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Acetone oxime information


Acetone oxime
Names
Preferred IUPAC name
N-Hydroxypropan-2-imine
Other names
Acetoxime; N-Hydroxy-2-propanimine; Methyl methyl ketoxime; 2-Propanone oxime
Identifiers
CAS Number
  • 127-06-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15349
ChemSpider
  • 60524
ECHA InfoCard 100.004.383 Edit this at Wikidata
EC Number
  • 204-820-1
KEGG
  • C01995
PubChem CID
  • 67180
UNII
  • QX74TFD64T checkY
CompTox Dashboard (EPA)
  • DTXSID6020010 Edit this at Wikidata
InChI
  • InChI=1S/C3H7NO/c1-3(2)4-5/h5H,1-2H3
    Key: PXAJQJMDEXJWFB-UHFFFAOYSA-N
  • InChI=1/C3H7NO/c1-3(2)4-5/h5H,1-2H3
    Key: PXAJQJMDEXJWFB-UHFFFAOYAK
SMILES
  • CC(=NO)C
Properties
Chemical formula
C3H7NO
Molar mass 73.095 g·mol−1
Appearance White needle like crystals
Density 0.901 g/mL[1]
Melting point 60 to 63 °C (140 to 145 °F; 333 to 336 K)
Boiling point 135 °C (275 °F; 408 K)
Solubility in water
330 g/L (20 °C)
Magnetic susceptibility (χ)
-44.42·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
May be harmful if swallowed
GHS labelling:
Pictograms
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Signal word
Danger
Hazard statements
H228, H302, H317, H318, H351
Precautionary statements
P201, P202, P210, P240, P241, P261, P264, P270, P272, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P310, P321, P330, P333+P313, P363, P370+P378, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
0
0
Flash point 60 °C (140 °F; 333 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
4,000 mg/kg Intraperitoneal-mouse
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Acetone oxime (acetoxime) is the organic compound with the formula (CH3)2CNOH. It is the simplest example of a ketoxime. It is a white crystalline solid that is soluble in water, ethanol, ether, chloroform, and ligroin. It is used as a reagent in organic synthesis.[2]

Acetone oxime (acetoxime) was first prepared and named in 1882 by the German chemist Victor Meyer and his Swiss student Alois Janny.[3]

  1. ^ Sigma-Aldrich Chemical Catalogue "Acetone Oxime". Retrieved 2 September 2016.
  2. ^ Steven M. Weinreb, Kristina Borstnik "Acetone Oxime" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2007. doi:10.1002/047084289X.rn00765
  3. ^ Meyer, Victor; Janny, Alois (1882). "Ueber die Einwirkung von Hydroxylamin auf Aceton" [On the effect of hydroxylamine on acetone]. Berichte der Deutschen Chemischen Gesellschaft (in German). 15: 1324–1326. doi:10.1002/cber.188201501285. From p. 1324: "Die Substanz, welche wir, wegen ihrer nahen Beziehungen zur Acetoximsäure, und da sie keine sauren Eigenschaften besitzt, vorläufig Acetoxim nennen wollen, …" (The substance, which we – on account of its close relations to acetoximic acid, and since it possesses no acid properties – will, for the present, name "acetoxime," … )

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Acetone oxime

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Acetone oxime (acetoxime) is the organic compound with the formula (CH3)2CNOH. It is the simplest example of a ketoxime. It is a white crystalline solid...

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Oxime

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In organic chemistry, an oxime is an organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and...

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Oximinotransferase

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oxime + acetone ⇌ {\displaystyle \rightleftharpoons } pyruvate + acetone oxime Thus, the two substrates of this enzyme are pyruvate oxime and acetone...

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Functional group

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Nitroso RNO nitroso- (Nitrosyl-)   Nitrosobenzene Oxime Oxime RCH=NOH   Oxime Acetone oxime (2-Propanone oxime) Pyridine derivative Pyridyl RC5H4N 4-pyridyl...

