Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium carbonate; ammonium chloride In water at 60℃; for 5h; | 99.6% |
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water for 24h; Heating; | 96% |
With dihydroxylamine phosphate; potassium hydrogencarbonate In water at 39℃; for 1.83333h; Temperature; | 96% |
2-nitropropane
3-diazo-5-phenyl-3H-1,2,4-triazole
A
benzonitrile
B
acetone oxime
Conditions | Yield |
---|---|
at 80℃; Yields of byproduct given; | A n/a B 98% |
2-chloro-2-nitrosopropane
3-allyl-1,1-diethyl-thiourea
2,4,6-Trinitrophenol
B
acetone oxime
Conditions | Yield |
---|---|
In hydrogenchloride; ethanol at 20℃; for 1h; Cyclization; | A 89% B n/a |
2,4-dinitrophenyl ether of acetone oxime
N-butylamine
A
2,4-dinitro-N-butylaniline
B
acetone oxime
Conditions | Yield |
---|---|
In dichloromethane Product distribution; 0 deg C, 72 h; 20 deg C, 48 h; | A 80% B 62% |
Conditions | Yield |
---|---|
With hydroxylamine; oxygen In ethanol under 760.051 Torr; for 2h; Catalytic behavior; Reflux; Green chemistry; | 65% |
Allylthiourea
2-chloro-2-nitrosopropane
2,4,6-Trinitrophenol
B
acetone oxime
Conditions | Yield |
---|---|
In hydrogenchloride; ethanol at 20℃; for 1h; Cyclization; | A 64% B n/a |
2-chloro-2-nitrosopropane
1-allyl-3-phenyl-thiourea
2,4,6-Trinitrophenol
B
acetone oxime
Conditions | Yield |
---|---|
In hydrogenchloride; ethanol at 20℃; for 1h; Cyclization; | A 60% B n/a |
(E)-4-methoxybenzaldoxime
β-naphthaldehyde
A
4-methoxy-benzaldehyde
B
acetone oxime
Conditions | Yield |
---|---|
With perchloric acid In dichloromethane; water at 23℃; for 24h; Inert atmosphere; | A 38% B 33% |
N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine
A
3,4-Dihydro-3,3,4,4-tetramethyl-1,2-diazete 1,2-dioxide
B
acetone oxime
Conditions | Yield |
---|---|
With tert-butylhypochlorite In dichloromethane at 20℃; for 2h; | A n/a B 31% |
Conditions | Yield |
---|---|
In dichloromethane Product distribution; 0 deg C, 72 h; 20 deg C, 48 h; | 29% |
syn-benzaldehyde oxime
acetone
A
benzaldehyde
B
acetone oxime
Conditions | Yield |
---|---|
With perchloric acid In water; water-d2 at 23℃; for 24h; Inert atmosphere; | A n/a B 29% |
(E)-4-(trifluoromethyl)benzaldoxime
β-naphthaldehyde
A
4-Trifluoromethylbenzaldehyde
B
acetone oxime
Conditions | Yield |
---|---|
With perchloric acid In dichloromethane; water at 23℃; for 24h; Inert atmosphere; | A 15% B 9% |
diethyl ether
2-chloro-2-nitrosopropane
dimethyl zinc(II)
A
methane
B
N-Methylhydroxylamine
C
acetone
D
acetone oxime
diethyl ether
2-bromo-2-nitroso-propane
diethylzinc
A
acetone
B
1-bromoacetone
C
ethylhydroxylamine
D
acetone oxime
Conditions | Yield |
---|---|
Produkte sind noch Aethan und Aethylen; |
2-nitropropane
N,N,N',N'-tetramethyl-C-phenylmethanediamine
A
N,N-dimethylbenzamide
B
acetone oxime
Conditions | Yield |
---|---|
at 120 - 130℃; |
Conditions | Yield |
---|---|
With diethyl ether; alkyl magnesium halide | |
With diethyl ether; aryl magnesium halide | |
With diethyl ether; zinc dialkyl |
Conditions | Yield |
---|---|
With diethyl ether; ammonia | |
With diethyl ether; alkyl magnesium halide | |
With diethyl ether; zinc dialkyl | |
With diethyl ether; aryl magnesium halide |
Conditions | Yield |
---|---|
With methanol; palladium Hydrogenation; | |
With methanol; palladium Hydrogenation; |
Conditions | Yield |
---|---|
With diethyl ether; hydroxylamine | |
With diammonium sulfide; diethyl ether | |
