 2,6-di-O-benzyl-3,4-di-O-trimethylsilyl-α-D-galactopyranoside
176757-34-9

methyl 2,6-di-O-benzyl-3,4-di-O-trimethylsilyl-α-D-galactopyranoside

Acetic acid (3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-6-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-ylmethyl ester

Acetic acid (3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-6-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-ylmethyl ester

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate In diethyl ether at -20℃; for 48h;97%
Acetol acetate
592-20-1

Acetol acetate

(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-((R)-1,2-bis-trimethylsilanyloxy-ethyl)-5-methoxy-tetrahydro-furan
176757-35-0

(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-((R)-1,2-bis-trimethylsilanyloxy-ethyl)-5-methoxy-tetrahydro-furan

Acetic acid (R)-4-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-methyl-[1,3]dioxolan-2-ylmethyl ester

Acetic acid (R)-4-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-methyl-[1,3]dioxolan-2-ylmethyl ester

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate In diethyl ether at -20℃; for 48h;96%
Acetol acetate
592-20-1

Acetol acetate

C22H36O8Si2

C22H36O8Si2

C21H26O10

C21H26O10

Conditions
ConditionsYield
Stage #1: Acetol acetate; C22H36O8Si2 In dichloromethane at 20℃; for 1h; Molecular sieve;
Stage #2: With trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate In dichloromethane at -50℃; for 16h;
90%
Acetol acetate
592-20-1

Acetol acetate

(S,S)-2,3-bis(O-trimethylsilyl)-1,4-bisbutane-1,2,3,4-tetrol
158835-58-6

(S,S)-2,3-bis(O-trimethylsilyl)-1,4-bisbutane-1,2,3,4-tetrol

(S,S)-2-(acetoxymethyl)-2-methyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane
171561-22-1

(S,S)-2-(acetoxymethyl)-2-methyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In chloroform Ambient temperature;89%
Acetol acetate
592-20-1

Acetol acetate

Dimethyl phosphite
868-85-9

Dimethyl phosphite

2-(dimethoxyphosphoryl)-2-hydroxypropyl acetate

2-(dimethoxyphosphoryl)-2-hydroxypropyl acetate

Conditions
ConditionsYield
Stage #1: Acetol acetate With tert-butylamine In neat (no solvent) at 20℃; for 0.25h;
Stage #2: With phenylphosphonate In neat (no solvent) at 20℃; for 0.25h;
Stage #3: Dimethyl phosphite In neat (no solvent) at 50℃; for 2h;
89%
Acetol acetate
592-20-1

Acetol acetate

p-Toluic acid
99-94-5

p-Toluic acid

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

benzylamine
100-46-9

benzylamine

2-(benzylamino)-2-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate
1349839-22-0

2-(benzylamino)-2-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 3.25h;88%
Acetol acetate
592-20-1

Acetol acetate

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

m-Toluic acid
99-04-7

m-Toluic acid

2-hydroxy-2-[5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate
1431463-24-9

2-hydroxy-2-[5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;88%
In water at 20℃; for 1h; Green chemistry;85%
3,5-dimethylbenzoic acid
499-06-9

3,5-dimethylbenzoic acid

Acetol acetate
592-20-1

Acetol acetate

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

benzylamine
100-46-9

benzylamine

2-(benzylamino)-2-[5-(3,5-dimethylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate
1349839-21-9

2-(benzylamino)-2-[5-(3,5-dimethylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 3.25h;87%
Acetol acetate
592-20-1

Acetol acetate

p-Toluic acid
99-94-5

p-Toluic acid

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

2-hydroxy-2-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate
1431463-27-2

2-hydroxy-2-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate

Conditions
ConditionsYield
In water at 20℃; for 1h; Green chemistry;86%
In dichloromethane at 20℃; for 1h;83%
(Z)-phenyl hept-4-enoate

(Z)-phenyl hept-4-enoate

Acetol acetate
592-20-1

Acetol acetate

phenyl 4-acetoxy-3-hydroxy-3-methyl-2-[(Z)-pent-2-enyl]butanoate

phenyl 4-acetoxy-3-hydroxy-3-methyl-2-[(Z)-pent-2-enyl]butanoate

Conditions
ConditionsYield
With titanium tetrachloride; triethylamine In dichloromethane at -78℃; for 2h;83%
Acetol acetate
592-20-1

