2044-64-6

Basic information

• Product Name: N,N-Dimethylacetoacetamide
• Synonyms: Acetoacetamide, N,N-dimethyl-;Acetylacetamide, N,N-dimethyl-;Butanamide, N,N-dimethyl-3-oxo-;Butanamide,N,N-dimethyl-3-oxo-;Dimethylamid kyseliny acetoctove;dimethylamidkyselinyacetoctove;Acetoacetdimethylamide;N,N-Dimethylacetoacetamide (approx. 80% in water)
• CAS NO: 2044-64-6
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• EINECS: 218-059-8
• Mol File: 2044-64-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: -55 °C
• Boiling Point: 105 °C(lit.)
• Flash Point: 252 °F
• Appearance: APHA: ≤350/
• Density: 1.067 g/mL at 25 °C
• Vapor Pressure: 0.018mmHg at 25°C
• Refractive Index: n20/D 1.447
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: H2O: soluble
• PKA: 12.82±0.46(Predicted)
• Water Solubility: hydrolysis SLOWLY
• BRN: 1755038
• CAS DataBase Reference: N,N-Dimethylacetoacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethylacetoacetamide(2044-64-6)
• EPA Substance Registry System: N,N-Dimethylacetoacetamide(2044-64-6)

Safety Data

• Hazard Codes: N
• Statements: 36/37/38-51/53
• Safety Statements: 26-36-61
• RIDADR: UN 3082 9 / PGIII
• RTECS: AK4035000
• Hazardous Substances Data: 2044-64-6(Hazardous Substances Data)

Usage

Description

N,N-dimethylacetoacetamide is a clear, colorless to yellow liquid used as a general purpose, low color generating co-promoter for many unsaturated polyester (FRP) resin formulations. It is also used in the production of low VOC unsaturated polyester (FRP) systems for coatings and as an intermediate for the production of insecticides.

Application

N,N-Dimethylacetylacetamide is an organic intermediate that can be used to prepare thioamide compounds. As an important thiocarboxylic acid derivative, thioamide compounds have received extensive attention in pharmaceutical synthesis, chemical engineering and related fields. Thioamide and its derivatives have a wide range of applications in analysis, materials, and electrochemistry. They are not only used in the production of polymerization inhibitors, catalysts, stabilizers, pesticides, etc., but also in the production of pharmaceutical raw materials, vulcanizing agents, and chemicals. Coupling reagents, collectors, etc.

Chemical Properties

Clear, colorless to yellow liquid

Uses

Different sources of media describe the Uses of 2044-64-6 differently. You can refer to the following data:
1. N,N-Dimethylacetamide is used as intermediate for the production of insecticides, e.g. dicrotophos and as a promoter in unsaturated polyester resins. Product Data Sheet
2. N,N-Dimethylacetoacetamide can be used as promoter for unsaturated polyester resins.
3. N,N-Dimethyl-3-oxobutanamide is used as a reactant in the asymmetric hydrogenation of functionalized ketones in presence of chiral bis(diphenylphosphino)binaphthyl ruthenium complex.

General Description

The product is an 80% solution of N,N-dimethylacetoacetamide (DMAA) in water.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C6H11NO2/c1-4(8)6(2,3)5(7)9/h1-3H3,(H2,7,9)

Synthetic route

15-Hydroxy-pentadecanoic acid (Z)-2-dimethylcarbamoyl-1-methyl-vinyl ester (89611-22-3) → pentadecanolide (106-02-5) + N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
With magnesium bromide In tetrahydrofuran at 55℃; other solvents, temperatures and reagent;	A 90% B n/a

13-Hydroxy-tridecanoic acid (Z)-2-dimethylcarbamoyl-1-methyl-vinyl ester (89611-21-2) → N,N-Dimethylacetoacetamid (2044-64-6) + oxacyclotetradecan-2-one (1725-04-8)

Conditions	Yield
With (1S)-10-camphorsulfonic acid In toluene at 80℃; for 10h; other solvent and temperature;	A n/a B 83%

2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) + dimethyl amine (124-40-3) → N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
In toluene at 20℃; for 12.25h; Reflux;	83%
In water; toluene at 160℃; for 0.166667h; Microwave irradiation; Inert atmosphere;	73%
In tetrahydrofuran; toluene at 160℃; for 0.166667h; Microwave irradiation;
In 5,5-dimethyl-1,3-cyclohexadiene Reflux;

