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127-06-0

Basic Information
CAS No.: 127-06-0
Name: Acetone oxime
Molecular Structure:
Molecular Structure of 127-06-0 (Acetone oxime)
Formula: C3H7NO
Molecular Weight: 73.09
Synonyms: Acetone,oxime (6CI,8CI);Acetoxime;Dimethyl ketoxime;N-Isopropylidenehydroxylamine;NSC 7601;Propanone oxime;b-Isonitrosopropane;2-Propanone, oxime;
EINECS: 204-820-1
Density: 0.91 g/cm3
Melting Point: 60-63 °C(lit.)
Boiling Point: 135 °C at 760 mmHg
Flash Point: 45.2 °C
Solubility: 330 g/L (20 °C) in water
Appearance: white crystals
Hazard Symbols: Xn
Risk Codes:  Xn:Harmful;
">  Xn:Harmful;
Safety: 22-24/25
Transport Information: UN 1325
PSA: 32.59000
LogP: 0.85640
Synthetic route
67-64-1

acetone

127-06-0

acetone oxime

Conditions
ConditionsYield
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%
79-46-9

2-nitropropane

80670-36-6

3-diazo-5-phenyl-3H-1,2,4-triazole

A

100-47-0

benzonitrile

B

127-06-0

acetone oxime

Conditions
ConditionsYield
at 80℃; Yields of byproduct given;A n/a
B 98%
2421-26-3

2-chloro-2-nitrosopropane

21645-26-1

3-allyl-1,1-diethyl-thiourea

88-89-1

2,4,6-Trinitrophenol

A

5-chloromethyl-2-diethylamino-2-thiazoline picrate

B

127-06-0

acetone oxime

Conditions
ConditionsYield
In hydrogenchloride; ethanol at 20℃; for 1h; Cyclization;A 89%
B n/a
13181-10-7

2,4-dinitrophenyl ether of acetone oxime

109-73-9

N-butylamine

A

13059-86-4

2,4-dinitro-N-butylaniline

B

127-06-0

acetone oxime

Conditions
ConditionsYield
In dichloromethane Product distribution; 0 deg C, 72 h; 20 deg C, 48 h;A 80%
B 62%
67-63-0

isopropyl alcohol

127-06-0

acetone oxime

Conditions
ConditionsYield
With hydroxylamine; oxygen In ethanol under 760.051 Torr; for 2h; Catalytic behavior; Reflux; Green chemistry;65%
109-57-9

Allylthiourea

2421-26-3

2-chloro-2-nitrosopropane

88-89-1

2,4,6-Trinitrophenol

A

2-amino-5-chloromethyl-2-thiazoline picrate

B

127-06-0

acetone oxime

Conditions
ConditionsYield
In hydrogenchloride; ethanol at 20℃; for 1h; Cyclization;A 64%
B n/a
2421-26-3

2-chloro-2-nitrosopropane

7341-63-1

1-allyl-3-phenyl-thiourea

88-89-1

2,4,6-Trinitrophenol

A

5-chloromethyl-2-phenylamino-2-thiazoline picrate

B

127-06-0

acetone oxime

Conditions
ConditionsYield
In hydrogenchloride; ethanol at 20℃; for 1h; Cyclization;A 60%
B n/a
66-99-9

β-naphthaldehyde

A

123-11-5

4-methoxy-benzaldehyde

B

127-06-0

acetone oxime

Conditions
ConditionsYield
With perchloric acid In dichloromethane; water at 23℃; for 24h; Inert atmosphere;A 38%
B 33%
14384-45-3

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine

A

34493-89-5

3,4-Dihydro-3,3,4,4-tetramethyl-1,2-diazete 1,2-dioxide

B

127-06-0

acetone oxime

Conditions
ConditionsYield
With tert-butylhypochlorite In dichloromethane at 20℃; for 2h;A n/a
B 31%
13194-03-1

