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| CAS No.: | 95-45-4 |
|---|---|
| Name: | Dimethylglyoxime |
| Molecular Structure: | |
 |
|
| Formula: | C4H8N2O2 |
| Molecular Weight: | 116.12 |
| Synonyms: | 2,3-Butanedione,dioxime (8CI,9CI);2,3-Diisonitrosobutane;Biacetyl dioxime;Chugaev's reagent;2,3-Butanedione,2,3-dioxime;NSC 9;Reagents, Chugaev's;Diacetyl dioxime; |
| EINECS: | 202-420-1 |
| Density: | 1.17 g/cm3 |
| Melting Point: | 240-241 °C(lit.) |
| Boiling Point: | 271.529 °C at 760 mmHg |
| Flash Point: | 158.376 °C |
| Solubility: | insoluble in water |
| Appearance: | white crystalline powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22-20/21/22 |
| Safety: | 22-24/25-36 |
| Transport Information: | |
| PSA: | 65.18000 |
| LogP: | 0.68660 |
hydrogenchloride
A
triphenylantimony dichloride
B
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| In hydrogenchloride react. antimony compd. with concd. HCl; | A 99% B n/a |
| Conditions | Yield |
|---|---|
| With pyridine; hydroxylamine hydrochloride In methanol for 1h; Reflux; | 95% |
| With pyridine; hydroxylamine hydrochloride In methanol for 1h; Inert atmosphere; Reflux; | 92% |
butane-2,3-dione mono-oxime
A
2-(1-hydroxyiminoethyl)-2,4,5-trimethyl-2H-imidazole 1-oxide
B
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With ammonium carbonate In ethanol; water for 72h; Heating; | A 35% B 9.0 g |
| Conditions | Yield |
|---|---|
| With nitric acid In not given | A 32% B n/a |
| With HNO3 In not given | A 32% B n/a |
potassium cyanide
butane-2,3-dione mono-oxime
A
2-(1-hydroxyiminoethyl)-2,4,5-trimethyl-2H-imidazole 1-oxide
B
butane-2,3-dione dioxime
1-hydroxytetrahydro-4,5-dimethyl-2-oxoimidazole-4,5-dicarboxylic acid
(3aRS,6aSR)-6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethylpyrrolo<3,4-d>imidazole-2,4-dione
| Conditions | Yield |
|---|---|
| With ammonium carbonate; water In ethanol at 70℃; for 4h; Product distribution; Mechanism; | A 0.5 g B 0.07 g C 3% D 26.5% |
| With ammonium carbonate; water In ethanol at 70℃; for 4h; | A 0.5 g B 0.07 g C 3% D 26.5% |
potassium cyanide
butane-2,3-dione mono-oxime
(3aRS,6aSR)-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethyl-5H-pyrrolo<3,4-d>imidazole-2,4,6-trione
B
butane-2,3-dione dioxime
1-hydroxytetrahydro-4,5-dimethyl-2-oxoimidazole-4,5-dicarboxylic acid
(3aRS,6aSR)-6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethylpyrrolo<3,4-d>imidazole-2,4-dione
| Conditions | Yield |
|---|---|
| With ammonium carbonate; water In ethanol at 70℃; for 4h; | A 0.4 g B 0.07 g C 3% D 26.5% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide; water; sodium nitrite ueber mehrere Stufen; | |
| With sodium hydroxide dann versetzt mit Natriumnitrit und leitet Schwefeldioxyd ein; |
diacetyldioxime monomethylether
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With hydrogenchloride |
diacetyldioxime monomethylether
A
butane-2,3-dione-2-methoxime
B
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With hydrogenchloride at 60℃; |
2,3-dinitro-butane
butane-2,3-dione dioxime
ethyl methyl ketone oxime
butane-2,3-dione mono-oxime
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With sulfuric acid at 40℃; |
butane-2,3-dione mono-oxime
urea
A
tetrahydro-3a,6a-dimethylimidazo<4,5-d>imidazole-2,5-(1H,3H)-dione
B
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With ethanol; sulfuric acid |
butane-2,3-dione mono-oxime
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With hydroxylamine | |
| With acid solution; sodium hydroxylamine-O-sulfonate at 70℃; |
| Conditions | Yield |
|---|---|
