Acetoacetamide supplier | CasNO.5977-14-0

Name
Acetoacetamide
EINECS 227-774-4
CAS No. 5977-14-0
Article Data24
CAS DataBase
Density 1.093 g/cm³
Solubility 1000g/L at 20℃
Melting Point 53-56 °C(lit.)
Formula C₄H₇NO₂
Boiling Point 271 °C at 760 mmHg
Molecular Weight 101.105
Flash Point 80.6 °C
Transport Information
Appearance White to yellowish crystals
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Acetoacetamide(6CI,7CI,8CI);3-Oxobutanamide;3-Oxobutyramide;Acetoacetic acid amide;Acetylacetamide;NSC 632231;a-Acetylacetamide;
PSA 60.16000
LogP 0.15110

Synthetic route

: 141-97-9
ethyl acetoacetate

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
With ammonia In 1,4-dioxane at 30℃; for 24h; Candida antarctica lipase;	59%
With ammonia In 1,4-dioxane at 30℃; for 24h; immobilized lipase from Candida antarctica SP 435A;	59%
With ammonia

: 3-propylamino-2-butenamide

A: 5977-14-0
acetoacetamido

B: 1-propyl-2,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrrole-2,4-dicarboxiamide

Conditions

Conditions	Yield
With oxygen; toluene-4-sulfonic acid In benzene at 60℃; for 24h;	A n/a B 48%

: 15506-53-3
cyclobutane-1,3-dione

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
With ammonia at -15 - -10℃;

: 105-45-3
acetoacetic acid methyl ester

A: 5977-14-0
acetoacetamido

B: 14205-39-1
methyl 3-aminocrotonate

Conditions

Conditions	Yield
With ammonia

: 674-82-8
4-methyleneoxetan-2-one

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
With ammonia In diethyl ether
With ammonium hydroxide for 5h; Yield given;
With ammonia

: 2343-88-6
Acetoacetylfluorid

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
With ammonia In diethyl ether

: 120166-77-0
3-hydroxy 2-buteneamide

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
In water at 25℃; Equilibrium constant;

: (Z)-1-Carbamoyl-propen-2-ol anion

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
With hydrogenchloride In water at 25℃; Rate constant; also in the presence of various buffers;

: 3-hydroxy-2-butenamide

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
With perchloric acid; sodium perchlorate In water at 25℃; Rate constant; also in ethanol/water;

: 75-05-8
acetonitrile

A: 60-35-5
acetamide

B: 5977-14-0
acetoacetamido

C: 63285-19-8
acetamide anion

D: 3-Imino-butyramide

Conditions

Conditions	Yield
With water; hydroxide Mechanism;

...Expand

: 674-82-8
4-methyleneoxetan-2-one

: 74-89-5
methylamine

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
In acetonitrile for 4h; Ambient temperature;

: 141-97-9
ethyl acetoacetate

: ammonium hydroxide

A: 5977-14-0
acetoacetamido

B β-amino-crotonic acid ester: β-amino-crotonic acid ester

...Expand

: 7664-41-7
ammonia

: 7732-18-5
water

: 105-45-3
acetoacetic acid methyl ester

A: 5977-14-0
acetoacetamido

B β-amino-crotonic acid methyl ester: β-amino-crotonic acid methyl ester

...Expand

: 674-82-8
4-methyleneoxetan-2-one

ammonium carbonate: ammonium carbonate

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
With water

: 674-82-8
4-methyleneoxetan-2-one

ammonium hydrogencarbonate: ammonium hydrogencarbonate

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
With water

: 6052-32-0
tetrolic acide amide

: 7732-18-5
water

mercury chloride: mercury chloride

: 5977-14-0
acetoacetamido

...Expand

tetrolic acid amide: tetrolic acid amide

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
With mercury dichloride

: 105-45-3
acetoacetic acid methyl ester

A: 5977-14-0
acetoacetamido

B β-amino-crotonic acid methyl ester: β-amino-crotonic acid methyl ester

Conditions

Conditions	Yield
With ammonium hydroxide

: 3-propylamino-2-butenamide

: 5977-14-0
acetoacetamido

Conditions

Conditions	Yield
With oxygen; toluene-4-sulfonic acid In benzene at 60℃; for 24h;