Acetol acetate

anthranilic acid amide
28144-70-9

anthranilic acid amide

2-acetoxymethyl-2-methyl-2,3-dihydroquinazolin-4(1H)-one
1239347-30-8

2-acetoxymethyl-2-methyl-2,3-dihydroquinazolin-4(1H)-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 5h; Reflux;80%
3-bromobenzo[b]thiophene-2-carbaldehyde
10135-00-9

3-bromobenzo[b]thiophene-2-carbaldehyde

Acetol acetate
592-20-1

Acetol acetate

A

C14H13BrO4S

C14H13BrO4S

B

C14H13BrO4S

C14H13BrO4S

C

(R)-4-(3-bromobenzo[b]thiophen-2-yl)-4-hydroxy-2-oxobutyl acetate
1380505-95-2

(R)-4-(3-bromobenzo[b]thiophen-2-yl)-4-hydroxy-2-oxobutyl acetate

Conditions
ConditionsYield
With 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole at 0℃; for 12h; Aldol reaction; optical yield given as %ee; regioselective reaction;A n/a
B n/a
C 80%
benzothiophene-2-carboxaldehyde
3541-37-5

benzothiophene-2-carboxaldehyde

Acetol acetate
592-20-1

Acetol acetate

A

C14H14O4S

C14H14O4S

B

C14H14O4S

C14H14O4S

C

(R)-4-(1-benzothiophen-2-yl)-4-hydroxy-2-oxobutyl acetate
1380505-93-0

(R)-4-(1-benzothiophen-2-yl)-4-hydroxy-2-oxobutyl acetate

Conditions
ConditionsYield
With 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole at 0℃; for 12h; Aldol reaction; optical yield given as %ee; regioselective reaction;A n/a
B n/a
C 78%
3-methylbenzo[b]thiophene-2-carboxaldehyde
22053-74-3

3-methylbenzo[b]thiophene-2-carboxaldehyde

Acetol acetate
592-20-1

Acetol acetate

A

C15H16O4S

C15H16O4S

B

(R)-4-hydroxy-4-(3-methylbenzo[b]thiophen-2-yl)-2-oxobutyl acetate
1380505-94-1

(R)-4-hydroxy-4-(3-methylbenzo[b]thiophen-2-yl)-2-oxobutyl acetate

Conditions
ConditionsYield
With 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole at 0℃; for 12h; Aldol reaction; optical yield given as %ee; regioselective reaction;A n/a
B 78%
Acetol acetate
592-20-1

Acetol acetate

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

dimethyl 2-(1-acetoxypropan-2-ylidene)malonate

dimethyl 2-(1-acetoxypropan-2-ylidene)malonate

Conditions
ConditionsYield
With pyridine; titanium tetrachloride In tetrahydrofuran; dichloromethane at 0 - 20℃; for 3h; Knoevenagel Condensation;74%
Acetol acetate
592-20-1

Acetol acetate

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

Dimethyl phosphite
868-85-9

Dimethyl phosphite

2-((3,4-dimethoxyphenethyl)amino)-2-(dimethoxyphosphoryl)propyl acetate

2-((3,4-dimethoxyphenethyl)amino)-2-(dimethoxyphosphoryl)propyl acetate

Conditions
ConditionsYield
Stage #1: Acetol acetate; 2-(3,4-dimethoxyphenyl)-ethylamine In neat (no solvent) at 20℃; for 0.25h;
Stage #2: With phenylphosphonate In neat (no solvent) at 20℃; for 0.25h;
Stage #3: Dimethyl phosphite In neat (no solvent) at 50℃; for 3h;
73%
Acetol acetate
592-20-1

Acetol acetate

heptanoic acid phenyl ester
56052-14-3

heptanoic acid phenyl ester

phenyl 4-acetoxy-3-hydroxy-3-methylheptanoate

phenyl 4-acetoxy-3-hydroxy-3-methylheptanoate

Conditions
ConditionsYield
With titanium tetrachloride; triethylamine In dichloromethane at -78℃; for 2h;72%
Acetol acetate
592-20-1

