110-20-3

Basic information

• Product Name: ACETONE SEMICARBAZONE
• Synonyms: 2-(1-methylethylidene)-hydrazinecarboxamid;Hydrazinecarboxamide, 2-(1-methylethylidene)-;AURORA KA-350;ACETONE SEMICARBAZONE;2-Propanone semicarbazone ;Acetonesemicarbazone;2-Propanonesemicarbazone ;Acetone semicarbazon;Acetone Semecarbazone
• CAS NO: 110-20-3
• Molecular Formula: C₄H₉N₃O
• Molecular Weight: 115.13
• EINECS: 203-746-7
• Product Categories: Pharmaceutical Intermediates;API
• Mol File: 110-20-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 189-190°C
• Boiling Point: 215.41°C (rough estimate)
• Appearance: Clear liquid
• Density: 1.1906 (rough estimate)
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 12.31±0.46(Predicted)
• Merck: 14,8444
• BRN: 970110
• CAS DataBase Reference: ACETONE SEMICARBAZONE(CAS DataBase Reference)
• NIST Chemistry Reference: ACETONE SEMICARBAZONE(110-20-3)
• EPA Substance Registry System: ACETONE SEMICARBAZONE(110-20-3)

Safety Data

• Statements: 22
• Safety Statements: 22-36/37-36
• RTECS: AL7175000
• TSCA: Yes
• Hazardous Substances Data: 110-20-3(Hazardous Substances Data)

Usage

Uses

Acetone Semicarbazone is used as the starting material to synthesize Isazophos which is a pesticide.

Safety Profile

Poison by intravenous route. Whenheated to decomposition it emits toxic fumes of NOx.

Purification Methods

Acetone semicarbazone crystallises from water or from aqueous EtOH. [Beilstein 3 H 101, 3 I 48, 3 II 81, 3 III 189, 3 IV 179.]

InChI:InChI=1/C4H9N3O/c1-3(2)6-7-4(5)8/h1-2H3,(H3,5,7,8)

Synthetic route

semicarbazide hydrochloride (563-41-7) + acetone (67-64-1) → acetone semicarbazone (110-20-3)

Conditions	Yield
With sodium acetate In water	75%
With sodium acetate In water at 20℃; for 18h;	75%
With sodium acetate In ethanol; water for 0.5h;
With sodium acetate In water at 20℃;

isopropyl-diazenecarboxylic acid amide → acetone semicarbazone (110-20-3)

Conditions	Yield
an der Luft;

hydrazine carboxamide (4426-72-6, 51433-48-8) + acetone (67-64-1) → acetone semicarbazone (110-20-3)

Conditions	Yield
With acetic acid
With alkali

4-isopropylidene-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one (22123-17-7) + hydrazine carboxamide (4426-72-6, 51433-48-8) → edaravone (89-25-8) + acetone semicarbazone (110-20-3)

Conditions	Yield
With sodium acetate In ethanol for 1h; Product distribution; Ambient temperature;

5-Methyl-4-(1-methylethylidene)-2-(4'-chlorophenyl)-2,4-dihydro-3H-pyrazol-3-one (108161-18-8) + hydrazine carboxamide (4426-72-6, 51433-48-8) → 1-(4-chlorophenyl)-3-methyl-2-pyrazolin-5-one (13024-90-3) + acetone semicarbazone (110-20-3)

Conditions	Yield
With sodium acetate In ethanol for 1h; Product distribution; Ambient temperature;

5-Methyl-4-(1-methylethylidene)-2-(4'-methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-one (85921-22-8) + hydrazine carboxamide (4426-72-6, 51433-48-8) → 1-(4-methoxyphenyl)-3-methyl-2-pyrazolin-5-one (60798-06-3) + acetone semicarbazone (110-20-3)

Conditions	Yield
With sodium acetate In ethanol for 1h; Product distribution; Ambient temperature;

