Dimethylglyoxime

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Dimethylglyoxime is a chemical compound described by the formula CH3C(NOH)C(NOH)CH3. Its abbreviation is dmgH2 for neutral form, and dmgH for anionic form, where H stands for hydrogen. This colourless solid is the dioxime derivative of the diketone butane-2,3-dione (also known as diacetyl). DmgH2 is used in the analysis of palladium or nickel. Its coordination complexes are of theoretical interest as models for enzymes and as catalysts. Many related ligands can be prepared from other diketones, e.g. benzil.



Preparation


Dimethylglyoxime can be prepared from butanone first by reaction with ethyl nitrite to give biacetyl monoxime. The second oxime is installed using sodium hydroxylamine monosulfonate:[1]


Preparation of dimethylglyoxime.png



Complexes


Dimethylglyoxime is used to detect and quantify nickel, which forms the bright red complex nickel bis(dimethylglyoximate) (Ni(dmgH)2). The reaction was discovered by L. A. Chugaev in 1905.[2]


Reaction of Ni-dmg-Formation         Formation of the red complex


Cobalt complexes have also received much attention. In chloro(pyridine)cobaloxime[3] the macrocycle [dmgH]22− mimics the macrocyclic ligand found in vitamin B12.




Structure of chloro(pyridine)cobaloxime.


References




  1. ^ Semon, W. L.; Damerell, V. R. (1930). "Dimethylglyoxime". Organic Syntheses. 10: 22. doi:10.15227/orgsyn.010.0022.CS1 maint: Multiple names: authors list (link).mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em


  2. ^ Lev Tschugaeff (1905). "Über ein neues, empfindliches Reagens auf Nickel". Berichte der deutschen chemischen Gesellschaft. 38 (3): 2520–2522. doi:10.1002/cber.19050380317.


  3. ^ Girolami, G.. S.; Rauchfuss, T.B.; Angelici, R. J. (1999). Synthesis and Technique in Inorganic Chemistry: A Laboratory Manual (3rd ed.). pp. 213–215.



Dimethylglyoxime

Dimethylglyoxime

Dimethylglyoxime-3D-balls.png
Names

IUPAC name

N,N′-Dihydroxy-2,3-butanediimine

Other names
  • Dimethylglyoxime

  • Diacetyl dioxime

  • Butane-2,3-dioxime

  • Chugaev's reagent


Identifiers

CAS Number



  • 95-45-4 ☑Y


3D model (JSmol)


  • Interactive image


ChEMBL

  • ChEMBL3184098


ChemSpider


  • 10606175 ☑Y


ECHA InfoCard

100.002.201

EC Number
202-420-1


PubChem CID


  • 5356010


RTECS number
EK2975000

UNII


  • 2971MFT1KY ☑Y





Properties

Chemical formula


C4H8N2O2

Molar mass
116.12 g·mol−1
Appearance
White/Off White Powder

Density
1.37 g/cm3

Melting point
 240 to 241 °C (464 to 466 °F; 513 to 514 K)

Boiling point
decomposes

Solubility in water

low
Structure

Dipole moment

0
Hazards
Main hazards
Toxic, Skin/Eye Irritant

Safety data sheet

External MSDS

GHS pictograms

The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)

GHS signal word
Danger

GHS hazard statements


H228, H301

GHS precautionary statements


P210, P240, P241, P264, P270, P280, P301+310, P321, P330, P370+378, P405, P501

NFPA 704



Flammability (red): no hazard codeHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity (yellow): no hazard codeSpecial hazards (white): no codeNFPA 704 four-colored diamond



2





Related compounds

Related compounds


Hydroxylamine
salicylaldoxime

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


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Infobox references





Authority control Edit this at Wikidata

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