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Basic Information
CAS No.: 127-06-0
Name: Acetone oxime
Article Data: 130
Molecular Structure:
Molecular Structure of 127-06-0 (Acetone oxime)
Formula: C3H7NO
Molecular Weight: 73.0947
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%
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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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