With diethyl ether; potassium hydrosulfide | |
With diethyl ether; aluminium amalgam |
Conditions | Yield |
---|---|
With ethanol; hydroxylamine hydrochloride |
Conditions | Yield |
---|---|
With water; hydroxylamine |
p-toluene sulfinic acid
toluene-4-sulfonamide
toluene-4-sulfinic acid ; ammonium salt
A
syn-benzaldehyde oxime
B
acetone oxime
Conditions | Yield |
---|---|
Verschmelzenden; |
Conditions | Yield |
---|---|
With caro's acid; magnesium oxide | |
With sodium tungstate; dihydrogen peroxide |
ethyl nitrite
ethanol
sodium ethanolate
phenyl isopropyl ketone
A
sodium benzoate
B
benzoic acid ethyl ester
C
acetone oxime
2-nitropropane
2-Methoxynaphthalene
A
2-chloro-2-nitrosopropane
B
1-chloro-2-methoxynaphthalene
C
acetone
D
acetone oxime
Conditions | Yield |
---|---|
With pyridine hydrochloride Product distribution; Heating; |
Conditions | Yield |
---|---|
With Trimethyl(methylthio)silane; potassium hydride 1) THF, rt, 1 h, 2) rt, 48 h; Yield given. Multistep reaction; |
2-hydroxyamino-propan-2-ol
acetone oxime
Conditions | Yield |
---|---|
In methanol; water at 25℃; Rate constant; |
N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine
acetone oxime
Conditions | Yield |
---|---|
With air at 20 - 25℃; for 168h; | 0.97 g |
N-(2-hydroxy-1,1-dimethyl-2-phenylethyl)hydroxylamine
A
benzaldehyde
B
acetone oxime
Conditions | Yield |
---|---|
In water at 25℃; Product distribution; Mechanism; buffer of pH 8.8, controlled potential electrolysis; further N-alkylhydroxylamines with a β-hydroxy group; |
Conditions | Yield |
---|---|
toluene-4-sulfonic acid at 50℃; for 1h; Beckmann rearrangement; | 100% |
With bismuth(III) chloride for 0.166667h; Beckmann rearrangement; microwave irradiation; | 90% |
With indium(III) triflate In acetonitrile for 2h; Beckmann rearrangement; Heating; | 90% |
N-methoxy-N-methyl-2-phenylacetamide
acetone oxime
Conditions | Yield |
---|---|
Stage #1: N-methoxy-N-methyl-2-phenylacetamide; acetone oxime With n-butyllithium In tetrahydrofuran at 0℃; Stage #2: With sulfuric acid In tetrahydrofuran; water for 1h; Heating; | 100% |
With n-butyllithium; sulfuric acid 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, reflux, 1 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With pyridine; di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 20h; | 100% |
With dicyclohexyl-carbodiimide |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In diethyl ether at 20℃; for 0.5h; | 100% |
acetone oxime
Conditions | Yield |
---|---|
In toluene at 60℃; for 2h; | 100% |
bis(tri-n-butyltin)oxide
acetone oxime
Isopropylidenaminooxy-tributyl-stannan
Conditions | Yield |
---|---|
In toluene 1:2; azeotropic dehydration; 2 h; | 100% |
In benzene 1:2; azeotropic dehydration; 2 h; | 100% |
In benzene 1:2; azeotropic dehydration; 2 h; | 100% |
1-{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}ethanone
acetone oxime
1-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-3-fluoro-2-(propan-2-ylideneaminooxy)phenyl)ethanone
Conditions | Yield |
---|---|
Stage #1: acetone oxime With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.75h; Stage #2: 1-{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}ethanone In tetrahydrofuran at 20℃; for 3h; | 100% |
Stage #1: acetone oxime With potassium tert-butylate In tetrahydrofuran at 18 - 25℃; for 0.75h; Stage #2: 1-{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}ethanone In tetrahydrofuran for 3h; Stage #3: With water; ammonium chloride In tetrahydrofuran |