Dimethylketonoximpikrat

109-73-9

N-butylamine

127-06-0

acetone oxime

Conditions
ConditionsYield
In dichloromethane Product distribution; 0 deg C, 72 h; 20 deg C, 48 h;29%
67-64-1

acetone

A

100-52-7

benzaldehyde

B

127-06-0

acetone oxime

Conditions
ConditionsYield
With perchloric acid In water; water-d2 at 23℃; for 24h; Inert atmosphere;A n/a
B 29%
16939-49-4, 24652-60-6, 66046-34-2

(E)-4-(trifluoromethyl)benzaldoxime

66-99-9

β-naphthaldehyde

A

455-19-6

4-Trifluoromethylbenzaldehyde

B

127-06-0

acetone oxime

Conditions
ConditionsYield
With perchloric acid In dichloromethane; water at 23℃; for 24h; Inert atmosphere;A 15%
B 9%
60-29-7

diethyl ether

2421-26-3

2-chloro-2-nitrosopropane

544-97-8

dimethyl zinc(II)

A

34557-54-5

methane

B

593-77-1

N-Methylhydroxylamine

C

67-64-1

acetone

D

127-06-0

acetone oxime

60-29-7

diethyl ether

7119-91-7

2-bromo-2-nitroso-propane

557-20-0

diethylzinc

A

67-64-1

acetone

B

598-31-2

1-bromoacetone

C

624-81-7

ethylhydroxylamine

D

127-06-0

acetone oxime

Conditions
ConditionsYield
Produkte sind noch Aethan und Aethylen;
79-46-9

2-nitropropane

13880-55-2

N,N,N',N'-tetramethyl-C-phenylmethanediamine

A

611-74-5

N,N-dimethylbenzamide

B

127-06-0

acetone oxime

Conditions
ConditionsYield
at 120 - 130℃;
2421-26-3

2-chloro-2-nitrosopropane

127-06-0

acetone oxime

Conditions
ConditionsYield
With diethyl ether; alkyl magnesium halide
With diethyl ether; aryl magnesium halide
With diethyl ether; zinc dialkyl
7119-91-7

2-bromo-2-nitroso-propane

127-06-0

acetone oxime

Conditions
ConditionsYield
With diethyl ether; ammonia
With diethyl ether; alkyl magnesium halide
With diethyl ether; zinc dialkyl
With diethyl ether; aryl magnesium halide
594-71-8

2-chloro-2-nitro-propane

127-06-0

acetone oxime

Conditions
ConditionsYield
With methanol; palladium Hydrogenation;
With methanol; palladium Hydrogenation;
5275-46-7

2-nitro-2-nitrosopropane

127-06-0

acetone oxime

Conditions
ConditionsYield
With diethyl ether; hydroxylamine
With diammonium sulfide; diethyl ether
With diethyl ether; potassium hydrosulfide
With diethyl ether; aluminium amalgam
103-02-6

acetone phenylhydrazone

127-06-0

acetone oxime

Conditions
ConditionsYield
With ethanol; hydroxylamine hydrochloride
540-92-1

acetone sodium bisulfite

127-06-0

acetone oxime

Conditions
ConditionsYield
With water; hydroxylamine
536-57-2

p-toluene sulfinic acid

70-55-3

toluene-4-sulfonamide

57267-72-8

toluene-4-sulfinic acid ; ammonium salt

B

127-06-0

acetone oxime

Conditions
ConditionsYield
Verschmelzenden;
75-31-0

isopropylamine

127-06-0

acetone oxime

Conditions
ConditionsYield
With caro's acid; magnesium oxide
With sodium tungstate; dihydrogen peroxide
109-95-5

ethyl nitrite

64-17-5

ethanol

141-52-6

sodium ethanolate

611-70-1

phenyl isopropyl ketone

A

532-32-1

sodium benzoate

B

93-89-0

benzoic acid ethyl ester

C

127-06-0

acetone oxime

79-46-9

2-nitropropane

93-04-9

2-Methoxynaphthalene

A

2421-26-3

2-chloro-2-nitrosopropane

B

13101-92-3

1-chloro-2-methoxynaphthalene

C

67-64-1

acetone

D

127-06-0

acetone oxime

Conditions
ConditionsYield
With pyridine hydrochloride Product distribution; Heating;
79-46-9