| With hydrogenchloride at 40 - 50℃; ueber mehrere Stufen; |
| Conditions | Yield |
|---|---|
| With hydrogenchloride |
| Conditions | Yield |
|---|---|
| Darstellung; |
| Conditions | Yield |
|---|---|
| With titanium(IV) sulfate; titanium(III) sulphate; sulfuric acid at 32.85℃; Equilibrium constant; Reduction; |
6,7-dimethylquinoline
chloroform
ozone
A
pyrrolo[3,4-b]pyridine-5,7-dione dioxime
B
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| at -30℃; Beh. des Rktgem. mit Hydroxylamin-hydrochlorid und wss. Natriumcarbonat; |
2,3-dimethylquinoline
chloroform
ozone
A
glyoxime
B
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| at -40℃; anschl. mit Hydroxylamin-hydrochlorid und wss. Natriumcarbonat; |
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With hydroxylamine |
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With acetic acid; zinc |
| Conditions | Yield |
|---|---|
| With sodium carbonate |
butane-2,3-dione mono-oxime
butane-2,3-dione dioxime
hydrogenchloride
butane-2,3-dione mono-oxime
urea
A
butane-2,3-dione dioxime
sulfuric acid
butane-2,3-dione mono-oxime
urea
A
butane-2,3-dione dioxime
hydrogenchloride
ethanol
butane-2,3-dione mono-oxime
urea
A
butane-2,3-dione dioxime
ethanol
sulfuric acid
butane-2,3-dione mono-oxime
urea
A
butane-2,3-dione dioxime
bis(dipiperidinyldithiocarbamato)nickel(II)
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With ammonia In ethanol byproducts: C5H10NCS2NH4; addn. of aq. NH3 to a mixt. of nickel complex and ligand in EtOH, refluxing for 30 min; filtration, washing with ethanol, ether, drying in vac.; elem. anal.; | 100% |
(phthaloyl)bis(triphenylphosphino)(chloro)cobalt
butane-2,3-dione dioxime
(phthaloyl)(dimethylglyoxime)(triphenylphosphine)chloro-cobalt
| Conditions | Yield |
|---|---|
| In acetonitrile Co-complex, dimethylglyoxime, and MeCN were refluxed with stirring under an N2 atmosphere until all of the starting material had solubilized; soln. was cooled, MeCN removed, residue was triturated with Et2O; elem. anal.; | 100% |
bis(N,N-diethyldithiocarbamato)nickel(II)
butane-2,3-dione dioxime
Ni((CH3CH2)2NCS2)(CH3CNOCNOHCH3)
| Conditions | Yield |
|---|---|
| With ammonia In ethanol byproducts: (CH3CH2)2NCS2NH4; addn. of aq. NH3 to a mixt. of nickel complex and ligand in EtOH, refluxing for 30 min; filtration, washing with ethanol, ether, drying in vac.; elem. anal.; | 100% |
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With oxygen In acetone at 20℃; for 1h; Schlenk technique; Inert atmosphere; | 100% |
| With air In acetone for 0.333333h; Sealed tube; | 99% |
| In acetone for 0.166667h; | 79% |
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With oxygen In acetone at 20℃; for 1h; Schlenk technique; Inert atmosphere; | 100% |
rhenium(I) pentacarbonyl chloride
butane-2,3-dione dioxime
[ReCl(CO)3(dimethylglyoxime)]
| Conditions | Yield |
|---|---|
| In methanol Re complex was mixed with ligand (1 equiv.); MeOH was added; refluxed for 4 h; evapd.; elem. anal.; | 98% |
cis-dichlorobis(dimethylsulfoxide)platinum(II)
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With triethylamine In methanol for 2h; Reflux; | 97% |
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| In ethanol; water addn. of hot soln. of glyoxime in 95% aq. ethanol to boiling purple suspension of RhCl3; immediately discoloration of mixture to yellow; heating at reflux for 1 h; cooling to 0°C;; pptn.; drying;; | 96% |
| Conditions | Yield |
|---|---|
| In methanol Reflux; | 96% |
| Conditions | Yield |
|---|---|
| With potassium hydroxide; caesium carbonate In ethylene glycol at 110 - 160℃; | 95% |