5-bromo-3-fluoropyridine-2-carbonitrile
acetone oxime
3,5-bis-isopropylideneaminooxypyridine-2-carbonitrile
Conditions | Yield |
---|---|
Stage #1: acetone oxime With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #2: 5-bromo-3-fluoropyridine-2-carbonitrile In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; | 100% |
bis(N-phenylsalicylideneiminato)aluminium(III)di(μ-isopropoxo)di(isopropoxo) aluminium(III)
acetone oxime
Conditions | Yield |
---|---|
In benzene byproducts: C3H7OH; under strictly unhydrous conditions; in 1:2 molar ratio (Al-complex:(CH3)2CNOH in refluxing unhydrous C6H6 for 4 h, C3H7OH fractionated azeotropically with C6H6; excess solvent stripped off under reduced pressure, recrystd. (C6H6/C6H14); elem. anal., detd. by IR, NMR; | 99.5% |
acetone oxime
Conditions | Yield |
---|---|
Stage #1: acetone oxime With trifluoromethylsulfonic anhydride; triethylamine In toluene at -78℃; for 0.0833333h; Stage #2: methyl cyanoacetate sodium enolate In toluene at -78 - 20℃; for 1h; | 99% |
Stage #1: acetone oxime With trifluoromethanesulfonic acid anhydride; triethylamine In toluene at -78℃; for 0.0833333h; Stage #2: methyl cyanoacetate sodium enolate In tetrahydrofuran; toluene at -78 - 20℃; | 99% |
bis(N-phenylsalicylideneiminato)aluminium(III)di(μ-isopropoxo)di(isopropoxo) aluminium(III)
acetone oxime
Conditions | Yield |
---|---|
In benzene byproducts: C3H7OH; under strictly unhydrous conditions; in 1:1 molar ratio (Al-complex:(CH3)2CNOH in refluxing unhydrous C6H6 for 4 h, C3H7OH fractionated azeotropically with C6H6; excess solvent stripped off under reduced pressure, recrystd. (C6H6/C6H14); elem. anal., detd. by IR, NMR; | 99% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 99% |
Conditions | Yield |
---|---|
Stage #1: acetone oxime With potassium hydroxide; lithium hydroxide In N,N-dimethyl acetamide; water at 50℃; Stage #2: benzyl chloride In N,N-dimethyl acetamide; water at 62℃; for 2.25h; | 98.96% |
With ethanol; sodium | |
With sodium In ethanol at 25℃; Inert atmosphere; | 10.9 g |
Conditions | Yield |
---|---|
Stage #1: acetone oxime With potassium hydroxide; lithium hydroxide In N,N-dimethyl acetamide; water at 50℃; Stage #2: p-bromobenzyl chloride In N,N-dimethyl acetamide; water at 65℃; for 2.25h; | 98.28% |
Conditions | Yield |
---|---|
Stage #1: acetone oxime With potassium hydroxide; lithium hydroxide In N,N-dimethyl acetamide; water at 55℃; Stage #2: 2,4-Dichlorobenzyl chloride In N,N-dimethyl acetamide; water at 60℃; for 2.33333h; | 98.25% |
Conditions | Yield |
---|---|
With sodium methylate at 70℃; under 760.051 Torr; for 8h; Temperature; Reagent/catalyst; Large scale; | 98.2% |
Conditions | Yield |
---|---|
With sodium methylate at 130℃; under 37.5038 Torr; for 4h; Time; Large scale; | 98.2% |
acetone oxime
Conditions | Yield |
---|---|
With HCl In methanol addn. of methanolic soln. of HCl to mixt. of Mo compd. and oxime, stirred at room temp. for 7 h, pptn.; filtered off, washed (Et2O); | 98% |
(η6-1-fluoro-3-methylbenzene)tricarbonylchromium(0)
tetraoctyl ammonium bromide
acetone oxime
(CO)3CrC6H4(CH3)ONC(CH3)2
Conditions | Yield |
---|---|
With potassium hydroxide In benzene (N2), stirred for 1 h; solvent removed under vac., residue dissolved in Et2O, filtered on Celite, evaporated, crystd. from di-isopropyl ether; | 98% |
Conditions | Yield |
---|---|