: 480-96-6
benzofurazan oxide

: 5977-14-0
acetoacetamido

: 23433-66-1
3-methyl-1,4-dioxide-quinoxaline-2-carboxamide

Conditions

Conditions	Yield
Stage #1: benzofurazan oxide; acetoacetamido In isopropyl alcohol at 60℃; for 0.5h; Stage #2: With calcium hydroxide In isopropyl alcohol at 60℃;	100%
With ethanolamine; calcium chloride In methanol at 30℃; for 6h;	76%

: 5977-14-0
acetoacetamido

: 71-43-2
benzene

: 714971-73-0
3,3-diphenyl-butyramide

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid at 25℃; for 6h;	99%

: 5977-14-0
acetoacetamido

: 367965-98-8
methyl cyclohexylaminocarbonyldiazenecarboxylate

: methyl 2-(1-aminocarbonyl-2-hydroxypropen-1-yl)-2-(cyclohexylaminocarbonyl)hydrazinecarboxylate

Conditions

Conditions	Yield
With 2,6-dichloro-benzonitrile In dichloromethane at 20℃; for 1h;	99%

: 5977-14-0
acetoacetamido

: 77771-02-9
3-bromo-4-fluorobenzaldehyde

: 464192-73-2
6-(3-bromo-4-fluorophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-(2H)-pyrimidine

Conditions

Conditions	Yield
With urea	99%

: 5977-14-0
acetoacetamido

: 3623-15-2
phenyl propargyl ketone

: 2-methyl-6-phenylpyridine-3-carboxamide

Conditions

Conditions	Yield
With ammonium acetate In ethanol for 24h; Bohlmann-Rahtz reaction; Heating;	98%
With ammonium acetate In ethanol for 24h; Heating;	98%

: 5977-14-0
acetoacetamido

: 94127-05-6
ethyl 3-[(aminocarbonyl)diazenyl]but-2-enoate

: 94126-63-3
4-Carbamoyl-2,5-dimethyl-1-ureido-1H-pyrrole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With CuCl2*2H2O In tetrahydrofuran for 0.5h; Ambient temperature;	97%

: 5977-14-0
acetoacetamido

: Acetoacetamid-2-sulfonsaeure

Conditions

Conditions	Yield
With chlorosulfonic acid ClSO2OSiMe3 also used;	97%

: 5977-14-0
acetoacetamido

: 65934-19-2
2,4-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 100 - 110℃; for 12h;	97%

: 5977-14-0
acetoacetamido

: 110-62-3
pentanal

: 4-Hexyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile

Conditions

Conditions	Yield
With polyphosphate ester; urea In tetrahydrofuran	97%

: 5977-14-0
acetoacetamido

: 110-62-3
pentanal

: 57-13-6
urea

: 464191-42-2
C10H15N3O

Conditions

Conditions	Yield
With polyphosphate ester In tetrahydrofuran at 75 - 85℃; Biginelli reaction;	97%

...Expand

: 74-96-4
ethyl bromide

aqueous potassium hydroxide: aqueous potassium hydroxide

: 5977-14-0
acetoacetamido

: 98552-44-4
2,2-diethyl-acetoacetic acid amide

Conditions

Conditions	Yield
In methanol; water	96.7%

...Expand

: 5977-14-0
acetoacetamido

: 25769-36-2
1,3,4-triphenyl-1,2-diaza-1,3-butadiene

: 88267-40-7
2-Methyl-4,5-diphenyl-1-phenylamino-1H-pyrrole-3-carboxylic acid amide

Conditions

Conditions	Yield
CuCl2*2H2O In tetrahydrofuran for 11h; Mechanism; Ambient temperature; other arylazoalkenes, other 3-oxoalkanamides;	96%
CuCl2*2H2O In tetrahydrofuran for 11h; Ambient temperature;	96%

: 5977-14-0
acetoacetamido

: 2919-20-2
1,1-di(p-tolyl)ethylene

: 139050-91-2, 139050-92-3
6,6-bis(4-methylphenyl)-4-carbamoyl-3-methyl-1,2-dioxan-3-ol

Conditions

Conditions	Yield
With oxygen; manganese triacetate; acetic acid at 23℃; for 13h;	96%