5-Methyl-4-(1-methylethylidene)-2-(4'-nitrophenyl)-2,4-dihydro-3H-pyrazol-3-one (76973-30-3) + hydrazine carboxamide (4426-72-6, 51433-48-8) → 1-(4'-nitrophenyl)-3-methyl-5-pyrazolone (6402-09-1) + acetone semicarbazone (110-20-3)

Conditions	Yield
With sodium acetate In ethanol for 1h; Product distribution; Ambient temperature;

water (7732-18-5) + semicarbazide hydrochloride (563-41-7) + potassium acetate (127-08-2) + propan-2-one azine (627-70-3) → acetone semicarbazone (110-20-3)

hydrazine carboxamide (4426-72-6, 51433-48-8) + acetone sodium bisulfite → acetone semicarbazone (110-20-3)

Conditions	Yield
With water
With ethanol
With benzene

1-isopropyl semicarbazide (14869-57-9) + dihydrogen peroxide (7722-84-1) → acetone semicarbazone (110-20-3)

isopropyl-diazenecarboxylic acid amide + acid → acetone semicarbazone (110-20-3)

isopropyl-diazenecarboxylic acid amide + water (7732-18-5) + KOH-solution → acetone semicarbazone (110-20-3)

1-isopropyl semicarbazide (14869-57-9) + water (7732-18-5) + permanganate → acetone semicarbazone (110-20-3)

1-isopropyl semicarbazide (14869-57-9) + sulfuric acid (7664-93-9) + permanganate → isopropyl-diazenecarboxylic acid amide + acetone semicarbazone (110-20-3)

methanolic sodium methylate + methyl chloroacetate (96-34-4) + acetone semicarbazone (110-20-3) + 1-methyl-3-(5-nitro-furan-2-yl)-1H-pyrazole-4-carbaldehyde (61619-60-1) → 1-[1-methyl-3-(5-nitro-furan-2-yl)-1H-pyrazol-4-ylmethyleneamino]-imidazolidine-2,4-dione (61620-57-3)

Conditions	Yield
With hydrogenchloride In N-methyl-acetamide; water; isopropyl alcohol	90%

bis(cyclopentadienyl)titanium dichloride (1271-19-8) + acetone semicarbazone (110-20-3) → (C5H5)2Ti((CH3)2CNNCONH2)Cl

Conditions	Yield
With triethylamine In tetrahydrofuran byproducts: triethylamine hydrochloride; stirring for 25hours, filtration, evaporation; recryst., elem. anal.;	90%

ethanolamine (141-43-5) + acetone semicarbazone (110-20-3) → acetone 4-(2-hydroxyethyl)semicarbazone (98278-63-8)

Conditions	Yield
In toluene Heating;	81%
In toluene for 7h; transamination; Heating;	81%

2-isopropoxy-1,3,2-benzodioxaborole (61676-63-9) + acetone semicarbazone (110-20-3) → C6H4(O)2B(CH3)2CNNCONH2 (90963-54-5)

Conditions	Yield
In benzene byproducts: isopropanol; reflux for 8-10h, isopropanol was removed azeotropically, evaporation; TLC, elem. anal.;	81%

Shrock-Osborn catalyst (35238-97-2) + dichloromethane (75-09-2) + hydrogen (1333-74-0) + acetone (67-64-1) + acetone semicarbazone (110-20-3) → cis,trans-[RhH2(PPh3)2(acetone semicarbazone)]PF6 * 0.5CH2Cl2

Conditions	Yield
In acetone byproducts: acetone; under Ar; Rh complex treated with H2 (1 atm) in acetone at room temp. for 2.5 h, semicarbazone added, stirred at room temp. for ca. 15 min; evapd. under vac. at room temp., residue dissolved in CH2Cl2, addn. of hexane or Et2O, ppt. collected, dried under vac. overnight; elem. anal.;	78%

MoI(CO)2(NCMe)2(η3-C3H5) + acetone semicarbazone (110-20-3) → MoI(CO)2(Me2CNNHCONH2)(η3-C3H5)

Conditions	Yield
In dichloromethane N2; room temp., equimolar quantities, 15 min;; filtered, washed with Et2O, dried in vacuo, elem. anal.;;	76%