Stage #1: acetone oxime With potassium hydroxide; lithium hydroxide In N,N-dimethyl acetamide; water at 53℃; Stage #2: 1-chloro-2-(chloromethyl)benzene In N,N-dimethyl acetamide; water at 65℃; for 2.16667h; | 97.11% |
Dichloromethylvinylsilane
acetone oxime
bis(isopropylideneaminooxy)methylvinylsilane
Conditions | Yield |
---|---|
In hexane at 30 - 40℃; for 1h; | 97% |
In toluene at 55 - 60℃; for 2h; | 61% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; | 97% |
Conditions | Yield |
---|---|
Stage #1: acetone oxime With potassium hydroxide; lithium hydroxide In N,N-dimethyl acetamide; water at 50℃; Stage #2: 1-Chloro-4-(chloromethyl)benzene In N,N-dimethyl acetamide; water at 60℃; for 2.33333h; | 96.94% |
3-hydroxyphenylglyoxal
2,4,5,6-tetraaminopyrimidine sulfate
acetone oxime
Conditions | Yield |
---|---|
Stage #1: 3-hydroxyphenylglyoxal; acetone oxime With hydrogenchloride In methanol; water at 50℃; for 1h; pH=~ 2 - ~ 3; Stage #2: 2,4,5,6-tetraaminopyrimidine sulfate In water at 20℃; for 9h; Heating / reflux; Stage #3: With water; sodium hydrogencarbonate at 20℃; pH=~ 6 - ~ 7; | 96.5% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium carbonate In methanol at 60℃; under 750.075 Torr; | 96.5% |
4-nitrophenyl N2,N6-bis[(phenylmethoxy)carbonyl]-L-lysinate
acetone oxime
Conditions | Yield |
---|---|
In chloroform Ambient temperature; | 96% |
acetone oxime
O,O-diisopropyl hydrogen phosphorodithioate
S-<1-(hydroxyamino)-1-methylethyl> O,O-diisopropyl phosphorodithioate
Conditions | Yield |
---|---|
In diethyl ether for 3h; | 96% |
The molecular structure of Acetone oxime (CAS NO.127-06-0):
IUPAC Name: N-Propan-2-ylidenehydroxylamine
Molecular Weight: 73.09378 g/mol
Molecular Formula: C3H7NO
Density: 0.91 g/cm3
Melting Point: 60-63 °C(lit.)
Boiling Point: 135 °C at 760 mmHg
Flash Point: 45.2 °C
Index of Refraction: 1.41
Molar Refractivity: 19.9 cm3
Molar Volume: 80.2 cm3
Surface Tension: 25.6 dyne/cm
Enthalpy of Vaporization: 41.09 kJ/mol
Vapour Pressure: 4.65 mmHg at 25 °C
Water Solubility: 330 g/L (20 °C)
XLogP3: 0.1
H-Bond Donor: 1
H-Bond Acceptor: 2
Tautomer Count: 2
Exact Mass: 73.052764
MonoIsotopic Mass: 73.052764
Topological Polar Surface Area: 32.6
Heavy Atom Count: 5
Canonical SMILES: CC(=NO)C
InChI: InChI=1S/C3H7NO/c1-3(2)4-5/h5H,1-2H3
InChIKey: PXAJQJMDEXJWFB-UHFFFAOYSA-N
EINECS: 204-820-1
Product Categories: Pharmaceutical Intermediates; Oximino Silanes; Nitrogen Compounds; Organic Building Blocks; Oximes
Acetone oxime (CAS NO.127-06-0) is used in organic synthesis. It is also used as an analytical reagent for the determination of cobalt.
1. | orl-rat LD:>500 mg/kg | NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. 5 (1953),26. | ||
2. | ipr-mus LD50:4000 mg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 119 (1957),522. |
Reported in EPA TSCA Inventory.
Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
RIDADR: UN1325
WGK Germany: 3
RTECS: AL6825000
F: 21
HazardClass: 4.1
PackingGroup: III
Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx.
Acetone oxime (CAS NO.127-06-0) is also named as 2-Propanone oxime ; 4-01-00-03202 (Beilstein Handbook Reference) ; AI3-52259 ; Acetonoxime ; Acetoxime ; BRN 1560146 ; CCRIS 5 ; NSC 7601 ; beta-Isonitrosopropane . Acetone oxime (CAS NO.127-06-0) is white crystals. It is easily soluble in water, ethanol, ether and acetone, soluble in acid and base.
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