(E)-(R)-12-Hydroxy-octadec-9-enoic acid (Z)-2-dimethylcarbamoyl-1-methyl-vinyl ester (65545-12-2) → (-)-(R,E)-12-hydroxy-9-octadecenoic acid lactone (59744-10-4) + N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
With (1S)-10-camphorsulfonic acid In toluene at 80℃; other solvent and temperature;	A 82% B n/a

(E)-4-[(1R,2S,4R)-2-((E)-(S)-6-Hydroxy-hept-1-enyl)-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-4-(2-methoxy-ethoxymethoxy)-but-2-enoic acid (Z)-2-dimethylcarbamoyl-1-methyl-vinyl ester (88526-22-1, 88588-18-5) → N,N-Dimethylacetoacetamid (2044-64-6) + 7-epi-Brefeldine A (60043-55-2, 62989-95-1, 88587-09-1, 88588-19-6)

Conditions	Yield
With (1S)-10-camphorsulfonic acid In toluene at 80℃;	A n/a B 74%

N,N-dimethylammonium chloride (506-59-2) + ethyl acetoacetate (141-97-9) → N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
With dmap In toluene Reflux;	70%

N,N-dimethyl acetamide (127-19-5) → N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
With n-butyl magnesium bromide In tetrahydrofuran for 1.5h; Ambient temperature;	54%
With trichlorophosphate; benzene
With trichlorophosphate In benzene
With nitromesitylene; p-MeOPhN(MgBr)2 In tetrahydrofuran at 0℃; for 1h; Yield given;

N,N-dimethyl acetamide (127-19-5) + N-Butyl-N-((E)-propenyl)-propionamide (92444-87-6) → N,N-Dimethylacetoacetamid (2044-64-6) + 1-benzyl-4,5-dimethyl-2-pyridone

Conditions	Yield
With trichlorophosphate	A 24% B 18%

4-methyleneoxetan-2-one (674-82-8) + diethyl ether (60-29-7) + dimethyl amine (124-40-3) → N,N-Dimethylacetoacetamid (2044-64-6)

4-methyleneoxetan-2-one (674-82-8) + dimethyl amine (124-40-3) → N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
With diethyl ether
In diethyl ether
In toluene at 70℃; for 3h;

Ketene (463-51-4) + Tetramethylborazen (1113-30-0) → N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
(i) THF, (ii) aq. MeOH; Multistep reaction;

β-(Trimethylsilyloxy)vinylessigsaeure-N-dimethylamid (14857-15-9) → N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
With methanol

4-(dimethylamino)but-3-yn-2-one (20568-22-3) → N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
With water
Multi-step reaction with 2 steps 1: 95 percent / tetrahydrofuran / 0 °C 2: 10-Camphersulfonsaeure / toluene / 10 h / 80 °C / other solvent and temperature View Scheme
Multi-step reaction with 2 steps 1: 95 percent / tetrahydrofuran / 0 °C 2: MgBr2- Et2O / tetrahydrofuran / 55 °C / other solvents, temperatures and reagent View Scheme
Multi-step reaction with 2 steps 1: 95 percent / tetrahydrofuran / 0 °C 2: 10-Camphersulfonsaeure / toluene / 80 °C / other solvent and temperature View Scheme
Multi-step reaction with 2 steps 1: 97 percent / tetrahydrofuran / 0 °C 2: 10-Camphersulfonsaeure / toluene / 80 °C View Scheme

ethyl acetoacetate (141-97-9) + dimethylamino tributyltin (1067-24-9) → N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
In diethyl ether

N,N-dimethyl acetamide (127-19-5) + benzene (71-43-2) + phosphorus yl chloride → N,N-Dimethylacetoacetamid (2044-64-6)

(E)-4-(dimethylamino)but-3-en-2-one (2802-08-6) → N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) Br2, (ii) Et3N 2: KOtBu 3: H2O View Scheme

1-dimethylamino-2-bromo-1-buten-3-one (26387-68-8) → N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOtBu 2: H2O View Scheme

dimethylchloroamine (1585-74-6) + ethyl acetoacetate (141-97-9) → N,N-Dimethylacetoacetamid (2044-64-6)

Conditions	Yield
With dmap In toluene Reflux;

N,N-Dimethylacetoacetamid (2044-64-6) → 2-diazo-3-oxobutyric acid N,N-dimethyl amide

