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Dimethylglyoxime

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.

Dimethylglyoxime
Names
IUPAC name
N,N-Dihydroxy-2,3-butanediimine
Other names
  • Dimethylglyoxime
  • Diacetyl dioxime
  • Butane-2,3-dioxime
  • Chugaev's reagent
Identifiers
  • 95-45-4 Y
  • 17117-97-4 (E) Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL3184098
ChemSpider
  • 10606175 Y
ECHA InfoCard 100.002.201
EC Number
  • 202-420-1
  • 5356010
RTECS number
  • EK2975000
UNII
  • 2971MFT1KY Y
  • DTXSID2044393
  • InChI=1S/C4H8N2O2/c1-3(5-7)4(2)6-8/h7-8H,1-2H3/b5-3-,6-4+ Y
    Key: JGUQDUKBUKFFRO-CIIODKQPSA-N Y
  • InChI=1/C4H8N2O2/c1-3(5-7)4(2)6-8/h7-8H,1-2H3/b5-3-,6-4+
    Key: JGUQDUKBUKFFRO-CIIODKQPBA
  • C\C(=N\O)\C(\C)=N\O
Properties
C4H8N2O2
Molar mass 116.120 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
low
Structure
0
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic, Skin/Eye Irritant
GHS labelling:
Danger
H228, H301
P210, P240, P241, P264, P270, P280, P301+P310, P321, P330, P370+P378, P405, P501
NFPA 704 (fire diamond)
Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability (red): no hazard codeInstability (yellow): no hazard codeSpecial hazards (white): no code
2
Safety data sheet (SDS) External MSDS
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).
Y verify (what is YN ?)

Preparation Edit

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]

 

Complexes Edit

Dimethylglyoxime forms complexes with metals including nickel,[2] palladium and cobalt.[3] These complexes are used to separate those cations from solutions of metal salts and in gravimetric analysis. It is also used in precious metals refining to precipitate palladium from solutions of palladium chloride.

References Edit

  1. ^ Semon, W. L.; Damerell, V. R. (1930). "Dimethylglyoxime". Organic Syntheses. 10: 22. doi:10.15227/orgsyn.010.0022.
  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, chemical, compound, described, formula, ch3c, abbreviation, dmgh2, neutral, form, dmgh, anionic, form, where, stands, hydrogen, this, colourless, solid, dioxime, derivative, diketone, butane, dione, also, known, diacetyl, dmgh2, used, analysi. 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 Dimethylglyoxime NamesIUPAC name N N Dihydroxy 2 3 butanediimineOther names DimethylglyoximeDiacetyl dioximeButane 2 3 dioximeChugaev s reagentIdentifiersCAS Number 95 45 4 Y17117 97 4 E Y3D model JSmol Interactive imageChEMBL ChEMBL3184098ChemSpider 10606175 YECHA InfoCard 100 002 201EC Number 202 420 1PubChem CID 5356010RTECS number EK2975000UNII 2971MFT1KY YCompTox Dashboard EPA DTXSID2044393InChI InChI 1S C4H8N2O2 c1 3 5 7 4 2 6 8 h7 8H 1 2H3 b5 3 6 4 YKey JGUQDUKBUKFFRO CIIODKQPSA N YInChI 1 C4H8N2O2 c1 3 5 7 4 2 6 8 h7 8H 1 2H3 b5 3 6 4 Key JGUQDUKBUKFFRO CIIODKQPBASMILES C C N O C C N OPropertiesChemical formula C 4H 8N 2O 2Molar mass 116 120 g mol 1Appearance White Off White PowderDensity 1 37 g cm3Melting point 240 to 241 C 464 to 466 F 513 to 514 K Boiling point decomposesSolubility in water lowStructureDipole moment 0HazardsOccupational safety and health OHS OSH Main hazards Toxic Skin Eye IrritantGHS labelling PictogramsSignal word DangerHazard statements H228 H301Precautionary statements P210 P240 P241 P264 P270 P280 P301 P310 P321 P330 P370 P378 P405 P501NFPA 704 fire diamond 2Safety data sheet SDS External MSDSRelated compoundsRelated compounds HydroxylaminesalicylaldoximeExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox referencesPreparation EditDimethylglyoxime 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 Complexes EditDimethylglyoxime forms complexes with metals including nickel 2 palladium and cobalt 3 These complexes are used to separate those cations from solutions of metal salts and in gravimetric analysis It is also used in precious metals refining to precipitate palladium from solutions of palladium chloride Dimethylglyoxime Complexes Reaction of Ni dmg Formation Sample of Ni dmgH 2 Structure of chloro pyridine cobaloximeReferences Edit Semon W L Damerell V R 1930 Dimethylglyoxime Organic Syntheses 10 22 doi 10 15227 orgsyn 010 0022 Lev Tschugaeff 1905 Uber ein neues empfindliches Reagens auf Nickel Berichte der Deutschen Chemischen Gesellschaft 38 3 2520 2522 doi 10 1002 cber 19050380317 Girolami G S Rauchfuss T B Angelici R J 1999 Synthesis and Technique in Inorganic Chemistry A Laboratory Manual 3rd ed pp 213 215 Retrieved from https en wikipedia org w index php title Dimethylglyoxime amp oldid 1164891353 Cobaloximes, wikipedia, wiki, book, books, library,

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