| With succinic acid anhydride at 160℃; Neat (no solvent); | 30% |
| With potassium hydroxide In ethylene glycol at 160 - 190℃; |
| Conditions | Yield |
|---|---|
| In solid metal to ligand ratio 1:2, static load (10 MPa, shear angle 45-90°), contact time no more than 15 min; | 95% |
nickel diacetate
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| In solid metal to ligand ratio 1:2, static load (10 MPa, shear angle 45-90°), contact time no more than 15 min; | 95% |
| In ethanol in concd. soln.; short heating on water bath; filtration, multiple washing with alcohol; | |
| In ethanol in concd. soln.; short heating on water bath; filtration, multiple washing with alcohol; |
| Conditions | Yield |
|---|---|
| In solid metal to ligand ratio 1:2, static load (10 MPa, shear angle 45-90°), contact time no more than 15 min; | 95% |
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With H2SO4 In ethanol; water byproducts: H(1+); room temp.; addn. of aq. soln. of metal compd. (pH = 2.5, H2SO4) to soln. of ligand (in EtOH), stirring (pptn.); filtration, washing (H2O/EtOH = 1/1), drying (50°C); elem. anal.; | 95% |
| Conditions | Yield |
|---|---|
| In methanol addn. of CoCl2*6H2O in MeOH to dimethylglyoxime, heating (water bath), addn. of pyridine and MeOH soln. of InCl3*3H2O (ratio of Co/dioxime/In/amine 1:2:1:5, stirring), heating (stirring until substances dissolved); crystn. on cooling, filtration off, washing (MeOH, ether), drying (air); elem. anal.; | 94% |
pyridine
cobalt(II) diacetate tetrahydrate
acetic acid
butane-2,3-dione dioxime
phenyl propargyl ketone
(3-phenyl-1-propen-3-one-1-yl)(pyridine)bis(dimethylglyoximato)cobalt(III)
| Conditions | Yield |
|---|---|
| With Zn In tetrahydrofuran under N2, Co(CH3COO)2*4H2O, dimethylglyoxime, pyridine and zinc dust were all combined in THF and refluxed 15 min, cooled to 25°C, C6H5COCCH was added, the mixt. was refluxed for 1 h, the mixt. was cooled to 25°C, CH3COOH was added; the soln. was poured into ice water containing pyridine, the product was extd. with CH3CH2OCOCH3, dried (MgSO4), concd. (vac.), the solid was triturated with pentane/(CH3CH2)2O; elem. anal.; | 94% |
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With H2SO4 In ethanol; water byproducts: H(1+); room temp.; addn. of aq. soln. of metal compd. (pH = 4.0, H2SO4) to soln. of ligand (in EtOH), stirring (pptn.); filtration, washing (H2O/EtOH = 1/1), drying (50°C); elem. anal.; | 92% |
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| In acetonitrile 24 h/room temp.;; | 91% |
| In acetonitrile | 91% |
| Conditions | Yield |
|---|---|
| With pyridine; sodium hydroxide; hydrogen In methanol; water addn. of alkene to soln. of CoCl2*6H2O, dimethylglyoxime and pyridine in MeOH (room temp.), degassing (N2, 20 min), addn. of aq. NaOH, degassing (15 min), exchange of N2 for H2 (<1 h); addn. of H2O, extn. (CH2Cl2), drying (MgSO4), evapn., chromy (silica gel) and/or recrystn (CH2Cl2-petroleum ether); | 91% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide; sodium tetrahydroborate In methanol stirring CoCl2, glyoxime in CH3OH at -20°C under N2; addn. of 50% aq. NaOH soln., 3-bromo-4-methylpyridine, NaBH4 in CH3OH; stirring at 20°C for 1 h; addn. of bromide at -20, stirring at 20°C in dark for 14 h;; addn. of water containing 1 drop 3-bromo-4-methylpyridine to oily residue; pptn.; drying; elem. anal.; | 91% |
| Conditions | Yield |
|---|---|
| In methanol at 70℃; for 4h; Inert atmosphere; Schlenk technique; | 91% |
-butyl vinyl ether
butane-2,3-dione dioxime
dimethylglyoxal O,O'-di(1-butoxyethyl)dioxime