Conditions	Yield
With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile at 20℃; for 16h; Inert atmosphere;	100%
With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile at 20℃; for 16h; Inert atmosphere;	100%
With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile at 20℃; for 16h; Regitz Diazo Transfer; Inert atmosphere;	100%

N,N-Dimethylacetoacetamid (2044-64-6) + rac-1-(4-methoxyphenyl)-ethanol (3319-15-1) → 2-[1-(4-methoxyphenyl)-ethyl]-N,N-dimethyl-3-oxobutyramide

Conditions	Yield
With hafnium(IV) trifluoromethanesulfonate In nitromethane at 60℃; for 12h;	98%

N,N-Dimethylacetoacetamid (2044-64-6) → 2-fluoro-N,N-dimethyl-3-oxobutanamide

Conditions	Yield
With Selectfluor In PEG-400 at 60℃; for 11h;	98%
With iodosyl-o-toluene; triethylamine hydrofluoride In dichloromethane; water at 40℃; for 2h; Reagent/catalyst;	91%
With Selectfluor In water; acetonitrile at 20℃; for 4h; Schlenk technique; Sealed tube; chemoselective reaction;	82%

1,1-Diphenylmethanol (91-01-0) + N,N-Dimethylacetoacetamid (2044-64-6) → C19H21NO2 (1360433-83-5)

Conditions	Yield
With silica gel supported sodium hydrogen sulfate In 1,1-dichloroethane at 80℃; for 3h;	97%

N,N-Dimethylacetoacetamid (2044-64-6) + tert-butyl 2-(3-methoxyprop-1-ynyl)phenylcarbamate (1262034-08-1) → C20H26N2O4

Conditions	Yield
Stage #1: N,N-Dimethylacetoacetamid; tert-butyl 2-(3-methoxyprop-1-ynyl)phenylcarbamate With magnesium chloride In 1,4-dioxane at 23℃; for 0.25h; Inert atmosphere; Stage #2: With Zeise's dimer In 1,4-dioxane at 70℃; for 72h; Inert atmosphere;	97%

benzofurazan oxide (480-96-6) + N,N-Dimethylacetoacetamid (2044-64-6) → 3-methyl-1,4-dioxy-quinoxaline-2-carboxylic acid dimethylamide (23696-31-3)

Conditions	Yield
With ethanolamine; calcium chloride In methanol at 30℃; for 8h;	96%

N,N-Dimethylacetoacetamid (2044-64-6) + tert-butyl benzylidenecarbamate (177896-09-2) → C20H24N2O2

Conditions	Yield
1,3-diTs-2,3-dihydro-2-oxo-benzo[1,3,2]-diaza-phosphole-2-ol In chloroform-d1 at 20℃; for 0.166667h; Product distribution / selectivity;	96%
2,6-bis-(4-naphthalen-2-yl-phenyl)-4-oxo-3,5-dioxa-4λ5-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-ol In chloroform-d1 at 20℃; Product distribution / selectivity;

4-Fluorothiophenol (371-42-6) + N,N-Dimethylacetoacetamid (2044-64-6) → 2-((4-fluorophenyl)thio)-N,N-dimethylacetamide

Conditions	Yield
With oxygen; sodium hydroxide In acetonitrile at 22 - 25℃; for 18h;	96%

cyclopent-2-enone (930-30-3) + N,N-Dimethylacetoacetamid (2044-64-6) → N,N-dimethyl-3-oxo-2-(3-oxocyclopentyl)butanamide

Conditions	Yield
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 25℃; for 6h; Michael reaction;	95%

N,N-Dimethylacetoacetamid (2044-64-6) + thiophenol (108-98-5) → α-(phenylthio)-N,N-dimethylacetamide (78698-19-8)

Conditions	Yield
With oxygen; sodium hydroxide In acetonitrile at 22 - 25℃; for 18h; Reagent/catalyst; Solvent; Temperature;	95%

N,N-Dimethylacetoacetamid (2044-64-6) + (E)-N-benzylidenebenzylamine (27845-50-7) → C20H24N2O2

Conditions	Yield
1,3-diTs-2,3-dihydro-2-oxo-benzo[1,3,2]-diaza-phosphole-2-ol In chloroform-d1 at 20℃; for 0.166667h; Product distribution / selectivity;	94%

N,N-Dimethylacetoacetamid (2044-64-6) + toluene-4-sulfonic acid (104-15-4) → 1-(dimethylamino)-1,3-dioxobutan-2-yl 4-methylbenzenesulfonate (1242025-16-6)