MoI(CO)2(NCMe)2(η3-C3H5) + acetone semicarbazone (110-20-3) → {MoI(CO)2((CH3)2CNNHCONH2)(C3H5)}

Conditions	Yield
In dichloromethane equimolar amts. of educts; pptn. (addn. of Et2O); elem. anal.;	76%

acetone semicarbazone (110-20-3) → 2-imino-5,5-dimethyl-Δ3-1,3,4-oxadiazoline

Conditions	Yield
With lead(IV) acetate; potassium carbonate In dichloromethane for 0.5h;	75%

propan-1-ol-3-amine (156-87-6) + acetone semicarbazone (110-20-3) → acetone 4-(3-hydroxypropyl)semicarbazone (176964-66-2)

Conditions	Yield
In toluene Heating;	60%
In toluene

(2-hydroxyethyl)(methyl)amine (109-83-1) + acetone semicarbazone (110-20-3) → acetone 4-(2-hydroxyethyl)-4-methylsemicarbazone

Conditions	Yield
In toluene Heating;	60%
In toluene Heating;

oxalyl dichloride (79-37-8) + acetone semicarbazone (110-20-3) → 1-(Dimethyleneamino)imidazole-2,4,5-(1H,3H)-trione

Conditions	Yield
In diethyl ether at 20℃; for 4h; Cyclization;	60%

Co(II) chloride hydrate + acetone semicarbazone (110-20-3) → Co((CH3)2CNNHCONH2)2Br2 (86743-59-1)

Conditions	Yield
With HBr In ethanol; water hot EtOH/H2O soln. of salt mixed with EtOH soln. of ligand, excess of HBr added, mixt. refluxed until brown fumes ceased to come out; concd., cooled, filtered out, washed with 50% EtOH, dried at 60°C; elem. anal.;	60%

2-amino-phenol (95-55-6) + acetone semicarbazone (110-20-3) → C10H13N3O2 (211796-39-3)

Conditions	Yield
In toluene for 8.5h; Heating;	59%

{WI(carbonyl)(acetonitrile)(dppm)(eta.2-but-2-yne)}{tetrafluoroborate} (126109-21-5, 125962-97-2, 135267-73-1) + acetone semicarbazone (110-20-3) → WI(CO)((CH3)2CNNHCONH2)(((C6H5)2P)2CH2)(CH3C2CH3)(1+)*BF4(1-) = (C34H37IN3O2P2W)(BF4)

Conditions	Yield
In dichloromethane N2 atmosphere; addn. of org. compd. to soln. of W-compd. in CH2Cl2 with stirring (N2 stream),reacting (3 h); filtration, partial evapn. (vac.), pptn. on dropwise addn. of Et2O, recrystn. (CH2Cl2/Et2O); elem. anal.;	59%

[{Ir(μ-Cl)(2-(p-tolyl)pyridinato)2}2] + chloroform (67-66-3) + acetone semicarbazone (110-20-3) → [Ir(2-(p-tolyl)pyridinato)2(acetone semicarbazone(-1H))]*2H2O

Conditions	Yield
Stage #1: [{Ir(μ-Cl)(2-(p-tolyl)pyridinato)2}2]; acetone semicarbazone With sodium methylate In methanol; dichloromethane at 20℃; for 3h; Stage #2: chloroform	58%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + acetone semicarbazone (110-20-3) → 5-methyl-1H-pyrazole-4-carbaldehyde (112758-40-4)

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.25h; Stage #2: acetone semicarbazone at 70℃; for 4h; Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages;	52.1%

1,1,2,2,-tetracyanoethane (14778-29-1) + acetone semicarbazone (110-20-3) → (5-Amino-3,3,4-tricyano-2,2-dimethyl-2,3-dihydro-pyrrol-1-yl)-urea (140867-53-4)