2-nitropropane

127-06-0

acetone oxime

Conditions
ConditionsYield
With Trimethyl(methylthio)silane; potassium hydride 1) THF, rt, 1 h, 2) rt, 48 h; Yield given. Multistep reaction;
61558-18-7

2-hydroxyamino-propan-2-ol

127-06-0

acetone oxime

Conditions
ConditionsYield
In methanol; water at 25℃; Rate constant;
14384-45-3

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine

127-06-0

acetone oxime

Conditions
ConditionsYield
With air at 20 - 25℃; for 168h;0.97 g
68385-34-2

N-(2-hydroxy-1,1-dimethyl-2-phenylethyl)hydroxylamine

A

100-52-7

benzaldehyde

B

127-06-0

acetone oxime

Conditions
ConditionsYield
In water at 25℃; Product distribution; Mechanism; buffer of pH 8.8, controlled potential electrolysis; further N-alkylhydroxylamines with a β-hydroxy group;
127-06-0

acetone oxime

79-16-3

N-methyl-acetamide

Conditions
ConditionsYield
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%
95092-10-7

N-methoxy-N-methyl-2-phenylacetamide

127-06-0

acetone oxime

3-Methyl-5-(phenylmethyl)isoxazole

Conditions
ConditionsYield
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;
1142-20-7

N-Cbz-Ala

127-06-0

acetone oxime

24125-33-5

N-benzyloxycarbonyl L-alanine acetoxime ester

Conditions
ConditionsYield
With pyridine; di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 20h;100%
With dicyclohexyl-carbodiimide
123-76-2

levulinic acid

127-06-0

acetone oxime

647834-80-8

O-levulinyl acetonoxime

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In diethyl ether at 20℃; for 0.5h;100%

α-isocyanatomethylmethyldimethoxysilane

127-06-0

acetone oxime

{[dimethoxy(methyl)silyl]methyl}carbamoyldimethylketonoxime

Conditions
ConditionsYield
In toluene at 60℃; for 2h;100%
56-35-9

bis(tri-n-butyltin)oxide

127-06-0

acetone oxime

10218-32-3

Isopropylidenaminooxy-tributyl-stannan

Conditions
ConditionsYield
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%
914935-38-9

1-{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}ethanone

127-06-0

acetone oxime

1223444-75-4

1-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-3-fluoro-2-(propan-2-ylideneaminooxy)phenyl)ethanone

Conditions
ConditionsYield
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
886373-28-0

5-bromo-3-fluoropyridine-2-carbonitrile

127-06-0

acetone oxime

1448674-24-5

3,5-bis-isopropylideneaminooxypyridine-2-carbonitrile

Conditions
ConditionsYield
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%
443286-95-1

bis(N-phenylsalicylideneiminato)aluminium(III)di(μ-isopropoxo)di(isopropoxo) aluminium(III)

127-06-0

acetone oxime

bis(N-phenylsalicylideneiminato)aluminium(III)di(μ-isopropoxo)di(isopropoxo) aluminium(III)

Conditions
ConditionsYield
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%

methyl cyanoacetate sodium enolate

127-06-0

acetone oxime

2-cyano-3-methylaminobut-2-enoic acid methyl ester

Conditions
ConditionsYield
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%
443286-95-1

bis(N-phenylsalicylideneiminato)aluminium(III)di(μ-isopropoxo)di(isopropoxo) aluminium(III)

127-06-0

acetone oxime

bis(N-phenylsalicylideneiminato)aluminium(III)di(μ-isopropoxo)aluminium(III)(isopropoxo)(ONC(CH3)2)

Conditions
ConditionsYield
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%
506-30-9