Acetol acetate

cis-1,4-anhydroerythritol
4358-64-9

cis-1,4-anhydroerythritol

Acetic acid (3aR,6aS)-2-methyl-tetrahydro-furo[3,4-d][1,3]dioxol-2-ylmethyl ester

Acetic acid (3aR,6aS)-2-methyl-tetrahydro-furo[3,4-d][1,3]dioxol-2-ylmethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;71%
(E)-phenyl hept-4-enoate

(E)-phenyl hept-4-enoate

Acetol acetate
592-20-1

Acetol acetate

phenyl 4-acetoxy-3-hydroxy-3-methyl-2-[(E)-pent-2-enyl]butanoate

phenyl 4-acetoxy-3-hydroxy-3-methyl-2-[(E)-pent-2-enyl]butanoate

Conditions
ConditionsYield
With titanium tetrachloride; triethylamine In dichloromethane at -78℃; for 2h;70%
Acetol acetate
592-20-1

Acetol acetate

Dimethyl phosphite
868-85-9

Dimethyl phosphite

1-amino-2-propene
107-11-9

1-amino-2-propene

2-(allylamino)-2-(dimethoxyphosphoryl)propyl acetate

2-(allylamino)-2-(dimethoxyphosphoryl)propyl acetate

Conditions
ConditionsYield
Stage #1: Acetol acetate; 1-amino-2-propene In neat (no solvent) at 20℃; for 0.25h;
Stage #2: With phenylphosphonate In neat (no solvent) at 20℃; for 0.25h;
Stage #3: Dimethyl phosphite In neat (no solvent) at 50℃; for 2h;
69%
Acetol acetate
592-20-1

Acetol acetate

ethylene glycol
107-21-1

ethylene glycol

methyl (2-methyl-1,3-dioxolan-2-yl)acetate
56446-60-7

methyl (2-methyl-1,3-dioxolan-2-yl)acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene68%
benzothiophene-3-carboxaldehyde
5381-20-4

benzothiophene-3-carboxaldehyde

Acetol acetate
592-20-1

Acetol acetate

A

(R)-4-(benzo[b]thiophen-3-yl)-4-hydroxy-2-oxobutyl acetate
1380505-96-3

(R)-4-(benzo[b]thiophen-3-yl)-4-hydroxy-2-oxobutyl acetate

B

C14H14O4S

C14H14O4S

C

C14H14O4S

C14H14O4S

Conditions
ConditionsYield
With 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole at 0℃; for 12h; Aldol reaction; optical yield given as %ee; regioselective reaction;A 65%
B n/a
C n/a
Hippuric Acid
495-69-2

Hippuric Acid

Acetol acetate
592-20-1

Acetol acetate

A

E-2-phenyl-4(2-acetoxy-1-methylethylidene)-2-oxazoline-5-one
127117-32-2

E-2-phenyl-4(2-acetoxy-1-methylethylidene)-2-oxazoline-5-one

B

Z-2-phenyl-4(2-acetoxy-1-methylethylidene)-2-oxazoline-5-one
127117-33-3

Z-2-phenyl-4(2-acetoxy-1-methylethylidene)-2-oxazoline-5-one

Conditions
ConditionsYield
With lead acetate; acetic anhydride In tetrahydrofuran for 16h; Heating;A 63%
B 1.9%
With lead acetate; acetic anhydride In tetrahydrofuran
Acetol acetate
592-20-1

Acetol acetate

Dimethyl phosphite
868-85-9

Dimethyl phosphite

cyclohexylmethylamine
3218-02-8

cyclohexylmethylamine

2-((cyclohexylmethyl)amino)-2-(dimethoxyphosphoryl)propyl acetate

2-((cyclohexylmethyl)amino)-2-(dimethoxyphosphoryl)propyl acetate

Conditions
ConditionsYield
Stage #1: Acetol acetate; cyclohexylmethylamine In neat (no solvent) at 20℃; for 0.25h;
Stage #2: With phenylphosphonate In neat (no solvent) at 20℃; for 0.25h;
Stage #3: Dimethyl phosphite In neat (no solvent) at 50℃; for 1h;
62%