Conditions	Yield
In N,N-dimethyl-formamide	50%

Cyclohexyl isocyanide (931-53-3) + Benzoylformic acid (611-73-4) + acetone semicarbazone (110-20-3) → N-cyclohexyl-2-[N'-carbamoyl-N-(2-oxo-2-phenylacetyl)hydrazino]isobutyramide

Conditions	Yield
In methanol at 20℃; for 72h; Ugi reaction;	50%

ammonium thiocyanate + Co(II) chloride hydrate + acetone semicarbazone (110-20-3) → Co((CH3)2CNNHCONH2)2(NCS)2 (86743-61-5)

Conditions	Yield
In ethanol; water hot EtOH/H2O soln. of salt mixed with EtOH soln. of ligand, excess of ammonium thiocyanate soln. in H2O added, mixt. refluxed for 3 h; cooled, filtered out, washed with 50% EtOH, dried at 60°C; elem. anal.;	50%

Co(II) chloride hydrate + acetone semicarbazone (110-20-3) → Co((CH3)2CNNHCONH2)2Cl2 (86743-58-0)

Conditions	Yield
In ethanol; water hot EtOH/H2O soln. of salt mixed with EtOH soln. of ligand, mixt. refluxed for ca. 1 h; cooled, filtered out, washed with 50% EtOH, dried at 60°C; elem. anal.;	50%

cobalt(II) sulfate hexahydrate + acetone semicarbazone (110-20-3) → Co((CH3)2CNNHCONH2)2SO4 (86743-60-4)

Conditions	Yield
With H2SO4 In ethanol; water Co salt dissolved in min. H2O, few drops of concd. H2SO4 added, heated to 80°C, hot EtOH soln. of ligand added, soln. refluxed for ca. 3 h; concd., cooled, filtered, washed with 50% EtOH, dried at 60°C; elem. anal.;	50%

chromium(III) nitrate hexahydrate + acetone semicarbazone (110-20-3) → Cr(OC(NH2)NHNC(CH3)2)2NO3(2+)*2NO3(1-)=Cr(OC(NH2)NHNC(CH3)2)2(NO3)3

Conditions	Yield
In ethanol hot ethanolic chromium salt was mixed with hot ethanolic ligand, mixt. was refluxed on a waterbath for about 4 h; mixt. was concd., cooled overnight, crystalls were filtered, washed with aq. EtOH, dried at ca. 60°C; elem. anal.;	50%

phosphonic acid diethyl ester (762-04-9) + acetone semicarbazone (110-20-3) → diethyl [1-(2-carbamoylhydrazino)-1-methylethyl]phosphonate (1415724-69-4)

Conditions	Yield
With tetra[tert-butylphthalocyanine]aluminum chloride at 80℃; for 20h; Inert atmosphere;	50%

Cyclohexyl isocyanide (931-53-3) + p-methoxybenzoylformic acid (7099-91-4) + acetone semicarbazone (110-20-3) → N-cyclohexyl-2-[N'-carbamoyl-N-(2-oxo-2-{p-methoxy}phenylacetyl)hydrazino]isobutyramide (898261-58-0)

Conditions	Yield
In methanol at 20℃; for 72h; Ugi reaction;	48%

chromium chloride hexahydrate + acetone semicarbazone (110-20-3) → Cr(OC(NH2)NHNC(CH3)2)2Cl2(1+)*Cl(1-)=Cr(OC(NH2)NHNC(CH3)2)2Cl3 (84147-76-2)

Conditions	Yield
In ethanol hot ethanolic chromium salt was mixed with hot ethanolic ligand, mixt. was refluxed on a waterbath for about 4 h; mixt. was concd., cooled overnight, crystalls were filtered, washed with aq. EtOH, dried at ca. 60°C; elem. anal.;	45%

oxalyl dichloride (79-37-8) + acetone semicarbazone (110-20-3) → 1-Aminoimidazole-2,4,5-(1H,3H)-trione (133559-55-4)

Conditions	Yield
In benzene for 4h; Cyclization; Heating;	35%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + acetone semicarbazone (110-20-3) → 3-methyl-1H-pyrazole-4-carbaldehyde (112758-40-4)