: 75-15-0
carbon disulfide

: 5977-14-0
acetoacetamido

: 106-93-4
ethylene dibromide

: 836684-88-9
2-(1,3-dithiolan-2-ylidene)-3-oxobutanamide

Conditions

Conditions	Yield
Stage #1: carbon disulfide; acetoacetamido With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: ethylene dibromide In N,N-dimethyl-formamide at 0 - 20℃; for 6h;	95%
Stage #1: carbon disulfide; acetoacetamido With tetrabutylammomium bromide; potassium carbonate In water at 20℃; for 1h; Stage #2: ethylene dibromide In water at 20℃; for 8h; Stage #3: With sulfuric acid In dichloromethane at 0 - 20℃; for 10h;

...Expand

: 5977-14-0
acetoacetamido

: 94-41-7
benzalacetophenone

A: 61448-56-4
2-methyl-4,6-diphenylpyridine-3-carboxamide

B: 57839-64-2
2-oxo-4,6-diphenylcyclohex-3-enecarboxamide

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate; ammonium acetate In ethanol for 15h; Reagent/catalyst; Reflux;	A 95% B 5%

...Expand

: 5977-14-0
acetoacetamido

: 4224-96-8
3-phenyl-1-p-tolylprop-2-en-1-one

: 2-methyl-6-(4-methylphenyl)-4-phenylpyridine-3-carboxamide

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate; ammonium acetate In ethanol for 15h; Reflux;	95%

: 5977-14-0
acetoacetamido

: 21551-47-3
4,4'-Dimethylchalcon

: 1398101-54-6
4,6-bis(4-methylphenyl)-2-methylnicotinamide

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate; ammonium acetate In ethanol for 15h; Reflux;	95%

: 5977-14-0
acetoacetamido

: 959-33-1
3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one

: 4-(4-methoxyphenyl)-2-methyl-6-phenylpyridine-3-carboxamide

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate; ammonium acetate In ethanol for 15h; Reflux;	95%

: 5977-14-0
acetoacetamido

: 20725-25-1, 22966-30-9, 19672-59-4
1,3-bis(4-chlorophenyl)prop-2-en-1-one

: 1398101-56-8
4,6-bis(4-chlorophenyl)-2-methylnicotinamide

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate; ammonium acetate In ethanol for 24h; Reflux;	95%

: 21962-45-8
4-formyl-3-methoxy-benzonitrile

: 5977-14-0
acetoacetamido

: (2E/2Z)-2-(4-cyano-2-methoxybenzylidene)-3-oxobutanamide

Conditions

Conditions	Yield
With piperidine; acetic acid In dichloromethane for 4h; Reflux;	95%
With piperidine; acetic acid In dichloromethane Reflux;	77.7%

: 5977-14-0
acetoacetamido

: 63160-41-8
1-aminocarbonyl-3-methyl-4-methoxycarbonyl-1,2-diaza-1,3-diene

: 94126-57-5
4-Carbamoyl-2,5-dimethyl-1-ureido-1H-pyrrole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
CuCl2*2H2O In tetrahydrofuran for 0.5h; Ambient temperature;	94%

: 5977-14-0
acetoacetamido

: 99-61-6
3-nitro-benzaldehyde

: 57-13-6
urea

: 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile

Conditions

Conditions	Yield
With polyphosphate ester In tetrahydrofuran at 75 - 85℃; for 3.75h; Biginelli reaction;	94%

...Expand

: 4651-72-3
2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene

: 5977-14-0
acetoacetamido

: 960617-85-0
2-methyl-4-phenyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine-3-carboxamide

Conditions

Conditions	Yield
With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; for 10h; Friedlaender rection;	93%

: 5977-14-0
acetoacetamido

: 6046-93-1
copper(II) acetate monohydrate

: bis(1-N-amino-1,3-butanedionate)copper(II)

Conditions

Conditions	Yield
In ethanol; water copper acetate in H2O added dropwise to the β-ketoamide in EtOH, under stirring; reaction time: 30 min; evapd. at ca. 40°C, repeated treating with water/EtOH 1/1 and concn.; solid filtered off, dried under vacuum, washed with ethylacetate, elem. anal.;	93%