592-20-1Relevant articles and documents

Investigation of homopolymerization rate of perfluoro-4,5-substituted-2- methylene-1,3-dioxolane derivatives and properties of the polymers

Yang, Yu,Mike?, Franti?ek,Yang, Liang,Liu, Weihong,Koike, Yasuhiro,Okamoto, Yoshiyuki

, p. 277 - 281 (2006)

Five perfluoro-4,5-substituted-2-methylene-1,3-dioxolane monomers were synthesized. These monomers were found to readily polymerized by a free radical initiator in bulk and/or in solutions. Homopolymerization rates were determined using in situ 19F NMR measurements and found to be 0.25 to 1.66 × 10-4 mol L-1 s-1 in 1,1,2-trichlorotrifluoroethane at 41°C using the perfluorodibenzoyl peroxide as an initiator. The rates depend on the substituents on the 4 and 5 positions of the dioxolane. The purified polymers were thermally stable (up to 350°C). They show low refractive indexes (1.33-1.36 at 532 nm). They are transparent from UV to near IR region and have high glass transition temperatures (100-170°C).

AMBER ODORANT

-

Page/Page column 29, (2020/12/11)

The present invention concerns compound of formula (I) in the form of any one of its stereoisomers or as a mixture thereof, and wherein R1 represents a hydrogen atom, a C1-3 alkyl group or C2-3 alkenyl group; X represents an oxygen atom when R2 represents a C1-4 alkyl group or C2-4 alkenyl group or X represents a CH2-O group when R2 represents a C2-4 alkenyl group or a MeC=O group. The use as a perfuming ingredient of the invention's compound and the invention's compound as part of a perfuming composition or of a perfuming consumer product are also part of the present invention.

Exploring the catalytic activity of Lewis-acidic uranyl complexes in the nucleophilic acyl substitution of acid anhydrides

Takao, Koichiro,Akashi, Shin

, p. 12201 - 12207 (2017/03/08)

The catalytic activities of several uranyl complexes, such as N,N′-disalicylidene-o-phenelyenediaminato(ethanol)dioxouranium(vi) (UO2(salophen)EtOH), bis(dibenzoylmethanato)(ethanol)dioxouranium(vi) (UO2(dbm)2EtOH), pentakis(N,N-dimethylformamide)dioxouranium(vi) ([UO2(DMF)5]2+), and tetrakis(triphenylphosphine oxide)dioxouranium(vi) ([UO2(OPPh3)4]2+), were examined in the nucleophilic acyl substitution of acid anhydrides. Among them, [UO2(OPPh3)4]2+ was the most efficient to give ethyl acetate and acetic acid from acetic anhydride (Ac2O) and ethanol, and was resistant towards decomposition during the catalytic reaction. Several nucleophiles were also subjected to the catalytic acylation reaction using acetic and pivalic anhydride. Kinetic and spectroscopic studies suggested that [UO2(OPPh3)4]2+ interacts with Ac2O to form [UO2(Ac2O)(OPPh3)3]2+. Interaction of this actual catalyst with additional Ac2O determines the rate of the overall nucleophilic acyl substitution reaction.

N-Isocyanimino-Triphenylphosphorane (Ph 3Pnnc) as an Efficient Reagent for the Preparation of Fully Substituted 1,3,4-Oxadiazoles via Intramolecular Aza-Wittig Reaction in Water

Jafari, Ali,Ramazani, Ali,Asiabi, Pegah Azimzadeh,Sadri, Fariba,Joo, Sang Woo

, p. 2246 - 2254 (2015/12/20)

An efficient green protocol for the synthesis of 1,3,4-oxadiazoles derivatives via a one-pot three-component reaction of aromatic carboxylic acids, N-isocyanimino-Triphenylphosphorane and ester derivatives of 2-oxopropyl alcohol (2-oxopropyl benzoate, 2-oxopropyl-4-bromobenzoate and 2-oxopropyl acetate) in water at room temperature have been developed. The present methodology offers several advantages such as a simple procedure, high yields, environmental friendliness and the absence of any volatile and hazardous organic solvents.

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