Conditions	Yield
With 4-(difluoroiodo)toluene In dichloromethane at 20℃; for 0.0833333h;	94%

N,N-Dimethylacetoacetamid (2044-64-6) + para-thiocresol (106-45-6) → 1-(p-tolylthio)-N,N-dimethylacetamide (94404-19-0)

Conditions	Yield
With oxygen; sodium hydroxide In acetonitrile at 22 - 25℃; for 18h;	94%

N,N-Dimethylacetoacetamid (2044-64-6) + p-Chlorothiophenol (106-54-7) → 2-((4-chlorophenyl)thio)-N,N-dimethylacetamide

Conditions	Yield
With oxygen; sodium hydroxide In acetonitrile at 22 - 25℃; for 18h;	94%

N,N-Dimethylacetoacetamid (2044-64-6) + Benzeneselenol (645-96-5) → N,N-dimethyl-2-(phenylselanyl)acetamide (819069-93-7)

Conditions	Yield
With oxygen; sodium hydroxide In acetonitrile at 22 - 25℃; for 18h;	94%

N,N-Dimethylacetoacetamid (2044-64-6) + N-butylamine (109-73-9) → 3-butylamino-N,N-dimethyl-(Z)-2-butenamide (827574-12-9)

Conditions	Yield
With 4 A molecular sieve In hexane at 50℃; for 6h;	93%

N,N-Dimethylacetoacetamid (2044-64-6) + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (E)-2-acetyl-N,N-dimethyl-5-phenylpent-4-enamide

Conditions	Yield
With pyrrolidine; dichloro( 1,5-cyclooctadiene)platinum(ll); acetic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 60℃; for 5h; Inert atmosphere; Schlenk technique; Microwave irradiation; regioselective reaction;	93%

N,N-Dimethylacetoacetamid (2044-64-6) + 4-t-butylbenzenethiol (2396-68-1) → 2-((4-(tert-butyl)phenyl)thio)-N,N-dimethylacetamide

Conditions	Yield
With oxygen; sodium hydroxide In acetonitrile at 22 - 25℃; for 18h;	92%

N,N-Dimethylacetoacetamid (2044-64-6) + 3-(2-nitroethenyl)-1H-indole (3156-51-2) → 2-acetyl-3-(1H-indol-3-yl)-N,N-dimethyl-4-nitrobutanamide (1370438-11-1)

Conditions	Yield
With potassium carbonate at 20℃; for 0.75h; Michael type addition; Sonication; Neat (no solvent);	91%

N,N-Dimethylacetoacetamid (2044-64-6) → (S)-3-hydroxy-N,N-dimethylbutanamide (89209-12-1)

Conditions	Yield
With [Ir(H)2((R)-N-((1,3-dithian-2-yl)methyl)-7'-(bis(3,5-di-tert-butylphenyl)phosphanyl)-1,1'-spirobiindanyl-7-amine)Cl]; hydrogen; sodium hydroxide In methanol at 25 - 30℃; under 7600.51 Torr; for 0.5h; Autoclave; enantioselective reaction;	91%

methanol (67-56-1) + N,N-Dimethylacetoacetamid (2044-64-6) → 2-methoxy-N,N-dimethyl-3-oxobutanamide (1242025-66-6)

Conditions	Yield
With 4-(difluoroiodo)toluene at 20℃; for 1h;	90%

N,N-Dimethylacetoacetamid (2044-64-6) + para-bromobenzenethiol (106-53-6) → 2-((4-bromophenyl)thio)-N,N-dimethylacetamide

Conditions	Yield
With oxygen; sodium hydroxide In acetonitrile at 22 - 25℃; for 18h;	90%

N,N-Dimethylacetoacetamid (2044-64-6) + 3-Bromothiophenol (6320-01-0) → 2-((3-bromophenyl)thio)-N,N-dimethylacetamide

Conditions	Yield
With oxygen; sodium hydroxide In acetonitrile at 22 - 25℃; for 18h;	90%

N,N-Dimethylacetoacetamid (2044-64-6) + 1,1-bis(p-chlorophenyl)ethene (2642-81-1) → 6,6-bis(4-chlorophenyl)-4-(dimethylcarbamoyl)-3-methyl-1,2-dioxan-3-ol (139050-99-0, 139051-00-6)

Conditions	Yield
With oxygen; manganese triacetate; acetic acid at 23℃; for 12h;	89%