| Conditions | Yield |
|---|---|
| With hydrogen bromide In diethyl ether at 25℃; for 48h; | 90% |
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| In methanol stirring for 5 min; concn. and layering with ether; elem. anal.; | 90% |
| Conditions | Yield |
|---|---|
| In water dimetylglyoxime added to suspn. of UO3 in H2O; mixt. stirred under heating for 6 h (molar ratio U:C4H8N2O2 = 1:1.23); ppt. filtered off; washed (H2O, EtOH, ether); dried on filter in air flow; elem. anal.; | 90% |
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| In acetonitrile 24 h/room temp.;; | 90% |
| In acetonitrile | 90% |
| Conditions | Yield |
|---|---|
| With perhydrol In water heating mixture of CoCl2*6H2O and powdered dimethylglyoxime in H2O on a water-bath; addn. of perhydrol under stirring; addn. of excess HCl-soln. to the warm soln.;; washing with dild. HCl-soln., alcohol and ether;; | 90% |
butane-2,3-dione dioxime
| Conditions | Yield |
|---|---|
| With ammonium acetate In water heating all compounds in a sealed tube (10 hours/150 °C);; filtration; evapn. of the filtrate to dryness; washing (alc.); recrystn. from hot water;; | 90% |
| Conditions | Yield |
|---|---|
| In methanol addn. of CoCl2*6H2O in MeOH to dimethylglyoxime, heating (water bath), addn. of pyridine and MeOH soln. of InCl3*3H2O (ratio of Co/dioxime/In/amine 1:2:1:5, stirring), heating (stirring until substances dissolved); crystn. on cooling, filtration off, washing (MeOH, ether), drying (air); elem. anal.; | 90% |
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IUPAC Name: N-[(Z)-3-nitrosobut-2-en-2-yl]hydroxylamine
Molecular formula: C4H8N2O2
Molar mass: 116.12 g/mol
Appearance: White/Off White Powder
Index of Refraction: 1.487
Molar Refractivity: 28.417 cm3
Molar Volume: 98.819 cm3
Polarizability: 11.265× 10-24cm3
Surface Tension: 37.538 dyne/cm
Density: 1.175 g/cm3
Flash Point: 158.376 °C
Enthalpy of Vaporization: 59.186 kJ/mol
Melting point: 240 - 241 °C
Boiling Point: 271.529 °C at 760 mmHg
Vapour Pressure: 0.001 mmHg at 25°C
Storage temp.: 2-8°C
Solubility in water: low
Stability: Stable. Incompatible with strong oxidizing agents.
Other names: Dimethylglyoxime,Diacetyl dioxime,Chugaev's Reagent 2,3-diisonitrosobutane
The Structure of Diacetyl dioxime (95-45-4):
Diacetyl dioxime (95-45-4) is used in the analysis of palladium or nickel.
Diacetyl dioxime (95-45-4) is used as a chelating agent in the gravimetric analysis of nickel.
Diacetyl dioxime (95-45-4) can be prepared from butanone first by reaction with ethylnitrite followed by conversion of the biacetyl monoxime using sodium hydroxylamine monosulfonate:
| 1. | otr-ham:emb 100 µg/L | FCTXAV Food and Cosmetics Toxicology. 18 (1980),289. | ||
| 2. | orl-rat LDLo:250 mg/kg | NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. 5 (1953),26. |
Reported in EPA TSCA Inventory.
Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: 
Xn
Risk Statements: 22-20/21/22
22: Harmful if swallowed
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 22-24/25-36
22: Do not breathe dust
24/25: Avoid contact with skin and eyes
36: Wear suitable protective clothing
WGK Germany: 3
RTECS: EK2975000
F: 10: Keep under argon.
Hazard Note: Harmful
HS Code: 29280090
1. First Aid Measures
Ingestion:
Induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Skin:
Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. Wash clothing before reuse.
Eyes:
Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
2. Handling and Storage
Storage:
Keep away from heat and flame. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