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 1.5h; Stage #2: acetone semicarbazone at 0 - 70℃; Stage #3: With sodium hydroxide In water Cooling with ice;	32%
With sodium hydroxide; trichlorophosphate 1.) 60 deg C, 4 h, 2.) from 50 deg C to 60 deg C, 5 min; Yield given. Multistep reaction;

acetone semicarbazone (110-20-3) → 4-methyl-1,2,3-selenadiazole (30318-89-9)

Conditions	Yield
With selenium(IV) oxide; acetic acid for 20h;	17%
With selenium(IV) oxide In acetic acid

piperidine (110-89-4) + toluene (108-88-3) + acetone semicarbazone (110-20-3) → piperidine-1-carboxylic acid isopropylidenehydrazide (876472-00-3)

Conditions	Yield
Erhitzen unter Ausschluss von Feuchtigkeit;

Upstream product

• 4426-72-6 hydrazine carboxamide 
• 67-64-1 acetone 
• 22123-17-7 4-isopropylidene-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 14869-57-9 1-isopropyl semicarbazide 
• 7722-84-1 dihydrogen peroxide 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 
• 563-41-7 semicarbazide hydrochloride 
• 127-08-2 potassium acetate 
• 627-70-3 propan-2-one azine 
• 76973-30-3 5-Methyl-4-(1-methylethylidene)-2-(4'-nitrophenyl)-2,4-dihydro-3H-pyrazol-3-one 
• 85921-22-8 5-Methyl-4-(1-methylethylidene)-2-(4'-methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-one 
• 108161-18-8 5-Methyl-4-(1-methylethylidene)-2-(4'-chlorophenyl)-2,4-dihydro-3H-pyrazol-3-one 

Downstream Products

• 64341-20-4 4-pyridin-2-ylsemicarbazide 
• 59-87-0 nitrofurazone 
• 62774-59-8 N-(4-methoxyphenyl)hydrazinecarboxamide 
• 3232-84-6 urazole 
• 64-17-5 ethanol 
• 471-46-5 Oxalamide 
• 627-70-3 propan-2-one azine 
• 17433-87-3 acetone-[4-(4-nitro-phenyl)-semicarbazone] 
• 101435-73-8 acetone-[4-(4-phenylazo-phenyl)-semicarbazone] 
• 78002-37-6 acetone 4-phenylsemicarbazone 
• 537-47-3 4-phenyl-semicarbazide 
• 102-07-8 bis(diphenyl)urea 
• 110-21-4 hydrazodicarboxamide 
• 873386-37-9 1-isopropylidene-5-phenyl carbonohydrazide 

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Relevant articles and documents

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Cyclization of the semicarbazones to 1,3,4-oxadiazole derivatives using ceric ammonium nitrate as oxidant

Cyclization of the semicarbazones to 1,3,4-oxadiazole using ceric ammonium nitrate as oxidant was studied. 2-Imino-1,3,4-oxadiazolines can be produced from semicarbazones, which undergo thermolysis to amides. Benzoic acid benzylidene hydrazide can also be cyclized to 2-methoxy-2-phenyl-1,3,4-oxadiazole in the presence of ceric ammonium nitrate and methanol.

Reactions of diazoalkanes with isocyanates. Synthesis of imidazolidine-2,4-diones, oxindoles, and oxazolidinones

Thermolysis of a 5,5-dialkyl-Δ3-1,3,4-oxadiazolin-2-one in nitrobenzene containing an aryl isocyanate at 150 deg C affords a 1,3-diaryl-5,5-dialkyl imidazolidine-2,4-dione, an N-arylcarbamoyl-3,3-dialkyloxindole, and a 3-aryl-2-arylimino-5,5-dialkyl-1,3-oxazolidin-4-one.Those products arise from attack of a diazoalkane, generated in situ from the oxadiazolinone by thermal cycloreversion, on the isocyanate function.Two imidazolidine diones, three oxazolidinones, and 14 oxindoles were prepared.