N,N-Dimethylacetoacetamid (2044-64-6) → 2-diazo-N,N-dimethyl-acetamide (62285-47-6)

Conditions	Yield
Stage #1: N,N-Dimethylacetoacetamid With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile for 0.75h; Inert atmosphere; Stage #2: With potassium hydroxide In water; acetonitrile for 3h; Inert atmosphere;	89%
With 4-toluenesulfonyl azide; triethylamine In acetonitrile at 21℃; for 24h;	50%
Stage #1: N,N-Dimethylacetoacetamid With 4-toluenesulfonyl azide; triethylamine In acetonitrile at 20℃; for 10h; Cooling with ice; Stage #2: With potassium hydroxide In diethyl ether; water at 20℃; for 1h;

4-Methoxybenzenethiol (696-63-9) + N,N-Dimethylacetoacetamid (2044-64-6) → 2-((4-methoxyphenyl)thio)-N,N-dimethylacetamide

Conditions	Yield
With oxygen; sodium hydroxide In acetonitrile at 22 - 25℃; for 18h;	89%

Thiophene-2-thiol (7774-74-5) + N,N-Dimethylacetoacetamid (2044-64-6) → N,N-dimethyl-2-(thiophen-2-ylthio)acetamide

Conditions	Yield
With oxygen; sodium hydroxide In acetonitrile at 22 - 25℃; for 18h;	89%

N,N-Dimethylacetoacetamid (2044-64-6) + di(p-tolyl) disulfide (103-19-5) → 1-(p-tolylthio)-N,N-dimethylacetamide (94404-19-0)

Conditions	Yield
With oxygen; copper(II) acetate monohydrate; caesium carbonate In acetonitrile at 130℃; for 16h; Sealed tube;	88%

N,N-Dimethylacetoacetamid (2044-64-6) + 2-(hydroxy(phenyl)methyl)phenol (40473-50-5) → N,N-dimethyl-2-methyl-4-phenyl-4H-chromene-3-amide (1632130-98-3)

Conditions	Yield
With sodium bisulfate supported on silica gel In 1,2-dichloro-ethane at 80℃; for 5h;	88%

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 60-29-7 diethyl ether 
• 124-40-3 dimethyl amine 
• 20568-22-3 4-(dimethylamino)but-3-yn-2-one 
• 127-19-5 N,N-dimethyl acetamide 
• 92444-87-6 N-Butyl-N-((E)-propenyl)-propionamide 
• 65545-12-2 (E)-(R)-12-Hydroxy-octadec-9-enoic acid (Z)-2-dimethylcarbamoyl-1-methyl-vinyl ester 
• 71-43-2 benzene 
• 506-59-2 N,N-dimethylammonium chloride 
• 141-97-9 ethyl acetoacetate 
• 1585-74-6 dimethylchloroamine 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 26387-68-8 1-dimethylamino-2-bromo-1-buten-3-one 
• 2802-08-6 (E)-4-(dimethylamino)but-3-en-2-one 

Downstream Products

• 5810-11-7 2-chloro-N,N-dimethylacetoacetamide 
• 70155-30-5 3,5,7-Trioxo-7-phenyl-heptanoic acid dimethylamide 
• 43015-36-7 2-[(Z)-Hydroxyimino]-N,N-dimethyl-3-oxo-butyramide 
• 70155-25-8 3-Oxo-5-phenyl-pentanoic acid dimethylamide 
• 83305-62-8 2-benzyl-N,N-dimethyl-3-oxobutanamide 
• 127-19-5 N,N-dimethyl acetamide 
• 83305-52-6 N,N-dimethyl-α-(3-chloro-2-butenyl)acetoacetamide 
• 36764-06-4 N,N,3-trimethyl-4-oxopentanamide 
• 419567-10-5 3-oxo-2-phenylselanyl-hept-6-enoic acid dimethylamide 
• 419567-11-6 8-methyl-3-oxo-2-phenylselanyl-non-7-enoic acid dimethylamide 
• 419567-12-7 (Z)-3-Oxo-2-phenylselanyl-dec-7-enoic acid dimethylamide 
• 419567-13-8 7-methyl-3-oxo-2-phenylselanyl-oct-7-enoic acid dimethylamide 
• 419567-17-2 6-methyl-2-oxo-6-phenylselanyl-cycloheptanecarboxylic acid dimethylamide 
• 419567-20-7 (E)-6-Methyl-3-oxo-2-phenylselanyl-undeca-6,10-dienoic acid dimethylamide 

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