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

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

Used in Pesticide Industry:
Acetone semicarbazone is used as a starting material for the synthesis of Isazophos, which is a pesticide. It serves as a key intermediate in the production process, contributing to the development of Isazophos and its application in agriculture for pest control.

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 
• 563-41-7 semicarbazide hydrochloride 
• 14869-57-9 1-isopropyl semicarbazide 
• 7722-84-1 dihydrogen peroxide 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 
• 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

• 2845-79-6 1-benzoyl semicarbazide 
• 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 
• 110-21-4 hydrazodicarboxamide 
• 3741-86-4 acetone methylphenylhydrazone 
• 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 

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