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C3H7NO

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The molecular formula C3H7NO may refer to: Acetone oxime (acetoxime) 1-Amino-2-propanone Dimethylformamide Isoxazolidine Methylacetamide Oxazolidine Propionamide...

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Acetone imine

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Acetone imine, or 2-propanimine is an organic compound and an imine with the chemical formula (CH3)2CNH. It is a volatile and flammable liquid at room...

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Beckmann rearrangement

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accounting for solvent molecules and substituents. The rearrangement of acetone oxime in the Beckmann solution involved three acetic acid molecules and one...

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Methoxyamine

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example, it is obtained by O-methylation of acetone oxime followed by hydrolysis of the O-methylated oxime: (CH3)2CNOCH3 + H2O → (CH3)2CO + H2NOCH3 The...

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Ketone

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(which contains a carbon–oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula (CH3)2CO. Many ketones are...

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Eplivanserin

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enone), i.e. CID:53982926 (7). (2-chloroethyl)dimethylamine (CDMA) & acetone oxime are reacted together to give dimethylaminoacetoxime (DMA acetoxime)...

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Cyclohexanone

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cyclohexanone supply is converted to cyclohexanone oxime. In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon...

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Cilobamine

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reagent, and reduction of the oxime gives CID:154108204 (6). A reductive amination of the primary amino group with acetone then completed the synthesis...

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TEMPO

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Galli, C. (2009). "Nitroxyl radicals". Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids. Vol. 2. John Wiley & Sons. pp. 705–750. ISBN 978-0-470-51261-6...

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Hydrazone

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oximes". Angew. Chem. Int. Ed. 47 (39): 7523–6. doi:10.1002/anie.200802651. PMC 2743602. PMID 18712739. Day, A. C.; Whiting, M. C. (1970). "Acetone Hydrazone"...

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Nitrile

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also prepared by transcyanohydrin reactions starting, for example, with acetone cyanohydrin as a source of HCN. Nitriles can be prepared by the dehydration...

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Methyl group

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can be deprotonated. For example, the acidity of the methyl groups in acetone ((CH3)2CO) is about 1020 times more acidic than methane. The resulting...

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Organic peroxides

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Methyl ethyl ketone peroxide, benzoyl peroxide and to a smaller degree acetone peroxide are used as initiators for radical polymerization of some thermosets...

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Carbonyl group

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within a carbonyl compound decreases. The pKa values of acetaldehyde and acetone are 16.7 and 19 respectively, Infrared spectroscopy: the C=O double bond...

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Nitro compound

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laboratory by treating sodium chloroacetate with sodium nitrite. Oxidation of oximes or primary amines. Reduction of β-nitro alcohols or nitroalkenes. By decarboxylation...

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Alcohol oxidation

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pyridine, acetone or t-BuOH. KMnO4 reacts with many functional groups, such as secondary alcohols, 1,2-diols, aldehydes, alkenes, oximes, sulfides and...

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Benzonitrile

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laboratory it can be prepared by the dehydration of benzamide or benzaldehyde oxime or by the Rosenmund–von Braun reaction using cuprous cyanide or NaCN/DMSO...

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Ethyl acetate

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commonly used to clean circuit boards and in some nail varnish removers (acetone is also used). Coffee beans and tea leaves are decaffeinated with this...

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Acetal

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sometimes called a formal or the methylenedioxy group. The acetal formed from acetone is sometimes called an acetonide. Used in a more general sense, the term...

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Diflubenzuron

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Solubility in water 0.08 mg/L Solubility in other solvents DMSO: 12 g/100 g Acetone 0.615 g/100 g Methanol: 0.09 g/100 g Pharmacology ATCvet code QP53BC02...

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Cyclohexanol

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gives cyclohexanone, which is converted on a large scale in industry to the oxime, a precursor to caprolactam. As a laboratory exercise, this oxidation can...

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