Arachidic acid

127-06-0

acetone oxime

1544620-07-6

eicosanoic acid acetoxime ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;99%
100-44-7

benzyl chloride

127-06-0

acetone oxime

3376-36-1

acetone O-benzyloxime

Conditions
ConditionsYield
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
589-17-3

p-bromobenzyl chloride

127-06-0

acetone oxime

O-(p-bromobenzyl)acetoxime

Conditions
ConditionsYield
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%
94-99-5

2,4-Dichlorobenzyl chloride

127-06-0

acetone oxime

O-(o,p-dichlorobenzyl)acetoxime

Conditions
ConditionsYield
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%
554-12-1

propanoic acid methyl ester

127-06-0

acetone oxime

O-propanoyl acetone oxime

Conditions
ConditionsYield
With sodium methylate at 70℃; under 760.051 Torr; for 8h; Temperature; Reagent/catalyst; Large scale;98.2%
590-01-2

propionic acid butyl ester

127-06-0

acetone oxime

O-propanoyl acetone oxime

Conditions
ConditionsYield
With sodium methylate at 130℃; under 37.5038 Torr; for 4h; Time; Large scale;98.2%

2N(C4H9)4(1+)*Mo4O12((CH3)2CNO)2(2-)={N(C4H9)4}2{Mo4O12((CH3)2CNO)2}

127-06-0

acetone oxime

Mo4O10(OCH3)4((CH3)2CNHO)2

Conditions
ConditionsYield
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%
33411-10-8

(η6-1-fluoro-3-methylbenzene)tricarbonylchromium(0)

14866-33-2

tetraoctyl ammonium bromide

127-06-0

acetone oxime

97932-55-3

(CO)3CrC6H4(CH3)ONC(CH3)2

Conditions
ConditionsYield
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%
611-19-8

1-chloro-2-(chloromethyl)benzene

127-06-0

acetone oxime

O-(o-chlorobenzyl)acetoxime

Conditions
ConditionsYield
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%
124-70-9

Dichloromethylvinylsilane

127-06-0

acetone oxime

73160-13-1

bis(isopropylideneaminooxy)methylvinylsilane

Conditions
ConditionsYield
In hexane at 30 - 40℃; for 1h;97%
In toluene at 55 - 60℃; for 2h;61%
57-10-3

1-hexadecylcarboxylic acid

127-06-0

acetone oxime

139745-12-3

acetone oxime palmitate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;97%
104-83-6

1-Chloro-4-(chloromethyl)benzene

127-06-0

acetone oxime

O-(p-chlorobenzyl)acetoxime

Conditions
ConditionsYield
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%
70935-14-7

3-hydroxyphenylglyoxal

5392-28-9

2,4,5,6-tetraaminopyrimidine sulfate

127-06-0

acetone oxime

TG100110

Conditions
ConditionsYield
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%
127-06-0

acetone oxime

79-46-9

2-nitropropane

Conditions
ConditionsYield
With dihydrogen peroxide; sodium carbonate In methanol at 60℃; under 750.075 Torr;96.5%
21160-82-7

4-nitrophenyl N2,N6-bis[(phenylmethoxy)carbonyl]-L-lysinate

127-06-0

acetone oxime

Nα,Nε-dibenzyloxycarbonyl L-lysine acetoxime ester

Conditions
ConditionsYield
In chloroform Ambient temperature;96%
127-06-0

acetone oxime

107-56-2

O,O-diisopropyl hydrogen phosphorodithioate

75320-62-6

S-<1-(hydroxyamino)-1-methylethyl> O,O-diisopropyl phosphorodithioate

Conditions
ConditionsYield
In diethyl ether for 3h;96%
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    Acetone oxime

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    127-06-0

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    Product Name: Acetone oxime CAS: 127-06-0 MF: C3H7NO MW: 73.09 EINECS: 204-820-1 Mol File: 127-06-0.mol Acetone oxime Structure Acetone oxime Chemical Properties Melting point 60-63 °C(lit.) Boiling point 135 °C(li

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    127-06-0

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Chemistry

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

Uses

 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.

Toxicity Data With Reference

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.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

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.

Specification

 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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