: 5977-14-0
acetoacetamido

: 106-96-7
propargyl bromide

: 99060-20-5
2-acetyl-2-(prop-2-ynyl)pent-4-ynamide

Conditions

Conditions	Yield
Stage #1: acetoacetamido With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 4h;	93%

: 5977-14-0
acetoacetamido

: 2809-67-8
oct-2-yne

: 2-acetyl-3-vinyloctanamide

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; trifluoroacetic acid; bis[2-(diphenylphosphino)phenyl] ether In ethanol; 1,2-dichloro-ethane at 80℃; for 16h; Inert atmosphere; Sealed tube; Schlenk technique; diastereoselective reaction;	93%

: 5977-14-0
acetoacetamido

: 4996-22-9
4-nitrophenylglyoxal

: 3-methyl-6-(4-nitrophenyl)pyridazine-4-carboxamide

Conditions

Conditions	Yield
With hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene In water at 25℃; for 0.25h; Green chemistry; regioselective reaction;	93%

: 5977-14-0
acetoacetamido

: 367965-97-7
methyl (2-chloroethylamino)carbonyldiazenecarboxylate

: methyl 2-(1-aminocarbonyl-2-hydroxypropen-1-yl)-2-(2-chloroethylaminocarbonyl)hydrazinecarboxylate

Conditions

Conditions	Yield
With 2,6-dichloro-benzonitrile In ethyl acetate at 20℃; for 1h;	92%

: 5977-14-0
acetoacetamido

: 94-41-7
benzalacetophenone

: 61448-56-4
2-methyl-4,6-diphenylpyridine-3-carboxamide

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate; ammonium acetate In ethanol for 15h; Reflux;	92%

: 88-21-1
2-amino-1-benzenesulfonic acid

: 5977-14-0
acetoacetamido

: sodium (Z)-2-(2-(1-amino-1,3-dioxobutan-2-ylidene)hydrazineyl)benzenesulfonate

Conditions

Conditions	Yield
Stage #1: 2-amino-1-benzenesulfonic acid With sodium hydroxide; sodium nitrite In water at 0 - 5℃; for 0.0833333h; Stage #2: With hydrogenchloride In water at 0 - 5℃; for 0.5h; Stage #3: acetoacetamido With sodium acetate; sodium hydroxide In ethanol; water for 1h;	92%

Acetoacetamide Chemical Properties

Product Name: Acetoacetamide (CAS NO.5977-14-0)

Molecular Formula: C₄H₇NO₂
Molecular Weight: 101.1g/mol
Mol File: 5977-14-0.mol
EINECS: 227-774-4
Melting Point: 53-56 °C(lit.)
Boiling point: 271 °C at 760 mmHg
Flash Point: 80.6 °C
Density: 1.093 g/cm³
Surface Tension: 38.5 dyne/cm
Enthalpy of Vaporization: 50.93 kJ/mol
Vapour Pressure: 0.0066 mmHg at 25°C
XLogP3-AA: -1
H-Bond Donor: 1
H-Bond Acceptor: 2
Structure Descriptors of Acetoacetamide (CAS NO.5977-14-0):
IUPAC Name: 3-oxobutanamide
Canonical SMILES: CC(=O)CC(=O)N
InChI: InChI=1S/C4H7NO2/c1-3(6)2-4(5)7/h2H2,1H3,(H2,5,7)
InChIKey: GCPWJFKTWGFEHH-UHFFFAOYSA-N
Product Categories: Pharmaceutical Intermediates; Amides; Carbonyl Compounds; Organic Building Blocks

Acetoacetamide Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD	oral	> 500mg/kg (500mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS	National Technical Information Service. Vol. OTS0544866,

Acetoacetamide Safety Profile

Safety Information of Acetoacetamide (CAS NO.5977-14-0):
WGK Germany: 1
RTECS: EJ3667188

Acetoacetamide Specification

Acetoacetamide , its CAS NO. is 5977-14-0, the synonyms are 3-Oxobutanamide ; Acetoacetic acid amide ; NSC 632231 ; Butanamide, 3-oxo- .

Product Name

Acetoacetamide

Synthetic route

Acetoacetamide Chemical Properties

Acetoacetamide Toxicity Data With Reference

Acetoacetamide Safety Profile

Acetoacetamide Specification

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